How to Style an Oversized Shirt: Types, Tips & Outfit Ideas

How to style an oversized shirt - faverie

If you have been in a women’s clothing store lately or been shopping for women’s clothing online, then you have probably noticed many oversized shirts for sale. You may have shied away from these shirts, fearing that they would not look great on you. This post will help you overcome that fear by showing you How to Style an Oversized Shirt.

After answering some general questions, I will lead you through a discussion of the many options available. Along the way, I will suggest numerous ways that you will want to wear oversized shirts. Then, I will tell you some tips to help you look fabulous while wearing them.

Let’s get started because after you read this post, you will want to hustle to add many oversized shirts to your wardrobe.

Oversized shirts FAQ

Wearing an oversized shirt is one of the hottest fashion trends right now. One of the reasons is that there are so many comfortable choices available that will look great on you.

Many ladies have fond memories of slipping into their parent’s shirts as a child while playing dress-up, allowing them to feel that same love. Wearing oversized shirts is a fashion trend that is not going away. So you will want several choices in your wardrobe.

The trend of wearing oversized clothing started shortly after World War I as women won the right to vote. While it had been fashionable during the war to wear tight-fitting clothing, women chose to start wearing more comfortable clothing that they could easily move in. 

During the Great Depression, women found ways to add more fabric to their outfits to keep them in great shape so that they did not have to replace them.

Oversized fashion especially took off after World War II when Christian Dior introduced the New Look. He replaced his New Look with his Corelle line in the 1950s, and everyone soon copied the boxy look.

Let’s learn more about oversized shirts!

What are oversized shirts?

Oversized shirts are boxy shirts that end below the waistline. They have an extremely loose fit making them ultra-comfortable to wear. These pieces are deliberately designed to be big. While some are one-size-fits-all if you look at clothing that is not, be sure to buy it in your normal size.

While I will go into much more detail in the next chapter, there are many types of oversized shirts. Manufacturers make these shirts from a variety of fabrics. 

While cotton is a prevalent choice, you can also find options made from polyester, rayon, and other materials. The key is that they have a very boxy appearance and are large on the person wearing them.

You can also find different types of sleeves on oversized clothing. Some have batwing sleeves, where the sleeves are extremely wide at the shoulders and narrow to a tight-fitting wrist. 

Chica camisa blanca clara y un vestido floral se encuentra pensativamente en la orilla del rio

Others have sleeves that you can roll up, which are a great choice when the weather cannot decide what it wants to do.

One thing that all oversized shirts have in common is that they are long, and they come to at least below the waist, and many shirts come almost to the knees. 

This is an excellent advantage for those who are longer in the back because they do not have to worry about their shirt riding up and showing their unmentionables.

You can find oversized shirts in many colors. While most options are solid-colored, you can also find beautiful patterns. Since most are designed for casual wear, colors are usually kept light. 

Still, black and other neutral colors are available. So you can easily wear an oversized shirt with many bottoms or, in some cases, no bottom at all.

When can you wear oversized shirts?

You can wear oversized shirts to almost any occasion if you choose one made from a suitable fabric. Silky oversized shirts are ideal for semi-formal occasions, while those made from flannel and other similar materials are perfect for casual wear, especially in the wintertime. Some linen and cotton options can be worn to work, especially in small-and-mid-sized businesses.

An oversized shirt is perfect for many office environments. Choose one in a color that is appropriate for your office and wear it with a pair of matching heels. Then, carry a matching handbag to create a monochromatic outfit that will get you noticed. This outfit also works great for going out for drinks after work or running errands around town.

Another fabulous choice is to wear an oversized shirt with a crop top and tie the two together. Then, wear a pair of high-waisted pants with a pattern. This is an excellent look for a casual date.

It is also easy to create an athletic-looking outfit with an oversized shirt. Pair it with a muscle shirt and your leather joggers or baggy trousers. Then, slip into your favorite sneakers.

The most traditional way to wear an oversized shirt is with your skinny jeans. Therefore, you can easily wear it anywhere you can wear jeans. This is a great look to wear to the farmers’ market or a country weekend getaway.

Consider wearing your oversized shirt with matching trousers. Then, leave the shirt open to reveal a crop top underneath. This is a fantastic look for lazy Sunday morning brunches.

Are oversized shirts in vogue this year?

Wearing oversized shirts has been trendy since the 1920s. Therefore, they are a safe bet to be in vogue this year and next. Consequently, you can be assured that you can wear your high-quality oversized shirt for many occasions now and far into the future.

The vast number of ways you can wear an oversized shirt helps ensure that you can wear them with other trendy clothes. For example, you can easily pair it with a skirt. This is especially great when you wear an oversized graphic tee and a solid-colored skirt that picks up on one of the colors in the t-shirt.

Oversized shirts are ideal for wearing over leggings. Give your outfit extra pizzazz by wrapping a sweater around your shoulders. If leggings are against the dress code, then trade them out for a pair of high-waisted trousers or your skinny jeans.

You can easily create different looks when you wear an oversized shirt as a dress. Throw on a pair of cowboy boots, and you have the perfect western-inspired outfit. Wear an oversized shirt with your heels and conservative makeup to create a darling outfit to wear to work.

Step back in time by wearing an oversized shirt open over a tight-fitting graphic tee. Then, wear your Spandex pants and your platform shoes to create an outfit straight out of the 1980s. Alternatively, an oversized skirt is an excellent option for wearing to a Roaring 20s party when you pair it with men’s pants and a cloche hat to create a boyish profile.

Who can wear oversized shirts?

Everyone can easily wear an oversized shirt. They are ideal for making smaller and thinner women look more substantial. They also are great for larger women who want to camouflage their curves. The key is how you style an outfit to look best on your body silhouette.

Woman reading book dark outfit

If you have long legs, consider pairing an oversized graphic t-shirt with a mini skirt. If you want to, you can roll up the sleeves a little bit to give the outfit a trendier appearance.

Oversized shirts are ideal for women with square and rectangular body shapes because you have broad shoulders to act as a great anchor. Try to avoid those made from stiff fabric as they will make you look bigger.

An oversized shirt worn open is a great way to balance your look if you are an inverted triangle. Avoid shirts with straight necklines, but V, round, and scoop necklines look great on you. Oversized shirts are a great option because they end below your waist.

A woman with an hourglass figure looks terrific in oversized shirt dresses. Choose an option with a belt at the waist, or add one to create a focal point and show off your curves. You can also tuck in the shirt and wear it with a skirt or skinny jeans.

An excellent choice for a pear-shaped woman is to wear an oversized blouse over a crop top. Options that hang a little bit away from your body are ideal because they help balance your look. This is also a great body shape to wear oversized shirts with batwing sleeves because they help balance your look.

A woman with an apple shape looks fabulous in oversized shirts that end below the hip. They also look great when a vest or blazer is added over the shirt.

What shoes can you wear with oversized shirts?

Depending on how you stylize the outfit, you can wear almost any type of shoe with an oversized shirt. With so many different styling options, oversized shirts are perfect for wearing with every shoe, from high heels to go-go boots.

An oversized shirt and biker shorts are perfect for an early morning bike ride when you wear them with your sneakers. Later in the day, wear your favorite oversized shirt with your athletic shorts and trainers for a run. Then, wear a short skirt with your oversized shirt and a pair of slip-on sneakers for a casual dinner date.

Consider wearing a belted, oversized shirt dress with your favorite pumps when heading to work. You can also wear the shirt with your closed-toed high-heeled sandals. After work, change over to your ballet flats as they will be easier to walk in.

There are many other shoe options that you may want to consider when wearing an oversized shirt during your leisure time. They make a perfect swimsuit coverup when paired with flat sandals and worn to the beach or a pool party. 

If you are going to enjoy a weekend in the country, consider wearing the shirt with a pair of western boots, especially if you are going line dancing. Alternatively, an oversized shirt looks great when paired with thigh-high boots and a mini skirt for a night of clubbing.

An oversized shirt is ideal for pairing with your favorite shoes while on vacation. You can easily wear an oversized shirt dress with a pair of boat shoes while having fun on the water. 

Pairing your shirt with leotards and a good pair of hiking boots makes them ideal for the trail. You may also want to wear the shirt with your mocassins when lounging by a fire pit or campfire.

What accessories can you wear with oversized shirts?

Since these shirts are big, you should stick with smaller accessories, or you will look too big. This is especially true regarding the upper part of your body. You will also want to carry a small handbag or tote so that you do not look even wider.

As I have already mentioned, a belt is a perfect accessory to add to an oversized shirt. Wear a narrow belt if you have slim hips that you want to accentuate. If your hips are wider, but you still want to pull in the shirt, choose a wider belt and wear it right under your bust.

Since an oversized shirt tends to draw attention upward, consider wearing a sparkly ankle bracelet or an anklet and toe ring set to help balance your body. Additionally, while not a fashion accessory, you may want to wear playful socks or colored tights to balance your look.

Small earrings, like studs, are a great choice because you are already wider on the upper part of your body. Avoid earrings that hang further out than your shoulders, or you will look even bigger.

Depending on the look that you are trying to achieve, clips and ribbons in your hair can be a fantastic choice. You can wear them on the back or the side of your head, depending on your hairstyle.

You will want to stick to a smaller handbag style. A crossbody bag can be a terrific choice when worn with an oversized shirt because it can help break up the shirt’s shape and add visual interest to your wardrobe. 

A clutch can be a fantastic choice if you are headed out for a night on the town. If you are going to the beach, consider a small striped handbag that ends above your waist.

If you found yourself wanting to scream at me to give you more specific ideas about how to create outfits with oversized shirts, then the next chapter is perfect for you. 

We will examine many types of oversized shirts and how to style them. Therefore, you will want to keep reading. You will not want to miss these individual suggestions, and you may even find some you want to pass on to a friend.

Types of oversized shirts and how to wear them

I gave you a lot of general information in the last chapter about how to wear oversized shirts. In this chapter, I will tell you about the many types of oversized shirts on the market.

I am sure you will want to add many of these to your wardrobe after learning about them. So often, people picture an oversized t-shirt or an oversized button-up, but many other choices are available.

Think about all the different ways that women can wear oversized shirts. They are super to wear to the gym because you ensure you stay covered. They also make great shirts to wear on a casual date because of the wide variety of bottoms you can pair with effortlessly. 

If the beach or pool is calling your name, you can easily wear them as a coverup. They also make fabulous dresses to wear to the office with your favorite heels.

As you read through this list, picture yourself wearing each of these shirts to somewhere you go regularly.

Oversized shirt dress

Often called a shirtdress, these dresses borrow many details from men’s dress shirts. Manufacturers design most for women to wear a belt at the waist, and many have a collar like on a man’s dress shirt. Additionally, manufacturers make most from stiffer fabrics.

Woman walking street sunglasses bag

An oversized shirt dress is ideal for wearing to the office. Since the top of these dresses resembles a man’s shirt, they are ideal for wearing with a blazer. Then, carry a laptop or hobo bag, depending on your needs. Wear your black closed-toe pumps with this outfit. Choose simple jewelry that compliments the dress’ color.

A shirtdress is also an excellent choice for wearing on a casual date. Look for an option where you can roll up the sleeves to give it a relaxed vibe. Then, put on your favorite flat sandals. A necklace following the dress’s neckline may be all the jewelry you need.

Oversized flannel shirt

As the name suggests, an oversized flannel shirt is flannel. These shirts usually button up the front, and they are a great choice when the weather cannot decide what it wants to do because they are ideal for wearing over a graphic t-shirt.

For an outdoor hiking adventure, consider wearing an oversized flannel shirt over a graphic t-shirt. You will stay warmer if you choose darker colors. Then, pair them with your favorite jeans. Skinny ones are usually the best option if you want to look stylish on the trail. Do not forget your socks and hiking boots.

An oversized flannel shirt is an excellent option if you are going to a 1980s party. Opt to wear it over a graphic t-shirt. Choose one from your favorite boy band, or opt for one with a classic cartoon character on it. Then, wear your skinny jeans. Dr. Martens or similar work boots are a great footwear option.

Oversized plaid shirt

Manufacturers make oversized plaid shirts from various fabrics, and the plaid design can be of different sizes. Tartan plaids are often considered Swiss plaid and have different-sized squares throughout the shirt. 

Woman posing outdoors sunglasses oversized shirt

Gingham plaid has uniformed squares throughout, but some of them have a lighter color because of the way manufacturers weave the yarns to make the pattern. A checkered plaid usually only has white and colored squares. 

Another popular choice is houndstooth, where the plaid has sharp edges. There are also windowpane, Madras, and glen plaids if you are looking for something a little different.

One popular way to wear an oversized plaid shirt is with your skinny white jeans and western boots. Alternatively, consider pairing it with a denim skirt and your boots. This outfit looks particularly great when you wear it on a country weekend getaway.

Oversized long sleeve shirt

An oversized long-sleeve shirt is a fantastic option that you can dress up or down. Manufacturers use different fabrics, so consider a silkier option if you are going to dress it up or an option with more texture if you are going to dress it down.

A silky oversized long-sleeve shirt is an excellent option for wearing to work in most office environments. I particularly like to choose a light-colored one and wear it over a pair of neutral-colored leggings. 

Then, I add a belt and a conservative necklace. This looks super when your leggings end about your ankles, and you wear it with ballet flats matching the shirt’s color.

If you are headed out the door to run errands, a cotton oversized long-sleeved shirt can be an ideal choice. Pair it with your favorite skinny jeans and your sneakers.

Oversized button-up shirt

An oversized button-up shirt is an extremely flexible option. You can find short-and-long-sleeved options made from various materials. Additionally, you can find these shirts in many different colors and patterns.

You may want to pair it with your favorite dark denim jeans. Mid-or-high-rise options are ideal if you want your legs to look longer. I especially like this look when you leave the shirt unbuttoned most of the way up and wear it with a statement necklace. You will also want to wear the shirt tucked in and hold your pants up with a simple belt.

An oversized button-up shirt set is an ideal choice if you go to the beach. Choose a lightweight fabric so that you will stay cooler. Options that wick away moisture and dry quickly are perfect. The shirt will perfectly match your bottoms by buying it in a set. Then, wear it over your bikini.

Oversized denim shirt

An oversized denim shirt usually buttons up the front, but other styles are available. These shirts are generally a solid color, and they can be any color of denim.

One terrific outfit idea is to wear a button-up denim skirt with a khaki skirt and a stylish loose belt with a western design. 

Choose a thin belt that you can add just below your bust if you want to make your legs look longer or if you want to camouflage your stomach, add one below your natural waistline. Then, wear it with your stilettos.

Denim on denim is another great option if your two pieces of denim are far enough apart that they do not clash. You can wear the top tucked into your jeans in the front if you want, or wear the denim shirt with a denim skirt. You can opt to wear your flat shoes or your western boots.

Oversized gym shirt

An oversized gym shirt is a terrific exercise option as it provides extra coverage while staying close to your body. If you are afraid it might get caught in the exercise equipment, you can always stuff it into your shorts.

Oversized gym shirts are a fantastic option for a bike ride, in addition to wearing them to the gym. In that case, you will want to wear it with your biker shorts. Wearing a bright-colored oversized shirt helps ensure that motorists can see you. 

You may wish to wear biker shorts that have the same color down their sides as your shirt. Then, wear them both with your cycling shoes.

Another fantastic option is to wear your oversized gym shirt with your jogging pants. Consider shirts that have UV protection built into them along with cooling technology. This is a terrific choice to wear with your running shoes.

Oversized dress shirt

An oversized dress shirt can either button up the front or pull on over the head. Manufacturers usually make these shirts from smooth material, and they can have long-or-short sleeves.

An oversized dress shirt is a fabulous option when worn with a pair of high-waisted trousers if you want to elongate your upper body. This look works well in many business environments if you choose a white blouse and a neutral color of trousers, like navy blue. 

Then, wear a simple gold or silver necklace and matching earrings. Put your closed-toe shoes on. If the weather is cooler, consider wearing this outfit with a cardigan.

Another fabulous choice is to wear the dress shirt as a dress with a belt. This can be a fantastic choice for a night out on the town when you pair it with your favorite thigh-high boots. Then, wear your sparkly jewelry to complete the look.

Oversized short sleeve shirt

You can find many styles of short-sleeved oversized shirts. Therefore, you can choose options you can easily dress up or down. These shirts often make fabulous summertime dresses, but there are many other possibilities.

Pairing your oversized short-sleeved shirt with your leather joggers can be a marvelous plan. Consider choosing a shirt the same color as your joggers to create a monochromatic outfit. Ideally, your joggers will end about your ankles. Then, add a colorful pair of closed-toe pumps and a matching shoulder bag to give your outfit a pop of color.

A silky oversized shirt with short sleeves is an ideal option for the office when you pair them with your high-waisted dress trousers. Wear the combination with an unstructured blazer in a coordinating color. 

Remember that 60% of your outfit should be one color and 30% another. Then, choose colorful jewelry. For example, if you wear a red shirt, pair it with brown trousers and add yellow-green jewelry.

Oversized hip-hop shirt

Show the world that you are a hip-hop fan by wearing an oversized hip-hop shirt. You can choose one with your favorite band’s logo or photo on the front or back. These shirts come in various colors, so you can easily find one that is ideal for you.

A great way to wear your oversized hip-hop shirt is with baggy white cargo pants. Then, wear a denim jacket that ends about your waist with the outfit. You can have fun with this look by adding a belt and chains to the cargo pants. Doc Martens are a fabulous choice for your feet.

You may also want to pair your shirt with low-slung jeans and a crop top. Then, wear a hip-hop shirt that buttons up the front like a jacket. This is a fabulous choice for wearing with high-top tennis shoes. If they stay on your feet without their laces, then wear them that way.

Oversized stripes shirt

An oversized striped shirt is a terrific option that you can wear in many ways. Vertical stripes will make you look taller, while horizontal stripes will make you look wider.

Detail woman shoulder shirt

Choosing horizontal stipes that are close together will make you appear skinnier. If you have a fabulous chest, consider a striped shirt with only stripes in that area, as it will draw a viewer’s attention to that feature.

A simple way to wear an oversized striped shirt is with your skinny jeans. Choose a pair that stops about your ankles so that you can wear your ankle-high boots. A great choice is to wear black boots. Then, wear a few pieces of jewelry that match one of the shirt’s stripes. A black crossbody bag is a fantastic choice to carry.

An oversized striped shirt also looks fantastic with a denim skirt. Choose one that has a bit of flair to it. Then, pair it with your ballet flats or your flat sandals. You can tuck in the front and leave out the back to add visual interest to your outfit. This look works well with almost any type of shoe, so consider where you are going.

Oversized batwing sleeves shirt

If you are looking for a long-sleeved shirt with an unusual cut, you will fall in love with an oversized batwing-sleeve shirt. These shirts have extremely deep-cut armholes, and the sleeves gradually get smaller, so they taper at the wrist.

Consider wearing a batwing-sleeved shirt with your leggings. You can opt to wear it as an overshirt and wear a cowl-neck shirt underneath. This warm look will keep you cozy on a fall day. Keep the comfort level high by pairing it with your flats while running errands or relaxing at home.

While most batwing-sleeve shirts are long-sleeved, you can find short-sleeve options that look like a tunic. These shirts are ideal for pairing with a pair of mid-length shorts. Then, wear the outfit with your favorite sneakers. Low-cut canvas ones are a great option.

Oversized printed shirt

While oversized shirts are often in a single color, you can find printed ones. Remember, the smaller that you are, the bigger pattern that you can wear. If you choose an option with a big pattern, then consider wearing the same pattern in a smaller print somewhere else on your body. A headband with the same print is a great choice.

An oversized printed shirt is a fantastic option with neutral-colored trousers. Opt for tailored ones so that they stay close to your body. Then, wear your closed-toe pumps if you are heading to work.

Another fantastic option is to wear a shirt with a pencil skirt. Wear colored tights that match the skirt if the weather is cooler. An excellent choice for a skirt is one in a split complementary color to one of the primary colors in the shirt. 

This outfit looks super cute when worn with your closed-toe shoes to the office or your ankle boots for a casual date.

Plain white oversized shirt

A plain white oversized shirt is a fantastic option in the summer because it reflects all the sun’s rays, so it helps to keep you cooler. You can find oversized white shirts in many different styles so that you can put together many outfits.

You may want to consider wearing the shirt as a dress. Then, add a colorful belt. Opt for shoes and a bag that matches the color of your belt. A crossbody bag is a terrific option as it helps to break up the white and can add some definition to your body.

Wearing an oversized white shirt with your favorite patterned pants is another fantastic option. You should choose a pair that has the same shade of white in them. Then, wear your white sneakers. 

You can carry a white handbag or choose one that matches one of the colors in your pants. You will also want to add fun, colorful jewelry, such as a statement necklace.

Tie-dye oversized shirt

Woman wearing tie dye oversized shirt

You can buy a tie-dye oversized shirt or make your own as an art project at home from an oversized white t-shirt. Since they are a very colorful option, you will want to wear them with a neutral. Since the shirt is boldly colored, keep the rest of your outfit simple.

For example, an oversized tie-dyed shirt will look fantastic with your khaki chinos. Since this is a casual outfit, put on your favorite cross-trainers. There is no need for a necklace, but you can wear colorful earrings matching one of the colors on your shirt.

Another terrific option is to wear your oversized tye-dye t-shirt with a pair of denim shorts. You can give your outfit a 1980s vibe by wearing it with a casual-style beanie and your platform sandals. Again, jewelry is unnecessary, but you may want to wear a leather cord ankle bracelet.

Loose oversized shirt

Most oversized shirts are loose but choosing one that is exceptionally loose is a great way to go if you are looking for a casual look. These shirts are perfect as overshirts or use them as a coverup.

If going to the beach or the pool, a loose oversized shirt is ideal for wearing over your bikini or swimsuit. Choose one that buttons part way up that coordinate with your swimwear. Then, let your swimwear peek out of the opening. Flat sandals or water shoes are perfect for wearing with this outfit.

If you must stay where it is dry, then a loose oversized shirt is an ideal choice for wearing with a crop top. You can wear it with your favorite sneakers. Choose to keep the look simple by pairing them with your denim cutoffs. You can add a unique twist to your outfit by wearing colorful hair accessories or a hat.

Black oversized shirt

An oversized black shirt is ideal for wearing with many different outfits. Since black is a neutral color, you can opt to wear it with many different colored bottoms. Jeans and chinos are both outstanding choices. But you can also pair it with your favorite shorts and skirts.

One of my favorites is to pair an oversized black shirt with leopard-print leggings. Then, wear them with black high-heel sandals. I like to break the black up by wearing a statement necklace that draws on the same colors as the skirt. You can add a leopard-print belt to this outfit but ensure all your leopard prints look similar.

An oversized black shirt is also an excellent choice for wearing with stonewashed jeans and your sneakers. I love wearing colorful sneakers with this look. Then, carrying a crossbody bag of the same color. This looks especially great when worn with your sunglasses to an outdoor event.

Pink oversized shirt

You can wear pink with black to give it a sophisticated vibe or pair it with yellow-green to keep the look more natural. Of course, pink goes fantastic with neutral colors, like beige, so you will want to add an oversized pink shirt to your wardrobe.

Mujer caucasica joven pensativa en camisa rosa de gran tamano de pie con las manos entrelazadas contra backgr gris

An oversized pink shirt is an excellent option for wearing over a white camisole. Select a shirt that is a little loose so that the camisole peaks out. Then, pair this with your favorite knee-length black skirt. Add a pair of closed-toe heels for a fabulous look for most offices.

You may also want to wear an oversized pink shirt and black shorts to the gym. This outfit has enough sophistication that you can easily wear it to run errands before or after your workout. Wearing a crop-top underneath allows you to take the shirt off if you get too warm.

Beige oversized shirt

When I tend to get too emotional or think I may be heading into a situation that could invoke those emotions, I love to wear an oversized beige shirt with gray bottoms as it helps to settle me down. On the other hand, if I need to add excitement, I love to wear my oversized beige shirt with orange trousers.

A button-up beige oversize shirt is a fantastic option to wear with gray dress trousers. Choose an option tailored so that the pants stay close to your body. I love this look with black shoes and accessories.

If you are going to an interview or a meeting where you want to get noticed, wear an oversized beige shirt with an orange skirt. Then, choose a blue-green handbag and accessories. This would also be a perfect outfit for dinner at a casual restaurant. I love to wear this look with navy shoes that match the occasion where I am going.

Oversized linen shirt

Linen is a fantastic choice when you want to add an air of sophistication to your outfit. You can opt to create a linen outfit by wearing a shirt with a pair of linen pants. You may want to create a monochromatic outfit by staying in the same color family. But make sure that they are far enough apart that the colors do not clash.

One look that is extremely easy to put together is a black-and-white outfit. Choose a white linen oversized shirt and pair it with black linen dress trousers. 

For a semi-formal occasion, choose a white handbag and accessories or for a more casual look, opt for colorful accessories. A red necklace and matching shoes are a great way to add a pop of color.

A linen shirt also makes a great swimsuit coverup. Wear a patterned option over your solid-colored swimwear to give it a splash of color. A black swimsuit with a yellow-and-gray oversized linen shirt is a fantastic option. 

You can choose to tie a large scarf around your waist as a skirt if you want. Then, put on your favorite flat sandals. Ones with a bit of sparkle are a great choice if you want to keep the sophisticated vibe going.

Oversized cotton shirt

Arguably the most prevalent choice in oversized shirts is a cotton option. You can style it in so many ways that you will find yourself reaching for it often. Wearing it open up the front, like a deconstructed blazer, is a fantastic choice.

Consider wearing a dark-colored cotton shirt over your favorite graphic t-shirt. Then, wear your skinny gray jeans. This is a fabulous look to wear with sneakers when running errands.

You may also want to wear it with your jodhpurs. In that case, you can button the shirt up and tuck the front in while leaving the back untucked. Then, wear your black riding boots. You may even want to wear an equestrian riding hat to keep the boyish vibe.

Animal print oversized shirt

An animal-print oversized shirt is a fun option to wear on a casual date. While your mind might instantly go to leopard print, you will also want to consider other options, like giraffe, cow, or tiger prints. Unless you are very young, avoid patterns that do not resemble the animal’s coat.

An animal-print oversized shirt is a terrific option for wearing open over black leggings. Then, wear your black shoes and your black accessories. Slip-on a cowl-neck shirt under the oversized shirt if the weather is chilly.

An animal-print shirt is also a fantastic option to wear with a skirt that comes to about your knees. You do not want one longer than that, as your outfit needs to stay casual. Then, opt to wear it with your flat sandals. You can carry a crossbody bag to add a pop of color. Purple, true red, persimmon, and royal blue are all great choices.

I have given you a lot of outfit ideas in this chapter, but sometimes, too much detail can be confusing. In the next chapter, we will look at many general ideas of what to pair with oversized shirts. Therefore, make sure that you keep reading.

Oversized shirts outfit ideas & combinations

While you started to get a hint of how versatile oversized shirts were in the last chapter, I hope you gain an even better understanding of why you need several oversized shirts in your closet. The possible ways to wear them are almost endless. Instead of focusing on details in this chapter, we will focus on overall styling.

There are not many items of clothing you can wear as a dress or with your favorite jeans. They are also an excellent option for wearing with dress trousers. 

The possibilities are almost limitless when you start considering the number of colors and designs, from t-shirts to tailored options available in oversized shirts. 

These shirts easily move from spring to winter, so you can wear them all year long, extending your clothing budget.

You saw this in the last chapter, so this time we are going to focus on ways you can put different outfits together.

Oversized shirt + blazer

An oversized shirt is perfect for wearing with many types of blazers. You can wear one with lots of design details to the office with high heels, but my favorite way is to wear them with a deconstructed blazer. They go perfectly with your dress shoes, but I also love wearing them with my sneakers for a more casual look. 

As I mentioned, they are ideal for wearing with a skirt to the office, but you can also wear them with your dress trousers. You can easily create monochromatic outfits or have fun combining different colors, like creating outfits using split complementary colors.

Oversized shirt + shorts

An oversized cotton shirt is a fabulous choice for wearing to the gym with a pair of athletic shorts and your favorite cross-trainers. On the other hand, pair them with biking shorts for a fabulous outfit to wear on a family bike ride. When it is time for your run, they look fantastic with your favorite running shorts and shoes.

Woman waiting outdoors dreadlocks

The only thing you need to be cautious of is that they do not get caught up in exercise machinery. If you plan on lifting weights, using the rowing machine, or using some other type of equipment, consider wearing a muscle shirt under your oversized shirt and taking off the oversized shirt when using the equipment.

Oversized shirt + skirt

You can wear an oversized shirt with many types of skirts. You can wear them with your favorite mini skirt and add some bling jewelry for a night out on the town. You can also wear them with a knee-length skirt to a fabulous casual dinner. 

When the beach is calling your name, wear your oversized shirt with a scarf or wraparound skirt. The type of shoes or boots you wear depends on where you are going, as oversized shirts look super with flat sandals, boots, and kitten-and-high heels. 

You can also use jewelry to dress them up or down, and carrying the right handbag style helps polish off the look.

Oversized shirt + leggings

Oversized shirts look great with your leggings. In the winter, you may consider wearing an oversized sweater with your leggings. As I have already discussed, your leggings and shirt will look fabulous with a blazer when the weather cannot make up its mind what it wants to do. 

You can easily create a monochromatic outfit by choosing a shirt and leggings that are the same color or mix-and-match different colors. One of my favorite ways to wear an oversized shirt and leggings is to choose a pair that ends about my ankles, then wear them with colorful shoes. Then, I carry the same color in a crossbody bag.

Oversized shirt + jeans

Skinny jeans are perfect for wearing with your oversized shirt. You can opt to wear them with your sneakers or your flats. Give your outfit a 1980s flair by wearing them with a pair of platform shoes. They are a great option to wear with Doc Martens to create a grunge look. 

You can wear any color of jeans, depending on the color of the oversized shirt. Generally, excluding black jeans, the darker the jeans, the easier it is to create a semi-formal look. Alternatively, light-colored jeans are ideal for casual wear. As I mentioned in the last chapter, I especially love the look of pink with gray jeans.

Oversized shirt + leather jacket

An oversized t-shirt is perfect for wearing with a motorcycle-style leather jacket. Then, wear them with your Doc Martens and your distressed jeans. Alternatively, they look great with your cargo pants, especially if you add some chains to your waist. 

In this case, you may want to choose a shirt with your favorite grunge band on it or a funny saying. On the other hand, an oversized shirt and a nice leather jacket are perfect for pairing with a pencil skirt and your ankle boots. In that case, you may want to consider a shirt made from linen that buttons up the front.

Oversized shirt + swimwear

An oversized shirt makes an ideal beach coverup. You may want to consider a shirt that buttons partway up the front because it will let your swimsuit top peek out from underneath. As I mentioned earlier, another terrific choice is to wear it with a silk scarf skirt. 

Wrap a large rectangular scarf behind you and tie it on one side. A third alternative is to wear the shirt to the beach with shorts. Choose an option that will dry quickly. You will stay cooler at the beach if you choose a light-colored shirt.

Oversized shirt + jodhpurs

If you love English riding, an oversized shirt and your jodhpurs may be an ideal outfit. Choose a white one and pair it with brown or black jodhpurs to create a classical look. Tuck in your shirt. This option is terrific when riding as it will keep you covered. 

Choosing riding boots with at least a 1.5-inch heel so your foot does not get hung in the stirrup. You will want to wear a great sports bra underneath to keep looking polished while posting. A riding helmet to keep your head safe in case of an accident is always a great idea.

Oversized shirt + dress trousers

When you must settle down and get work done, consider wearing an oversized shirt with your dress trousers. They will look great with your high heels. This can also be a fantastic outfit to wear when going to a casual event because dress trousers are tailored to stay close to your body.

Two women posing looking camera striped shirts

While you may want to keep the jewelry simpler when heading to work, you can add some brightly colored jewelry when wearing this look casually. Just make sure not to overdo it, or your outfit will start looking too busy. Your sneakers are a fantastic choice when you are wearing the outfit casually.

Oversized shirt + khakis

An oversized striped shirt is a fantastic option to wear with your khakis and tennis shoes. You can choose to wear a button-up option over a crop top and just button the middle button. Then, add a belt to your khakis. 

This is an excellent choice if you want to look thinner because thin vertical stripes make you appear as if your sides are not as far apart. Vertical stripes are also a fantastic choice if you want to look taller. 

Choosing an option with horizontal stripes across your chest is a great way to draw attention to this part of your body if it is a strong suit. If you want to look a little bigger, consider a shirt with overall horizontal stripes.

Oversized shirt + capris

Capris are a fantastic choice to wear with an oversized shirt. Choosing a two-piece set with a pattern makes a great option as you can be sure they match. Then, wear them with your favorite flat sandal or sneakers. You can also wear an oversized patterned shirt with neutral-colored capris. 

This is a superb choice for many office environments when paired with your closed-toe kitten heels. Options made from terry cloth are fantastic to wear to the beach with your flat sandals. I especially love this look when the capris are made of denim for wearing on a weekend country getaway or to the farmers market.

Oversized shirt + white jeans

Plaid oversized shirts look perfect with white jeans. It is easy to give this look a country vibe by wearing them with your western cowboy boots. Opting for a shirt with a lot of white in the plaid and pairing it with matching white jeans can be a terrific option. 

Alternatively, you can take an oversized houndstooth shirt and wear it open over a white button-up shirt to create a vintage-looking outfit. In that case, moccasins are ideal footwear. 

You can also wear the oversized shirt as a blazer, wrap a scarf around your neck, and put on your white jeans to give your outfit a Mexican flair. In that case, you may want to consider wearing a small sombrero.

I hope you now have some new ideas for oversized shirt outfits that you want to try. Before you start shopping, read the next chapter. It gives you many specific tips about styling oversized shirts. Then, when your new clothes arrive or are in the store while trying them on, you will know precisely how they should look.

Tips for styling oversized shirts

Now that you are ready to choose several oversized shirts let’s look at how you should style them. There are many beautiful possibilities of what you can wear with oversized shirts, including capris, jeans, and skirts. However, the final touches that make an outfit from OK to extraordinary lie in understanding how to style them to make them look gorgeous.

Have you ever loved an outfit in a store and gotten home to discover that you have no idea where or how to wear it? After reading this post, I am sure that will not be true of oversized shirts that you add to your wardrobe. 

Yet, you may need some help adding the final touches that turn an outfit from its clean so that I will wear it to this is my favorite outfit, and I want to wear it as often as possible.

Here is some guidance that you may need to style your oversized shirt:

Roll up the sleeves of your oversized shirt

If the sleeves seem a little big on you, roll them up a turn or two. This gives the shirt a more casual flair, so be sure to choose the right opportunities to do this. Shirts paired with most capris, jeans, cargo pants, and shorts will look great with their sleeves rolled up a turn or two. 

Woman looking side outdoors shirt
Source: Valerie Elash on Unsplash

I would not roll them up if I were wearing an oversized shirt as a dress to a semi-formal affair or wearing one with a belt to a club. You may also want to consider what the wrong side of the fabric looks like before rolling up the sleeves.

Belt your oversized shirt if it’s too loose

If you dislike the shirt because it seems too loose, then add a belt. You can choose any belt, but often a simple one is best. You should choose a belt that compliments the primary color in your outfit. 

Black belts are an ideal choice if you wear dark colors, but if you wear vibrant colors or browns, then choose a brown belt. If you want your outfit to camouflage your stomach, consider pulling some fabric up and letting it fall over the belt.

Choose the Right Size

Especially if you are petite or thin, you must select the right shirt. One that comes about mid-thigh is perfect. You also do not want it to be so wide that it looks like you are a stick figure with an oversized shirt wrapped around you. 

Choose to wear the shirt with bottoms that balance out your look. Be careful that the top does not overpower your bottom half or the other way around. Be sure that you are showing a little skin. Wearing distressed jeans is one option, but you could leave the top buttons unbuttoned or roll up the sleeves.

Tuck it in to keep your shape

You can find many options in oversized shirts that are ideal for tucking in so that your figure shows. If you want to keep the shirt from appearing puffy, put your pants or bottoms on, but leave them unbuttoned. Then, pull the shirt down until it is taut. 

Pinch the side seams on both sides to gather excess fabric. Then, fold the part that you have collected towards your backside. Now, fasten your bottoms to hold the folds in place. If you are wearing bottoms with an elastic waistband, use a belt pulled tightly around your middle to hold the folds in place.

Choose the correct shoes

You can wear various shoes with oversized shirts, but it is essential to choose the right ones. Flat sandals without much detailing are usually best if you are going to the beach and using your oversized shirt as a coverup. 

Alternatively, if you are going out to a casual dinner or event, then kitten heels are ideal because you can easily walk in them. You can choose between sandals and closed-toe options. 

You may also want to consider your sneakers and canvas slip-on shoes. If you are going to the office, think about the dress code, but you can easily wear them with high heels.

Knot your oversized shirt

Another terrific way to wear your oversized shirt is to knot it, and you can choose between various techniques. One of the simplest is to knot it in the front. Fold up the fabric in the back. Pull the leftover fabric to the front and twist it into a spiral. Wrap it around until it forms a ball. 

Finish by pulling the end through the ball. After you gather the fabric in the back, you can keep rolling it. Then, form a spiral in the front and tuck it under the rolled part. This is a fantastic look to wear with a bikini if you want part of it to show while you have your shirt on.

Consider the occasion before selecting your oversized shirt

Manufacturers make oversized shirts from various fabrics. Therefore, you should consider which material best meets your needs. If you are going to wear it to the office or a weekend away, consider those made from linen as they look sophisticated. 

If you are going to wear it while lounging at home or to a very casual event, then a t-shirt may be best. Those made from cotton are ideal for wearing to most casual events with your jeans or khakis. You may even find terry cloth options terrific for the beach because they absorb water exceptionally well.

Select the right bottoms

As you have seen in the previous chapter, you can wear oversized shirts with many different bottoms or no bottom at all. Therefore, it is vital to consider where you are wearing the outfit before making a final decision. 

Two women hug smile red white clothes

Jeans, cargo pants, khakis, and most capris are perfect for wearing to casual events. You may want to wear skirts that come at least to your knees to work with your oversized shirt, while those that come above your knees are ideal for casual events. 

In addition, think about wearing the oversized shirt as a belted dress to work. Bright colors are ideal for casual events, while neutrals and darker colors are an excellent choice for work.

Wear your oversized shirt as a beach coverup

There are an incredible number of ways that you can wear an oversized shirt as a beach coverup. You can knot the shirt in the front or back and wear it with your swimwear bottoms to help block some of the sun’s harmful rays from getting to your shoulders and back. 

They are perfect for wearing with quick-drying shorts. You may want to wear it with a belt and put it over your swimwear. Alternatively, you can choose only to button a few buttons and let your bikini peek through. Make sure that the option you select works with the color of your swimwear.

Think about color combinations

Oversized shirts are an excellent option for creating monochromatic outfits. Alternatively, they look great when worn with neutrals or the right colors. Consider choosing the colors that you wear based on the color wheel. Start with the shirt’s primary color and go straight across the color wheel to find its opposite color. 

Then, move one space to the right or left to find the split complementary color. Choosing this color for your bottoms is an excellent choice. Then, add a touch of the other color to your outfit. Remember that dark and neutral colors are best for work and formal occasions, while brighter colors are ideal for casual events.

In the next part, I will allow you to ask questions, and I will do my best to answer them. I also have two small favors to ask of you, so be sure to keep reading.


Now that wearing oversized shirts is no longer a scary proposition because of your knowledge about the different styles and how to pair them with items in your wardrobe, have fun shopping for them.

Before you go, I want to invite you to leave any questions you have about oversized shirts. I will do my best to answer them.

Shopping is always more fun with a friend, so share this post with one or more so you can all know how to pick out the best-oversized shirts.

You may want to let one of them do the driving so that you can read our other informative posts. Then, you will be prepared to pick out other clothing to wear with your oversized shirts.

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