How to dress over 50 & overweight – Tips & Outfit Ideas

How to dress over 50 & overweight - faverie

Older women often have experienced a lifetime of living. They have spent hours caring for children and elderly loved ones. These women have often worked full-time jobs while keeping their children involved in all sorts of positive activities. 

They have often eaten the wrong foods, even when they knew better, because it was what was available while cheering for their families at sporting events and youth programs. Many must confess that they did their share of stress eating while waiting for a teen to come home at night or a phone call from a college student.

Now that their families can better care for themselves because of their love and dedication, many realize they do not know how to dress over 50 and overweight.

Ladies, don’t worry. I have lots of helpful advice and some outfit ideas in this post.

How to dress over 50 and overweight

Older women are often so full of wisdom they have gained through a lifetime of living. As they sat in bleachers eating concession stand food while cheering their children’s accomplishments and mending broken hearts, instead of taking the time to exercise themselves, the pounds slowly packed on.

Additionally, many have spent countless hours making costumes, planning birthday parties, and other activities in the wee hours of the morning instead of getting enough rest, which made it even easier to gain weight. Sometimes, they have eaten the leftovers while letting others have the most nourishing foods because they knew the grocery budget would only go so far.

Now, those women have become proud older adults, and as the children leave home, they can finally take time to care for themselves. At the same time, they plan family get-togethers and dinners with their grandchildren and others so they can pour their wisdom into them and hopefully do not have to learn the hard way. To look like someone the younger generation wants to take advice from, you need to look your best.

In this chapter, we will examine what women over 50 should wear, especially if all those wisdom-earning experiences have left them with a few extra curves.

Here are some general guidelines you might want to consider:

Ensure your clothes fit well

As you age, your body naturally changes shape, even if you have not gained or lost any weight. Therefore, you must take a good look at your clothes. They will not look right if they are too tight or too loose. 

These clothes need to be passed on to others, especially if you have spent more on quality clothing as your salary grows. Someone else will likely love wearing them, and you will be delighted that you can bless someone.

Keep it simple

One of the joys in growing older for most women is that you realize that it takes far less to make you happy. All those material things you worked so hard to obtain no longer seem to matter as much. While this can apply to your overall life, it is also true of your wardrobe.

Group women smiling holding hands

Reducing the size of your overall wardrobe can be mentally freeing, and you do not need to wear complicated clothing choices. Instead, opt for simple outfits in a few basic colors. As with clothing that didn’t fit, blessing someone else with these items can boost your and their mental health.

Wear the right colors

Many women find that their skin tone changes as they age. Therefore, it is also time to reevaluate what colors look best on you. In my opinion, one of the best ways to keep your wardrobe simple is to focus on neutral colors. 

Start by ensuring you have the basics covered in blacks, blues, whites, and grays. Then, add a favorite color or two. Go with split complementary colors for your accessories, and you will have a beautiful wardrobe that will make you look fabulous. 

The great news is that everything will match, so you can easily wear what is clean if a fun activity comes up and you do not want to do laundry.

Layer your outfits

Layering outfits is an excellent idea as it lets you easily adjust throughout the day. You can endure those hot flashes better when you take off layers and put them back on later. You will also love being able to put on extra layers if you must sit under a cool air register or take them off if you are sitting where the heat from the furnace is blowing on you. 

When creating layers, look for options that allow you to create vertical lines, as they will make you look taller. Remember that wearing dark layers on the outside will make you look smaller.

Focus on your strengths and enhance them

Even though you have a few extra curves, your body still has strong and weaker points. You will want to draw attention to your strong points while deemphasizing your weaker ones. Tucking the front of your shirt in, called a French tuck, will make your legs look longer. 

This keeps the hem of your shirt from hitting the widest part of your body, so you instantly look thinner. If your upper body is your strong suit, add a pop of color near your neck so that the viewer’s attention is naturally drawn upward. A V-neck shirt with a statement necklace can be a fantastic option.

Make sure your waistline is well defined

Older women with a few extra curves need to be sure to wear outfits with well-defined waist. There are several ways that you can define your waist. While belts are a great option, if you do not like the pressure they sometimes put on your stomach, there are many other choices. 

Consider an outfit that has a unique pattern near the waist. Tops with color blocks near the waist can be another fantastic choice. Likewise, consider pants that have a different color around their upper part than the lower leg.

Choose the right shoes

Women, when you reach 50, you have walked about 54,750,000 steps or about 22,465 miles as you met the demands of your job and family. Therefore, it is very common for women, especially those who are overweight, to start having problems with their hips, knees, and feet. 

Opting for shoes with good cushioning can help you feel more comfortable walking. Think about choosing options with a wide toe box, especially if you have corns, arthritis, or other foot issues. Shoes that have good traction on the bottom may make walking easier.

Select the correct handbags

As a curvy woman, consider larger handbags as smaller options will make you appear even bigger. Therefore, make sure you opt for larger handbags. When buying new options, look for ones with longer than average handles based on the type of purse because you will look better carrying them. 

Carrying bright-colored handbags is the perfect option for adding a pop of color to your outfit, especially monochromatic ones. Consider adding a statement bag to your collection that showcases your personality.

Select the right prints

If you want to look thinner, you may be tempted to reach for vertical stripes often. While they can be a good option when choosing clothes that hang a little ways from your body, consider lines that are made up of tiny dots or patterns because if the clothing item is too tight, then the lines turn squiggly and draw attention to your weight. 

When choosing patterns, opt for smaller designs or options that appear to break into smaller pieces when a viewer gets closer. As I mentioned earlier, color blocking can be your friend if the brighter colors are in areas that are your strong suit.

Pick the right sleeve style

Tops with ¾-length sleeves are usually the most flattering. These sleeves will help camouflage the upper part of your arm, which is often one of the areas where extra weight is easiest to spot. For most women, these sleeves end at the smallest part of your lower arm. 

If you are afraid they will be too warm, consider options you can push up a little. Kimono and bell sleeves can be other terrific options. Look for options that hang down a bit as they naturally create verticle lines, making you look taller and thinner.

What should you not wear if you are overweight in your fifties?

Women who have already celebrated their 50th trip around the sun and packed on a few extra pounds through memory-making experiences will want to avoid clothes that are too baggy or big. While you may be tempted to wear them thinking they will make you look smaller, you will actually look bigger.

Avoid round necklines

A round neckline will make you look even rounder, so you will want to avoid wearing them. Instead, opt for a V-neckline if you want to appear even taller. A sweetheart neckline can be another great option as they are almost universally flattering.

Couple man woman taking selfie park

If you fall in love with a top with a round neckline, wear a pin or something on the shoulder, as it will help pull the viewer’s attention upward and away from the neckline. If you have some basic sewing skills, you can also turn a round neckline into a square one, which will look much better on you.

Don’t wear outfits that are too loose or too tight

You may be tempted to wear outfits that are too loose on you because you mistakenly believe that they will help camouflage your weight. The opposite is also true. You may be tempted to wear clothes that are too tight, especially if your weight gain seemingly came on overnight. 

Wearing clothes that are the right size will help you look your best. If you are quickly changing sizes, consider thrift store shopping as you can often find options that are just right for you, and some may be new with the tags still on them.

Do not wear horizontal striped tops

Most older women who are overweight already know that they should not wear horizontal stripes. While vertical stripes can be a great alternative, opt for choices that have thicker stripes. 

Thin stripes, like pinstripes, can also give the illusion that you are bigger. You can also make check patterns work for you if you choose those with wide checks. Steer clear of tiny checks, as they will make you look even bigger.

What makeup looks best on overweight women over 50?

Since older women sometimes lose part of their youthful glow, you must recreate that look when putting on your makeup. That starts with a good skincare routine of exfoliating regularly and using a weightless moisturizer. Select options with lots of nutrients in them.

You cannot hide wrinkles, so it is pointless to try. The chances are that you will end up drawing more attention to them. Apply a sheer foundation to even out your skin tones. Then, apply a creamy concealer. 

When choosing concealers and foundations, go one or two shades warmer than your skin tone because it will stop you from looking washed out. Pay special attention to your eyes if you suffer from dark circles under them. They will look less noticeable if you apply concealer to the inner corners to help balance the look, especially if you have laugh lines.

To achieve a youthful glow, put your blush on the outside of the cheekbone and blend inward. This will help pull attention upward and make it less likely to look like gravity has affected you.

You want to play up your eyes to make them look more youthful. Start by curling your lashes and using mascara. Avoid any mascara that makes your lashes clump. If you want to wear eyeshadow, it should be darker on the outside edges and lighter as you move towards your nose.

When working on your lips, your goal should be to make them look symmetrical. Use a lip pencil and draw four lines, each pointing towards the cupid’s brow. Then, smooth the lines together before finishing with a slight glossy lipstick, but never use one that is too heavy.

What hairstyles are the most flattering for middle-aged ladies?

Many styles look lovely on middle-aged women if their hair still has a lot of volume. The problem for many women is that their hair becomes straighter as they age, and straight hair will make you look older. If this is an issue for you, consider short hairstyles for women that will add volume back to your hair.

If you are older and have neglected to spend time in the gym, avoid short haircuts with blunt ends. They will make your face look rounder, making you look even heavier. Messy buns and top knots can make you look taller, helping to elongate your face.

Another fantastic option is to wear hairstyles with a center part. Line up the part with the arch of your eyebrow. Then, add some extra height by teasing your hair. Select the right hairspray to hold it in place.

If your hair is curly, work with it so the curls go higher in the air instead of wider. This will help you look taller, and your face will look thinner. If the curls are wider, they can make you appear even broader.

If you wear longer hairstyles, be sure to keep your hair healthy. Hair naturally becomes more brittle as you age. Therefore, you need to be using a nourishing shampoo and conditioner. If you are going to wear hairstyles that require using hot irons, curlers, and other tools, think about using a leave-in conditioner.

How to accessorize your outfits?

When adding accessories to your outfit, create a focal point. Never wear bold necklaces and earrings together because you will end up looking like the Christmas trees you used to have when your offspring were little. Be careful not to mix too many colors as they will clash.

When choosing accessories, first think about what part of your body is your strongest suit as there are many options, including scarves, handbags, bracelets, necklaces, and earrings. The items that you choose should fit the style of clothing you are wearing. 

If you are going to a more formal event, choose jewelry that stays further away from your body than if you are going to a casual one. For example, your dangle diamond earrings are perfect for a formal event, while your diamond stud earrings are perfect for a casual one.

Think where you want to direct the viewer’s eye. If you are going to direct it upward, wearing a scarf around your neck or a pin on your shoulder can be a great choice. Alternatively, a colorful scarf around your waist or a pretty anklet and toe ring will look terrific if you want to direct it towards your legs.

Choose the color of your jewelry carefully. Anything too bold can make your skin look washed out if it has gotten lighter as you have gotten older. When selecting the color of your jewelry, think about using a color that is a split complementary to the colors in your outfit when wearing a casual one. 

Woman posing looking camera jewelry

If you are going to a more formal event, opt for more sparkly jewelry than a casual one. It is far easier to wear too many accessories than not enough, so be sure to limit your choices.

What colors look best on oversized ladies based on their body types?

Generally, you will want to wear lighter colors where your body looks its best and wear darker colors where you want to deemphasize your body’s shape. Pay special attention to where you switch colors, as particular emphasis will be drawn to this area. You will also want to avoid bold colors if your skin is starting to lose some of its pigment.

If you have a rectangle or square body, wear lighter colors on the top and bottom while wearing black and neutral colors near your waist. This will help to break up your body’s silhouette where its straight lines are not as noticeable.

Alternatively, if your body is a triangle or pear, wear light colors on the top and dark colors on the bottom. You may even want to wear a top with a different color across your shapely bust to emphasize it.

Wear lighter colors on the top or bottom if you have a spoon-shaped body. You should stick to darker colors around your thicker midsection.

Apple or inverted triangle women look super when they wear lighter colors on the bottom as their legs are their strong suit. Since their widest part is around the middle, you should wear dark colors there.

Brightly colored off-the-shoulder tops look fantastic on women with diamond-shaped bodies. Avoid wearing bright colors near your waistline or on your upper legs. Since your lower legs are usually shapely, wearing bright colors there can be a fantastic choice.

In the next chapter, I will give you some advice on what to wear depending on where you are going. Therefore, you will want to keep reading as I will discuss types of pants, dresses, shoes, tops, and other clothing items to wear as a mature overweight woman.

How to dress over fifty

Many women who have had over 50 years of memory-making experience feel that they can no longer look beautiful. That is sad because the truth is that you can look beautiful regardless of your age. It depends on your outlook on life, so keep it positive. Embracing these looks will help you look gorgeous on the outside.

By the time most women turn 50, they are done with the drama that they helped create in many cases through inexperience. The busy days of raising children are over or nearly so, and you may now have a little extra to spend on yourself.

Part of that comes from the inner glow radiating from your soul. The other part comes from embracing your body regardless of its weight through how you dress.

Consider these fabulous ideas as you move through each phase of your life.

Formal wear

There are many types of dresses that women 50 and over can wear for a formal occasion. If your upper body is your strong suit, consider options with wide straps and a fitted bodice. Those flaring out a little, like an A-line skirt, are great options.

Options with a side split are easier to walk in, and their long vertical line can help you look taller if your legs are your strong suit. Sticking with dark neutrals can help you look thinner.

You may also want to consider formal cocktail dresses. When choosing an option, consider the ones that have more bling on the part of your body that is your strong suit, as it will help capture the viewer’s attention. Check the length or have it hemmed to end at the thinnest part of your lower leg.

You need to choose an excellent updo hairstyle for a formal event. Focusing on putting your hair on the top of your head, as in a bun, can be a great choice as it will help add some height to your frame. Then, you can opt to wear a diamond or other hair accessories around it.

Casual wear

Pastels are an excellent option for daytime casual wear. As I discussed earlier, the best option is to wear a lighter color where your body is the strongest and go with a dark color where it is weakest.

Woman posing black skirt

High-waisted jeans are a great choice because it is easy to create a definite waist with them, and the look will elongate your legs. While not valid for every woman, dark-washed jeans usually make you look slightly slimmer. Bootcut jeans will usually enhance your looks without being too tight.

When choosing casual, be sure to consider the different types of shoes that are available. Those with plenty of padding and a deep heel cup are usually more supportive. Ensure that there is enough room in the toe box so that your toes can move freely.

Office wear

Women who have made more than 50 trips around the sun are most comfortable in pants at work, and you can choose between many types of pants. Bootcut trousers can be a fantastic choice as they usually have enough stretch to move as you move throughout the day. Cropped pants can be an excellent choice if they do not make your legs look too short.

Party wear

An A-line cocktail dress can be a fantastic choice for a party, but it is certainly not the only type of dress that you may want to consider wearing to a party. Options with an asymmetrical hemline can be an outstanding choice, especially if your legs look fabulous. Halter dresses with wide straps can also be great if the top fits you correctly.

When heading to a party, consider the types of shoes complementing your outfit. While more formal parties require high-heel shoes, you can wear flats or kitten heels to many parties. 

Depending on the outfit chosen, ballet flats can be a great option if you are likely to be dancing the night away. Pumps can also be a great choice, especially if they have a little bling on them.


You can choose between several styles of swimsuits when heading to the beach. One-piece suits can be a fabulous choice, especially those with ruching on the side. You may also want to consider tankinis. Ruffles can help hide the weak parts of your body, and swim dresses and skirts often help your upper body look longer.

If you are uncomfortable wearing shorts in public, consider a pair of capri pants. Make sure you choose options ending at the thinnest part of your leg. Then, wear it with your swimsuit top or a tank top. Those with wide straps across the shoulders provide the most support.

Regardless of what you decide to wear, choose a hat with a wide brim. Sun hats are a fantastic option, but you could also go with a bucket, Panama, boater, or a Boonie hat. You can choose between many types of shoes, but do not try to wear your high heels. You will probably fall, and broken bones do not mend as fast when you are older.

Semi-formal wear

Many types of dresses are great for semi-formal events. Your hemline should end a little below your knees. You may also want to think about a button-down shirt and a skirt. When selecting from the many types of skirts, choose those that stay a little away from your body for a semi-formal event. Maxi, asymmetrical, A-line, and flared can be fantastic choices.

When selecting the type of jewelry you will wear, consider the venue. While you can go with more colorful options, you can also opt for classic diamonds, pearls, gold, or silver jewelry. Just be sure not to overdo it. Wearing one statement piece may be all that you need.

Likewise, when choosing your shoes, thinking about the venue can help. You can opt for high heels, but your dressy sandals or kitten heels will also work.

Everyday wear

I have already discussed the best style of jeans for women over 50. Let’s focus our attention on the types of tops to wear. Select options that feel soft against your skin. Those made from natural fabrics or special built-in technology will wick moisture away from your body, so you stay cooler. 

A monochromatic outfit often has a slimming effect. Consider tops with vertical lines that fit you properly. The lines can be printed on the fabric, formed by a row of buttons, or in the sleeve and neck design.

Women over 50 can also wear many types of coats. If you are bigger on the top, skip options with a belt and those with a breast pocket. If you live in a climate that gets cold or tend to be cold-natured, think about coats with contoured down patterns. 

Alternatively, coats with a cinched waist can help break up your body’s silhouette and look fabulous on you if your waist is a strong point or you have a square or rectangular body build.

I hope you have enjoyed learning how to dress for different occasions. In the next chapter, I will offer you some fashion tips if the memory-making experiences have added a few extra pounds to your frame. Therefore, I encourage you to keep reading.

How to dress if overweight

If your responsibilities at work and home have left you little time to exercise, you may not be the same weight you were when you graduated high school. Furthermore, you may have found it stressful to take care of your job, home, and family all at the same time and gave into the temptation to stress eat.

Some women who are 50 and over find that their metabolism slows down or they have other medical concerns making it impossible to maintain a healthy weight. If that is the case, following some tips can help.

As you look back on life, you may need to give yourself a lot of grace and a big pat on the back. Regardless of what life throws your way, you are a survivor, and you deserve a round of applause regardless of your weight. 

If you have not already done so, accept the woman staring back at you when you look in the mirror. It can be challenging to accept yourself as you are, but it is a vital step toward developing or keeping healthy self-esteem.

It is vital that you never stop trying to create a better you, regardless of your age. Dressing your best daily can be a great start, especially if you are overweight.

Create a focal point

If you have looked at a painting and started feeling anxious, it may be because your eyes had no place to rest. When you are putting together outfits, make sure that the viewer’s eyes come to rest on your strongest suit. 

Woman eating restaurant mustard top

You can do this using several different techniques, but you should choose only one for each outfit. For example, you can wear color only in that area while dressing in neutrals for the rest of your outfit. 

You can also do it by using a flashy accessory in that area. Alternatively, you can leave an area uncovered, such as with a one-shouldered or cold-shouldered top, if your shoulders look marvelous.

In many cases, you will want to draw the viewer’s attention up to your face. Then, the way that you apply your makeup becomes crucial.

Choose undergarments that offer support

Women aged 50 and over may find that gravity has affected their bodies. Therefore, shapewear can be your best friend because it helps keep body parts where they belong. Likewise, if you have a big bust, a sports bra with wide straps can be a fantastic option if it is the right size. 

It is wise to measure your body before buying new undergarments because you may find those that fit a few years ago no longer fit properly. You will feel fabulous when you wear the right size as they support your body correctly.

Especially when ordering online, be aware that companies do not all use the same size chart. Therefore, make sure you locate a size chart for that company before placing an order because some undergarments cannot be returned.

Select quality over quantity

It may be tempting to go with cheaper fabrics if you have not yet embraced your body’s size, but that would be a horrible mistake. Ensure that you are budgeting enough for clothing to buy quality clothing. 

If that is difficult right now, consider creating a minimalistic wardrobe. This allows you to mix and match many pieces to create different looks.

When choosing items to add, consider those that are classics. For example, midi dresses, button-down blouses, bootcut pants, pencil skirts, A-line dresses, and structured cardigans are never going away. Investing in these pieces helps your budget go further. Stick with neutral colors and add one or two seasonal colors.

If money is tight, consider thrift store shopping. You can often find clothes there that still have the price tag on them. While I will have more to say in a moment, buy clothes that fit you properly because they will help you look smaller.

Pick out neutral colors that complement your skin tone

Many factors can change your skin tones as you age, including long-term sun exposure, medications, and skin conditions. Try this experiment. Hold a piece of white typing paper up to your face and look in a mirror. 

If your skin tone looks yellow, green, or light brown, you have a warm skin tone, but if it looks pink or blue, you have a cool skin tone. You have a neutral skin tone if your skin appears gray or ashen. 

If your skin tone is warm, you will look great in taupe, cappuccino, cream, and mushroom gray, but if your skin tone is cool, wear cool gray, bright white, and navy. Finally, opt for off-whites, coffee, mid-range grays, and black if you have a neutral skin tone.

As I mentioned earlier, wearing neutrals on your weakest body parts is a great way to make them look smaller. Therefore, you can wear them on top or bottom so that your biggest body parts tend to appear smaller.

Embrace form-fitted clothes

You may be tempted to wear clothes that are too big for you because you think they will make you look smaller, but the truth is that they will make you look even larger. Likewise, I encourage you to clean out your closet and give away clothes that are too tight. 

Wearing them will also make you look bigger. Plus, they are very uncomfortable in most cases. In many cases, you may feel like you have spent a lifetime wearing clothes that were not your favorites. 

Therefore, now is the perfect time to wear form-fitted clothes. You will look fabulous in them, which is an instant boost to your self-esteem, and everyone can use the boost regardless of where they are in life.

One word of caution. When choosing button-up blouses, ensure that they are big enough to cover your stomach and that they will stay buttoned when you move. After all, you do not want people to see your luxurious undergarments. 

If you have a blouse that you love that is constantly gaping, grab some iron-on double-sided tape and attach it over the gap to ensure that it stays shut.

Accentuate your strong points with pastels

Pastels can be a fantastic choice for women who have accumulated a few pounds. As with neutrals, picking the right pastels based on your skin tone is essential to look your best. If you have dark skin tones, buttery yellows, lavenders, creams, and aquas look fabulous. 

Women with lighter skin tones look gorgeous in baby blues, powder blues, candy pinks, and pastel lilac. If you are in the middle, opt for mint greens, baby pinks, pastel grays, and peaches.

When wearing pastels, it is helpful to keep some generalizations in mind. You can easily wear too much pastel. So be sure to accessorize your outfit with a neutral or pieces from the same color family. 

All pastels look great together if you have clean lines between the different colors. If wearing more than one pastel simultaneously, avoid lace or outfits with cutaway designs because they will look too busy.

Make vertical lines your friend

Especially if you are shorter, clothing with vertical lines can be your best friend, but you should ensure that the lines stay straight if they are solid by choosing the right size of clothing. Otherwise, you will look like your clothing is binding on you, even if it is loose.

Woman plus size model posing dress

Instead of choosing outfits with solid vertical lines, consider options with images or broken vertical stripes, as it will be less noticeable when the lines move slightly while adjusting to your body’s silhouette. 

For example, you may want to wear a polka dot dress where the dots are in lines or choose one where the lines are formed by zigzags instead of straight.

Another trick to looking thinner is to buy clothes where the lines are further apart on the outside and closer together in the middle because it will help elongate your look.

Think about monochromatic outfits

Monochromatic outfits can be a fantastic choice, especially if you are a little fluffy. Again, it would help if you considered your skin tone when choosing colors. Put the lighter shade on your body’s strongest asset. 

Therefore, if you have warm skin tones, consider creating monochromatic outfits with red, peach, coral, orange, amber, gold, and yellow. You can also wear warmer shades of cool colors, like olive, moss, orchid, and violet-red. 

If you have cool skin tones, think about making monochromatic outfits from bright blues, emeralds, deep purples, lavender, ice blue, and pink. If you are in the middle, wear dusty pink, jade green, cornsilk yellow, and lagoon blue because frosty and muted shades look particularly fabulous on you.

Be particularly cautious if you decide to create a white monochromatic outfit. Often white has warm or cool undertones that may not be apparent when the item is hanging on the rack. Therefore, consider holding a piece of white paper against it to make the undertones more noticeable. You do not want to mix warm and cool whites together.

Accessorize the right waistline

Look at your body’s proportions before choosing pants or jeans. Choose a high-waisted garment if your stomach is one of your largest body parts. This will help elongate the look of your legs, and your stomach will look smaller. If your stomach is flatter, go with garments ending at your natural waist. 

Low-waisted clothes will help make your top half look longer. Regardless of your body’s shape, do not select clothes that change right at the thickest part of your waist. Additionally, avoid clothes that change colors at this point. Both will make you look bigger.

There are many ways that you can camouflage your stomach if it is a little too big. For example, wearing a belt right under your bust can be a great option. You may also want to consider peplum and asymmetrical tops and look for options like A-line outfits that flare out a little.

Opt for the right handbag

One accessory that you will need with almost any outfit is a handbag. As I discussed earlier, be sure that the straps suit your body’s proportions. A medium bag is ideal because it gives you room to carry all your essentials. Avoid carrying a small or extra-large handbag because it will make you look even bigger.

When choosing a handbag style, think about your body’s silhouette. If your body’s square or rectangular, a crossbody bag can be a fantastic choice because it will help to break up your body’s straight lines.

If the upper part of your body is your strong suit, choose a handbag ending above your natural waist. A purse that you carry from your shoulder or arm can be a great choice. Alternatively, if your lower body looks best, opt for a handbag with longer straps or one you carry in your hands.

I hope you have enjoyed these tips on what women who have stress ate, enjoyed many memory-making meals, or have medical issues that have left them overweight should wear. 

In the next chapter, I will discuss tips for dressing when you have made more than 50 trips around the sun. Therefore, make sure to keep reading.

Outfit ideas for overweight women over 50

If you have made more than 50 trips around the sun and eaten a few too many memory-making meals, you may wonder if it is possible to look beautiful. The answer is a resounding yes.

Mature women can look fabulous, even if they have medical problems, have packed on the pounds, have stress-eat, or just love food too much. While you will never look like you did in high school, you can still turn heads when you walk into a room. Consider these outfit suggestions.

Many women 50 or older have discovered a secret regardless of what they wear. Beauty starts from within. When you have a radiant glow, then you can enhance it with the proper skincare and makeup products. Then, you can further strengthen it by the way that you dress.

If you have trouble believing that these statements are factual, then put them to the test by wearing these outfits regularly. Start watching as you get compliments on how fabulous you look from family members, coworkers, clients, and even people on the street.

High-waisted jeans + asymmetrical top

High-waisted jeans are an ideal option for older women who carry a little extra weight in their stomach because it helps control the weight. An asymmetrical top is a great choice to wear with them because it does not form a solid horizontal line across the area that is often the widest on the woman’s body.

Woman smiling looking camera pastel top

Source: Madrona Rose on Unsplash

Consider a beautiful pastel asymmetrical top and dark-wash jeans if you want to slenderize your look. When choosing a top, look for one with a V-neck as it will help you to appear taller. You can easily opt for a cross-body bag to break up your body’s silhouette.

A-line skirt + button-up blouse

An A-line skirt is an excellent option for women who want to hide some of their curves because it flairs out a little. Pairing it with a button-up blouse is a good choice if you are headed out on a date or to work. 

Options made from silkier material will have a more formal appearance than those made from cotton or rougher textures, so consider where you are heading when choosing your blouse. 

You can wear this look with a variety of shoe styles. Your sneakers or flat sandals would be ideal for a casual dinner, but you could change the look by wearing them with your pumps or dress sandals.

Wrap dress + dressy sandals

A wrap dress gives an ultra-slimming effect because of its cut. Furthermore, the way it ties on the side helps detract the viewer’s attention if you have a larger midsection. Women with a square or rectangular body often look super in these dresses because they help define their waist. It is easy to dress up or down a wrap dress. 

Consider wearing it with your dressy sandals. Then, you can wear a diamond tennis bracelet and your diamond earrings. If you want a more casual vibe, wear it with a statement necklace and sneakers. Either way, a wrap dress looks great with a shoulder bag. Choose one with a bit of bling on it for a more formal event.

Cocktail dress + stilettos

A cocktail dress that comes a little below your knees is an excellent option for more formal occasions when you wear it with your high-heel stilettos. If your strong suit is your upper body, think about no-shoulder options. 

You may also want to consider choices with an asymmetrical hemline to help balance your look. Another great choice is lace options because it gives the viewer’s eyes something to look at. You may also want to consider choices with sleeves cut at a diagonal or added tulle sleeves as they will help camouflage your arms.

No-sleeve top + dress trousers + blazer

Dressing in layers is always a great choice for the office because you never know if it will be hot or cold. Consider wearing a no-sleeve top in a light pastel that matches well with your skin tone. 

Then, top it with a darker blazer from the same color family and wear a skirt that is about midway between the two. You can complete the look by selecting neutral-colored shoes and a gold or silver jewelry set. On the other hand, you could also go with a split complementary color for your shoes and jewelry.

Lace dress + pump shoes

A lace dress is a perfect option for a wedding or other special occasion. Opting for one that has a jacket will help to elongate your look. Alternatively, you may want to consider one that pouches out a little bit at the waistline as it will help camouflage your stomach. 

Your pumps are an ideal shoe choice to wear with your lace dress. The shinier they are, the more formal they will appear. If going to a wedding or other semi-formal or formal occasion, consider fixing your hair in an updo and wearing your diamond or gold jewelry. 

In that case, it is best to stick with a darker-colored lace dress. Consider wearing a pastel lace dress if the event is more laid back.

V-neck top + denim skirt

A V-neck top and a denim skirt is an ideal outfit to wear to a farmer’s market or a weekend away in the countryside. The V-neck on the top will help to elongate your looks, making it a particularly great choice for petite women. 

Choose a denim skirt that stays pretty close to your body, as it will look more casual than one with lots of flair. This is a great outfit to accessorize with a bandana. Consider tying it around your neck if you want to draw attention to your upper body. 

If your lower body is your stronger suit, choose a long, colorful one, tie it around your waist, and let the ends hang down.

Peplum top + pull-on knit pants

Pull-on knit pants with an elasticized waistband are a great option for lazy days and running errands around town because they move in many directions. Consider wearing it with a peplum top. The short section attached at the waistline will make your stomach look smaller. 

You can choose between a solid-colored top or one with a pattern but avoid any whose design is too big. If the weather is cooler, think about wearing this outfit with a leather coat that comes down about mid-thigh and has long lines in the front. This is a great option for wearing with your favorite sneakers.

Bell-sleeve top + cigarette pants

Wear a bell-sleeved top with a pair of cigarette pants if you want to take your retro look. As I mentioned earlier, the bell at the bottom of the sleeves will help to elongate your look when they hang down. 

Meanwhile, the fuller cut at the top of cigarette pants helps to hide a larger midsection stylishly. Since these pants get closer to your leg from the knee down, they will not make your legs look bigger. 

Accentuate your ankles by wearing this with your favorite strappy sandals. When choosing your top, select one that does not end directly on your waistline, as that would make it look larger.

Empire-waist dress + ballet flats

One of the most classic looks is to wear an empire-waist dress with ballet flats. This outfit is so easy to dress up or down that you will find yourself wearing it often. Consider an option with a wider waistline as it will help camouflage this area.

Woman posing outdoors blue dress

These dresses particularly look great on women with strong upper bodies. You can opt for one with a halter top if the straps are wide enough to support you properly. Options with V-necks are also an outstanding choice. 

But you will want to avoid ones with a round or scoop neck. When made from silky materials, these often make fabulous mother-of-the-bride dresses.

In the next chapter, I will share some concluding thoughts about what older women who have enjoyed and are enjoying food should wear. Therefore, I encourage you to keep reading.


People often talk about a youthful glow when they see a young woman. The truth is that there is also something special about the glow of a mature woman who has spent a lifetime working and loving others. If that describes you, then I hope you now have a better idea of how to dress if you are over 50, especially if you are overweight

Women, if you have a friend who needs a little encouragement to help them dress more beautifully, share this post with them. They will love that you cared enough to help them look radiant.

If you have any questions, I would love to answer them. It is the way that we all learn together, so do not be shy.

While waiting for a reply, check out some of our other fashion posts.

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