What to wear on a first date: 19+ Men & Women Outfits

What to wear on a first date - faverie

Imagine that you just got a text message inviting you on a first date or that you have agreed to go on a blind date. Once you agree, you start panicking about what you will wear on the date.

A survey of 2,000 adults shows that women go on first dates an average of 11 times before they are content that they have found the right one. Meanwhile, men go on an average of 15 dates before they find the person they want to date regularly.

Therefore, knowing what to wear on a first date is essential. We’ve written this post to help. Let’s jump right in!

First date outfits basics & FAQ

Many people feel jittery when they go on a first date and wonder if they are about to meet the person with whom they want to spend the rest of their life or are about to meet the wrong person again.

Regardless, making a great first impression is vital because you never get a second chance to impress someone instantly. Therefore, you should spend time picking out your first date outfit, and arming yourself with some information can help.

What’s a first date outfit?

A first date outfit is an outfit you would wear on a first date. You should wear an outfit that makes you feel self-confident because we all know the jitters that come with first dates. Secondly, it should be an outfit that looks terrific on you.

The first rule in picking out a first date outfit is to choose one that makes you feel fabulous. Do not wear an outfit where you constantly have to adjust a strap or pull it up or down. 

You want to feel great because everyone knows that first dates can be extremely rough. Even if the person you are meeting is not the right one, you may catch the eye of someone perfect for you.

Additionally, you want to choose an outfit that looks good on you, and wearing an ugly one can sabotage the date before it gets started. If you are wider than you like, avoid wearing horizontal stripes.

You should also avoid wearing large-print outfits unless they seem to break into smaller images when a viewer gets closer. If you want to appear taller, wearing vertical stripes can be a great plan. If you want to draw attention to your waistline, select an outfit you can wear with a narrow belt.

The perfect first date outfit also is appropriate for the venue where the date is occurring. Many first dates occur at casual restaurants, and you will want to select an outfit that is colorful and stays close to your body. 

You will also want to consider the weather. If the date is happening at a restaurant or other indoor venue, select an option that you can wear with a blazer or sweater to put on if you get cold.

Why is it important to wear the right outfit on a first date?

Most people form a first impression in under 7 seconds. Therefore, you need to choose an outfit that looks exceptionally sharp on you. It is also vital that your makeup looks great with the outfit that you are wearing. Spend a few extra minutes styling your hair so that the person you meet sees a beautiful complete picture.

Couple women smiling drinking

While scientists may argue about the length of time you get to make a first impression, it is always under 30 seconds. From that point forward, everything gets measured against the first impression filter during your date. Therefore, it must be a positive one.

While some people will tell you that they notice a person’s eyes or smile first, psychologists believe that a person sees the overall appearance first. Therefore, every aspect of your outfit must work perfectly together.

One of the first things a person will notice on a first date is the quality of your clothes. They subjectively see a person wearing high-quality clothes as a successful individual they want to get to know better. 

Except in very particular circumstances, like a 1980s-themed party, you want to wear clothes that are in current fashion. At the same time, ensure that your outfit does not give off the impression that you are part of a group unless you want the other person to think that.

As I mentioned earlier, you do not want the person to think that your grooming needs improving, so take time to ensure that your makeup is perfect and that you smell great. Instead of wearing an expensive perfume that may bother the other person’s allergies, a trick I love to use is to wear lavender essential oil. 

You can combine it with a carrier oil. Then, rub it on your wrists and pulse points so that you smell great. Since lavender has a calming effect, it can help keep your emotions in check if you tend to get nervous before a first date.

What should you consider when picking your first date outfit?

The venue is the most crucial factor to consider when picking out a first-date outfit. You want to choose an outfit that is appropriate for the place the meeting is occurring, and choose an outfit that looks great and that you will enjoy wearing.

One of the things that you should consider when selecting your first date outfit is your body’s shape. You will want to pick outfits that make you look your best, and you should always aim to balance your body. Furthermore, you should use lines or patterns to focus attention on your body’s strongest assets.

Woman posing dress street

Choose outfits that help people focus on your waistline if you are an apple shape. One-sleeve and no-sleeve tops help draw your date’s attention toward your face. If you need a sweater or jacket, choose one that ends below your waist and has strong vertical lines. High-waisted pants will make your legs look longer.

Alternatively, add volume to your upper half if you have a pear-shaped body. A great solution is to wear sleeves with some volume to them, like batwing or dolman. Choose a top with a wide neckline or a cowl-neck top. Choose tailored pants that elongate your bottom half. Straight or bootcut is usually the best choice in jeans.

Hourglass figures look particularly great in structured tops. While you can choose a long jacket with a belt, you will usually look better in a short coat that stops about your waist. Choose a pair of trousers or jeans with design details highlighting your waist.

Inverted triangle body shapes need to pay particular attention so that their hips and shoulders look balanced. When choosing a jacket, make sure it makes your hips look slightly broader. Attract attention to your lower half by choosing pants that end about your ankles. Then, pair them with a fabulous pair of shoes or ankle-high boots.

If you have a rectangular body, choose the asset you want to emphasize. A sweetheart neckline is an excellent choice because it creates the illusion of curves. Select trousers with a wider leg.

What accessories to wear on a first date?

The right accessories can help you look more polished, which is essential on a first date. Choose options depending on where you are going. You should also consider your body shape.

Apple-shaped women want to draw attention away from their larger midsection, and large earrings can help. You may also want to wear hair accessories to attract your date’s attention up to your face. Bags with longer handles help to make your midsection appear smaller.

Pear-shaped women look great in just about any style of earring. When choosing necklaces, opt for choices that end about your bust if you have a great one, or select ones that end about your waist if you want your bust to appear smaller. 

If you wear a belt, choose one that fits just under your bust or low on your hips. Choose a handbag with a long handle and carry it below your waist.

The best necklaces for hourglass women either hug the neck or hang down to form a deep V. Do not choose belts that go around your natural waist as they will make it look even smaller. Choose a handbag that ends about your natural waistline. Opting for one with some angles can add volume to your body.

Women with an inverted triangle-shaped body will want to wear large rings, like cocktail rings, to draw attention away from their upper body. Long pendant necklaces and jewelry around your ankles and toes can also be a great choice. Wear a medium-sized or large belt to define your waist. Select a handbag that ends on your hips or upper thigh.

A rectangular-shaped woman can wear almost any jewelry. Consider large earrings and hair accessories to draw your date’s attention upwards. Especially if you have a small chest, consider combining several necklaces of different lengths to make it look larger. A round handbag gives the illusion of curves.

Men will want to consider where they are going on a date and choose the right accessories for that venue. If you are going to a casual dinner, opt for colorful socks or stick a colorful pocket square in your suit coat’s pocket.

Should you wear makeup on a first date? What to consider?

Consider where you are going on a date before deciding about your makeup. Generally, you will want to wear a little makeup but shy away from unique looks on a first date. You will probably want to avoid heavy makeup.

Portrait woman smiling makeup

If your skin is feeling a little dry, then moisturizer can help. Make sure that you work it into your skin. Add a little foundation if you think you need it. Then, set everything with powder. Consider adding a highlighter instead of blush to your cheeks to bring out a little color.

Pink lipstick is a fabulous choice. Try outlining your lips with a similar color before filling them in with the pink lipstick. A terrific option for many women is wearing nude lipstick and putting a little clear gloss over the top.

Assuming that you are going on a casual date, then use a color of eyebrow pencil that is like your natural shade on your eyebrows to make them look fuller. Use a mascara brush to brush out your eyelashes in the direction that they naturally grow.

Apply a basic color of eyeliner to your eyes’ creases. Then, pick a slightly bolder color and apply it just under your eyebrow. Finally, select a color very similar to your skin’s tone and use it to contour your eyes.

Steal a moment to inspect your makeup before heading in to meet your date to ensure that everything works great together.

What’s the best color to wear on a first date?

Assuming your date is at a casual diner or event, you should wear colors that work well with your skin tone. You will also want to consider the season because you should wear darker shades in the winter and brighter colors during the summer. Spring is a great time to wear pastels, while harvest colors are perfect for fall.

You can apply some basic ideas to decide if you have warm or cool skin tones. If your veins are purple, your eyes have blue or gray flecks, and your natural hair color has gray or ash undertones, you have cool skin tones. 

Sticking on the cool side of the color wheel is usually an excellent choice for you. Otherwise, you have warm skin tones, and the warm side of the color wheel is perfect for you.

If your skin is extremely fair, consider wearing neutrals, pastels, and jewel tones. If your skin is fair, consider wearing lavender, seafoam green, blush, soft yellow, mint green, coral, ivory, and peach. 

Women and men with fair skin tones will want to consider wearing olive, purple, mustard, cranberry, forest green, royal blue, and pink. If your skin tone is olive, stick to earth tones, green, orange, olive, blue, navy, pink, emerald, and burgundy. Jewel tones, white, fuchsia, yellow, royal blue, and blush are ideal for dark skin tones.

While keeping these basic concepts in mind, you can find many ideal options for a first date. In the next chapter, we will look at some of them. 

Therefore, there is no need to cancel your date as long as you keep reading because you will fall in love with these ideas. It is specifically designed to help you select options that will look nice on you, which is a great way to relieve some of that first-date stress.

First date outfit ideas for women

In the last chapter, we looked at some general ideas about first-date outfits and why choosing the right one is invaluable. We also looked at accessories that worked well with first date outfits and what colors to wear. Now, let’s focus on some outfit possibilities.

Have you ever been invited to a meeting or an event, and you have picked out several outfits, but none of them seemed right? Then, you go to a clothing store and wander around aimlessly because you have no idea what you are even looking for.

I want to take that stress out of choosing a first date outfit, and I have several suggestions so that you can pick your favorite. Then, when it comes time for the date, you will know that you look fabulous. In this chapter, we will look at ideas for women. Men, your turn will come in the next chapter.


A blazer and jeans are a great choice to wear on a first date. Remember to pick jeans that look great on you. For example, if you are an apple shape, consider wearing mid-rise jeans with stomach control. 

If you are pear-shaped, choose boy cut and relaxed-fit jeans that make your legs look longer. Women with hourglass figures will want to choose jeans that flare out a little. 

Ladies with inverted triangle-shaped bodies can wear almost any type of jeans. If you have a square or rectangle-shaped body, opt for high-or-low-rise jeans.

You can wear almost any color of a blazer on a first date, so think about the color suggestions I made based on your skin tone in the last chapter. If you have a larger breast, choose one with a plunging neckline or an open-front option. 

Women who have small breasts will want to consider blazers with larger lapels because they will make their breasts look more prominent.

Blouse + jeans

A pretty blouse is a perfect top to wear with your jeans on a first date. While I gave you some advice in the last chapter on selecting blouses, let’s dig a little deeper. Apple-shaped women will want to choose blouses that accentuate their shoulders, neckline, or bust.

Woman sitting bench park

You will also want to consider blouses that help define your neckline. Alternatively, it is essential to emphasize your upper body while defining your waist if you are a pear shape. Blouses with voluminous sleeves can be a great choice, or you may want to choose a blouse that has a large neck opening, like a boat-or-square neck. 

Fitted tops are often an excellent choice for women with hourglass figures. Women who are inverted triangles will want to choose tops that define their waist and make their necks look longer.

Consider the color of jeans you want to wear on your date. If you have any doubt, sticking to a medium blue is usually a safe bet.

Skirt + turtleneck sweater

If your first date is happening in a casual environment, select a skirt ending about your knees or a little higher. If you have an apple shape, consider a skirt with ruffles around your waist, as it will help balance out your body. 

Mini skirts look fabulous on rectangular-shaped women, and the short hemline will show off your legs, while the tightness will help showcase your curves. 

Many body types can wear a pencil skirt, but they look particularly fabulous on women with hourglass figures. The flair of an A-line skirt makes it look amazing on a pear-shaped woman.

You can choose between several styles of turtlenecks, but the classical turtleneck is often the safest bet. The droopy neckline of the cowl-neck sweater makes it an excellent option for women who need to emphasize their upper body. 

Consider a funnel-neck option if you are uncomfortable in a turtleneck that fits tight around your neck. While most turtlenecks are a single color, a first date can be a terrific time to wear a printed one, like a leopard print.

Dress + heels

Since you never get a second chance to make a first impression, wearing a dress that fits your body well can be a terrific option. As with skirts, if your date is a casual one, you will want to select one that ends about your knees. 

If you need to enhance your upper body to balance out your look, consider dresses with embellished necklines, sleeves that have some dramatic flair to them, or one with an eye-catching belt. If your upper body is one of your strongest assets, then strapless options look great on you. Consider mini dresses as you have the perfect body for them.

Kitten heels are ideal for a casual date when paired with your dress. Depending on your outfit, you can choose between pumps, sandals, or mules. You may even want to wear kitten-heel ankle boots.

Bodysuit + pants

If you have curves that you want to show off, then a form-fitting bodysuit can be a great option. On the other hand, if you are a little self-conscious about one, consider it a base layer and add a jacket over it. You can also wear it with a kimono. This is particularly a great look if you tend to be on the chunky side because of its long lines in the front.

You can wear pants with bodysuits. There are at least 16 different styles of women’s pants, so you can easily find an option you love. If you need to camouflage your stomach, then high-waisted options are great. If you are proud of how your legs look, choose slim-cut options. Low-rise trousers are a fantastic choice if you need to elongate your upper body.

T-shirt + sneakers

A t-shirt is a fantastic choice for a first date. A collared t-shirt is ideal for pairing with jeans or your trousers. They look more formal than a collarless tee, so they are also ideal for pairing with a casual skirt. If you are going to an outdoor venue and you have a great stomach, flaunt it a little by wearing a cropped tee. 

You can wear a denim shirt over it if you wish. A V-neck tee, especially one with a pattern, is easy to pair with many bottoms. A cold-shoulder t-shirt is a wonderful choice if your upper body looks fantastic.

You can wear sneakers on a first date. Canvas sneakers look fantastic when paired with a t-shirt and a denim skirt. Designer sneakers, especially those with a bit of bling, are a great way to draw attention to your legs. 

Leather sneakers look fabulous with mini skirts and are usually very comfortable. In most cases, you do not want to wear your athletic sneakers on a first date unless you are going to play some sports together.

Jumpsuit + heels

A jumpsuit is an excellent option for a first date because you do not have to worry about constantly pulling your top down. Be careful not to choose one with so much fabric that it swallows you up if you are short. On the other hand, if you are tall, then a wide-leg option is ideal. 

An off-the-shoulder option is perfect if you have a great upper body. If your midsection needs some help, think about an option with some flow at the top. One with a belt right under your bosom can help. V-neck jumpsuits will help your bust look smaller, especially ones with a deep V cut.

Pairing your jumpsuit with heels is a great option. When you are putting together your outfit, consider the color wheel. Find the primary color in your jumpsuit and go straight across the color wheel. 

Then, move one space to the left or right to find the split complementary color. Make about 30% of your wardrobe this color. Wearing heels and carrying a matching handbag in this color can be a fantastic choice.

Pullover top + trousers

A beautiful pullover top is an excellent choice for a first date when you pair it with trousers. You can choose between many different styles, and you can find long-and-short-sleeve options. 

One of the reasons that I like to wear tops is that I do not have to worry about buttons coming undone and my date seeing things I do not want them to see at this point in our relationship. When choosing a top, think about the different textures available. 

Usually, those with rougher textures, like knit tops, are fantastic to wear with cargo pants or jeans. Meanwhile, those with a smoother texture, like linen, are ideal for wearing with dress trousers.

When choosing your trousers, consider options that are neutral colors. That way, you do not have to worry about matching the colors on your top. I especially love to wear brown pants with a pink top and gray pants with a blue top.

Capris + flats

There are many types of capri pants, like pedal-pushers, clam-diggers, and ankle pants, so you can easily find an ideal option for your date. While the choice is up to you on which length you want to wear, avoid those that stop at the thickest part of your calf.

Detail shoes floor

They will make your legs look short, and you certainly do not want that. If you have muscular shoulders, choose a pair that hangs a little away from your legs to help balance your look. On the other hand, if you are tiny on the top, choose a pair that lies close to your body.

I like to wear capris with my flat shoes. While you can wear them with heels, I prefer flats because if I have to run away from a bad date, they are easier to move in. Especially if you are going to a casual restaurant, a colorful option is a great choice. One of my favorites is to wear a black monochromatic outfit, then wear leopard-print flats.

Crop pants + kitten heels

While capris stop at or above your calf, crop pants stop at your ankles, and they are another fantastic choice to wear on a first date. These pants look best when they are fitted to show off your legs. 

Therefore, you should be careful to avoid options that are too baggy for you. Manufacturers make these pants from various materials. I especially like wool options for a first date because they look a little classier than ones made from denim. Then, choose a top that works well with the texture of your crop pants.

Kitten heels look great with crop pants, allowing you to move quickly. You can choose between closed-toe options or sandals. If you put on your cropped pants and kitten heels and think that your legs look short, try wearing the outfit with taller heels, but be sure to choose a choice that you can walk in well.

Women, you now have fantastic outfit ideas for a first date. In the next chapter, I will do the same for guys. After all, many need some fashion advice so that they do not end up on a date wearing their stinky gym clothes. Therefore, be sure to keep reading.

First date outfit ideas for men

In the last chapter, we spent time looking at different outfits that women could wear. While it may be fair to say that women worry more about these things than most men, guys still need to be concerned about what they wear on a first date.

Just like your first impression of a woman, she will form her first opinion of you in 30 seconds or less, and if you want the relationship to go anywhere, it cannot be a bad one.

Never fear, guys. This chapter will help you pick the right clothes for a first date. I have an excellent friend who went on a blind first date. She says that when she walked into the Italian restaurant and saw her date sitting at a table with his white dress shirt and black trousers, she knew he was the right one. 

They will soon celebrate their third wedding anniversary. She did not have time to get to know his award-winning personality or his great sense of humor. Instead, her first impression was based on his appearance, and the same can happen for you when you wear the right clothes.

Slim fit chinos + crewneck tee + sneakers

There are tricks to picking out the right chinos for a first date. If you are going to a casual restaurant or event, pick ones with flat back pockets. The pants should fit properly around your waist so they do not fall down. 

Additionally, you should not need a belt to hold them up. You should be able to pinch between 1 and 1.5 inches of fabric on each side of your thighs. There should be a slight break between the end of your chinos and your sneakers.

Pairing your chinos with a crewneck tee is a great idea. The shirt will make your shoulders look square if your shoulders have a little slant. It will also make your neck look leaner and your face slimmer.

Wearing this outfit with your sneakers is a great idea. Just make sure that they are clean and do not smell. Select a neutral-colored pair that is different from your shirt or chinos.

Polo shirt + chinos + loafers

A polo shirt can be an excellent choice for a first date if it fits you correctly. You should choose one that ends about mid-zipper in the front and mid-pocket in the back. It should look fitted to your body. But it should not be too tight. 

You should be able to pinch 2 inches of fabric on each side of your stomach. The sleeves should end about halfway between your shoulders and your elbows.

I just covered a lot of material on choosing chinos that fit you properly, but it is vital to choose the right color. Generally, chinos in a light color are ideal for a casual first date, and beige and khaki chinos are always a great choice.

Loafers are a great footwear option. Choose a pair in a neutral color that does not match your chinos color. If you want to add some pizzazz to your outfit, consider a metallic pair in a neutral color.

Trousers + dress shirt

A great pair of trousers and a dress shirt worn with your oxfords make an outstanding outfit for a casual first date. Your pants should fit you properly. There should be room to put one finger under the waistband, and they should not need a belt to stay in place. 

Ensure that there is enough room in the hips but that fabric does not pool in this area. If buying new trousers for your first date and the material pulls or pools, you need a different size. The trousers’ rise should follow your body’s natural outline. If it does not, you will get a wedgie, and boy, that can hurt.

When buying a dress shirt, consider the style that will look best on you. If you have a lean torso, choose a slim-fit dress shirt. Most people will look best in a regular fit, and a loose fit is perfect for a casual first date. 

The armholes should start right at your shoulders, the hemline should be above mid-thigh, and the collar should lie about 1.5 inches away from your neck.

Blazer + dress shirt + jeans

Topping your dress shirt with a blazer and wearing it with your jeans is another fantastic option. I have already had a lot to say about dress shirts, so let’s consider the style of blazer that you should wear on a first date. 

The quality of a man’s clothing is one of the first things a woman will notice. So spending money on a classic blazer is a great choice. I think a navy blue one is best if you can only afford one option. Choose one with gold or other colored buttons that contrast with the blazer. 

Ensure that the shoulder seam does not extend beyond your shoulder. You should not be able to fit anything bigger than a baseball into the chest area when the blazer is buttoned. A double vent is more flattering on most men.

You can pair the blazer and dress shirt with a great-fitting pair of jeans. You should choose a shirt that is a shade or two lighter than the color of your blazer, which is another excellent reason to choose a navy blazer. The jeans should fit close to your body. Opting for a pair with stitching in a different color is usually best.

Hacking jacket + jeans

I love the look of a hacking jacket. It is almost a sports jacket, but the pockets are put on at a slant. Additionally, these jackets are often plaid, which is an excellent look for a casual date. 

Choose one of the colors in the jacket to wear as your shirt color. Otherwise, you will get too many colors going on in your outfit. Avoid wearing other clothes with patterns when you wear a plaid hacking jacket.

You will want to wear your hacking jacket and shirt with your jeans. I have already discussed how jeans should fit, but let’s discuss wearing different colored jeans. Muted colors are ideal for cooler months, while you can wear more colorful ones in the summer. 

The darker the color of the jeans, the more formal they will appear. Gray jeans are ideal for wearing with most hacking jackets, and they are easy to dress up or down depending on the impression you want to give your date.

Polo + dress shorts

Depending on where you are going on your first date, a polo shirt and dress shorts can be a fantastic option. If you have a paler skin tone, consider wearing a light gray polo shirt because it will not wash your skin tone. 

Man model posing shorts polo

If you have olive skin tone, you can wear almost any color, but inky blue and pink look fabulous. On the other hand, dark skin, navy blue, and khaki look fantastic on you.

Dress shorts, particularly those that look like chinos, are ideal for a smart casual date when you pair them with your polo shirt. If the weather is a little cooler, tie a sweater around your neck so that you can put it on if it gets cooler, or you can be a gentleman and offer it to your date.

Leather jacket + oxford shirt + trousers

Since you want to give the impression of someone who wears high-quality clothing, the cut of your leather jacket is particularly important. Manufacturers make cheap leather jackets to fit as many people as possible because they need to mass market them. 

Instead, choose a leather jacket where the shoulders help square up your look and are not too big on you. Select a jacket with high armholes as it is not as likely to slip when moving. The sleeves should end between your wrists and your thumb’s base. Unless you are a tall man, opt for a leather jacket that ends about your waist.

Put the leather jacket on with an oxford shirt. Ensure that the shirt has a soft, S-curled button-down collar. You want to wear a shirt that is 100% cotton. Opt for a choice that has a box pleat as they allow you to move better. 

Finally, select an option with a barrel cuff, making the shirt appear more casual. You will want to wear this look with your favorite dress trousers.

Sweater + khakis

Opting for a quality sweater and wearing it over a dress shirt and your khakis makes a beautiful first date outfit. While the sweater should hug your body, it should not restrict your movements, so be sure to stretch and move in it before your date. 

Your sweater should end about mid-thigh. You will also want to choose a sweater that has a flattering neckline. A V-neck looks excellent if you are a little short, while a boat neck will help you look thinner.

When choosing khakis to wear with your sweater, opt for choices with a mid-rise as they will look better on you than those that come up over your stomach. They should have two pockets in the front and two in the rear. 

Avoid options with pockets on the sides because they are cargo pants. While it’s a fine line to walk, khakis can still be worn if they show minor wear, but you do not want to wear ones that are noticeably distressed on a first date.

Turtleneck + corduroy trousers + sneakers

A turtleneck is a fantastic option for a casual first date, especially when pairing it with corduroy trousers. Choose one that is medium or heavyweight depending on the weather because a skinny one will show every body flaw. Keep your outfit casual by leaving it untucked.

Wearing corduroy trousers is a great choice to wear with your turtleneck on a casual first date. A beige turtleneck looks fantastic with burgundy corduroy pants, and blue looks great when paired with gray cords. 

Blue corduroy pants are an excellent choice when creating a monochromatic outfit. A black turtleneck is a fantastic choice when paired with mustard-yellow cords.

This is a fantastic outfit to wear with your sneakers. You can give it a vintage edge by pairing it with high-top sneakers. Alternatively, choose a pair of corduroys that end about your ankles and wear them with your designer sneakers.

Now that you have some possible outfit ideas, let’s take a look at some dos and don’ts when choosing an outfit to wear to a first date. While I will give you my suggestions at the end of this post, I would love to hear about dos and don’ts that you try to follow, so be sure to keep reading.

Do’s and don’ts

It may help you finalize your first date outfit to keep some general do’s and don’ts in mind. You can think of this as a final checklist to see if the outfit you have picked is perfect for a first date. If it passes this list, then it is good to go. Don’t forget to take care of your grooming and ensure that your clothes look and smell fantastic.

Picking out the right first date outfit is stressful, and I highly recommend you lay two or three outfits out and work through this checklist. Choose your favorite if one does not naturally rise to the top. Hopefully, the first date will turn into many more, and you will have a chance to wear them later.

You will want to choose an outfit that makes you look great because you may be spending the rest of your life with this person. On the other hand, you may be like my friend Cheryl. While she picked out a perfect outfit, the guy turned out to be a real loser. 

Yet, the waiter thought she was so cute that he dug around until he contacted her, and they have been together for three years.

Do wear something comfortable

First dates are stressful, and you do not want to have to be thinking about your clothes constantly. Therefore, you should avoid wearing any outfit you must continuously be tugging up or pulling down.

Couple watching each other cafe street
Source: Good Faces on Unsplash

You should also avoid outfits with bows in the front, embellishments that move, and other details that tempt you to fidget with because dates can be nerve-racking. Instead, choose outfits cut right for your body silhouette and stay in place regardless of how you move. These outfits will look great on you.

Do balance out your body

Your top and your bottom need to be equally balanced. If you wear something wide on your top, then wear something wide on the bottom. For example, if you wear a shirt with batwing sleeves, then wear wide pants, but if you are wearing a turtleneck, wear leggings or slim-fit jeans on the bottom. 

If you want to wear wider pants or trousers and a slim-fitting top, then consider balancing out your body by adding a handbag that you can carry above your waist. Women, you can also use eye-catching earrings to balance out your look.

Do wear the right colors

Most first dates are casual events, which is the perfect time to wear a colorful outfit. If you are afraid that your outfit will become too loud for your comfort zone, consider pops of color. 

For example, wear a black monochromatic outfit and add bright yellow shoes and a handbag. A great way to choose colors that work together is to select complementary shades. For example, make 60% of your outfit one color, 30% another color, and 10% a third color. 

For instance, if the primary color is red, go straight across the color wheel and find the opposite color, green, but do not choose it. Instead, move one space up and one space down to find your other colors, which in this case are blue-green and yellow-green.

Do choose outfits that fit your body shape

Every person’s body is a unique creation, so wear clothes that accentuate the positive and camouflage the negative. For example, if your bust is your strong suit, wear a colorful pattern in this area and a solid color across the rest of your outfit. 

Wide belts and ruffles can help camouflage a large stomach. If you have a great midsection, consider wearing a thin belt or outfits that cut across your middle. 

If you are a bit overweight, thin horizontal stripes can make you look slimmer. Manufacturers make beautiful outfits in many styles, but not every style suits everyone.

Do consider the formality of the date

Most first dates are casual, but that is not always the case. Therefore, make sure you know about the formality of the event. For instance, someone may know that you are an art lover and invite you on a date to an art show opening with a formal dress code. 

Alternatively, someone may know that you are a fitness buff and ask you to run in a 5k race with them. Therefore, you must consider where you are going on your date. Ladies, generally, dresses and skirts that end above the knee are ideal for casual first dates. 

However, those ending below the knee usually have a more formal vibe to them. Guys, blazers, and sports jackets are often suitable for a casual date, while suits are often needed for more formal occasions.

Don’t overlook the weather

Especially if you live in a climate where the temperatures change a lot, be sure to consider the weather. You do not want to wear a sweater to an event when it is 100 degrees outside. Likewise, do not wear a crop top without a coverup if the weather is going to be under freezing. 

Choosing a layered outfit is often a great idea. That way, you can adjust your outfit throughout the date. Additionally, you never know when you might end up at a venue that is super cold, even in the middle of the summer. 

Think about your footwear if it has been raining and you are going somewhere that requires walking. High heels may get stuck in the ground. 

Don’t forget to accessorize

Guys and gals need to wear accessories with their first date outfits. Remember that you must wear sunscreen, sunglasses, and a brimmed hat whenever you go outside. As I mentioned earlier, women should wear accessories that help balance their looks. 

Therefore, if your outfit stays close to your body, wear small earrings, like studs. Drop earrings are a great choice if your outfit lies further away from your body. Likewise, you should choose a handbag that works with your body shape. 

Those that end above the waist are an excellent option for women who need to add emphasis to their upper body. Guys, the only accessory you may need for a casual first date is a quality wristwatch.

Don’t wear your lounge clothes

A first date is a special occasion. Therefore, you should wear nicer clothes as it reflects greatly on your date’s first impression of you. While it is not necessary to buy new clothes for every date, you will want to wear stylish clothes that are clean and neat. 

If you need to iron your clothes, then do so as wrinkles will leave a wrong first impression. Likewise, if any of your clothes have rips, missing buttons, or other issues, get them fixed before your date or choose a different outfit. Assuming that you are not going to a themed party, ensure that your outfit is fashionable.

Don’t be afraid to show your personality

While I have given you many suggestions about first date outfits, I cannot personalize them for you. Therefore, you should add touches to any outfit to make it your own. Sometimes that may be wearing a particular color you adore or horse-themed earrings because you love horses. 

Men can do the same thing by wearing socks with a picture on them or wearing a small design on their belt buckle. Adding these touches is a quick way to let someone know about your interests, and it can be a fantastic way to start a conversation.

Don’t stress too much

First dates should be fun. Therefore, do not stress so much about what you are wearing that you cause yourself to have a nervous meltdown. If you are wearing new clothes, put it all on for a couple of hours a day or two before your date. 

Woman smiling holding yellow jacket

This will give you time to make last-minute adjustments if something does not look right. You should also ensure that your shoes are clean and well-polished. 

Then, keep the outfit together so that you know where everything is before your date. Even if your date is not the right one, think about the marvelous venue you got to visit.

We have looked at a lot of first-date outfits. I will discuss options to wear to particular venues in the next chapter. Therefore, you should keep reading.

What to wear on a first date depending on the occasion

Now that you have some ideas of possible outfits to wear the next time you go on a first date, let’s get more specific about what to wear to particular venues. As you probably already know, some outfits look better in some places than others. Therefore, to make an outstanding first impression, it is vital to consider where you are going on a date.

According to research by the Pew Research Center, only about 15% of people are interested in finding a companion for a committed relationship. Therefore, if you find you are in this group, then it is imperative to choose the right outfit so that you can move forward with your life. Wearing the right outfit on your first date can undoubtedly help.

Daytime coffee date

A coffee date is meant to be a casual get-together. Therefore, jeans are an ideal solution for both men and women. Women may want to wear it with a batwing top. In that case, she should choose jeans that have some flair to them. She will want to carry a handbag that hangs below her waist and her drop earrings. Kitten heels are a great choice. 

Men may want to wear it with a beautiful turtleneck. In that instance, slim-cut jeans are best. A wristwatch with a leader band, a leather belt, and leather Chelsea boots are great additions to the outfit.

Casual dinner date

Many dates start with dinner in a casual restaurant. Women may want to wear an A-line denim skirt and a colorful button-up blouse. Drop earrings will add a little pizzazz to the outfit. Consider wearing open-toe sandals with a bit of heel and carrying a crossbody bag. 

Men may want to consider wearing their dress shorts and a polo shirt. Dressy moccasins or leather boat shoes are great footwear choices. If the weather is a little chilly, consider wrapping a sweater around your neck. Adding a messenger bag can be a great option.

Formal dinner date

Depending on how formal the dinner is, men will want to wear a suit coat and matching trousers to the formal dinner. Choose one in a conservative color, like navy blue or black. A white dress shirt is usually the best option, but skip ones with barrel cuffs. Put on your tie and wear a gold or silver wristwatch. 

Women will want to wear a dress that comes at least to their knees. Fix your hair in an updo, and choose your best jewelry that matches the dress. High heels are required footwear.

Post work date

A post-work date can be challenging if you do not have somewhere to change. A terrific option is to wear a bodysuit under a blazer to work. You can wear a skirt and your heels. Then, take off the skirt and heels after work and put on a pair of animal-print trousers and your flat sandals. Wearing black onyx jewelry is a great idea.

Woman smiling camera street holding phone

Guys may want to swap out their solid-colored work blazer for a plaid one. If the plaid is large, wear a matching pair of socks in a smaller print. Your oxfords are a great footwear choice.

Cocktail date

For guys and women, denim on denim is a terrific look for a cocktail date. Ladies will want to choose slim-fitting jeans and top them with a long denim shirt that buttons up the front in a different shade. Then, wear the outfit with a pair of black ballet flats. 

Meanwhile, guys want to wear a denim blazer over a light blue button-down shirt. Then, wear a different shade of blue jeans on the bottom. Suede leather boots are ideal for wearing with this outfit. They could also make the outfit look more casual by wearing a blazer over a t-shirt.

Picnic date

A flowy floral dress is a perfect option for a woman to wear on a picnic date. I especially like options with a boat neck when worn with a simple gold necklace. Then, put on your kitten heels. 

If the weather is a little chilly, wear a cardigan over the dress. This look is particularly great when you choose a pretty pastel dress in the spring and one in a harvest tone in the fall. 

Guys will want to wear blue jeans and a polo shirt on the picnic. Sneakers are ideal for your feet but do not wear your nasty athletic shoes.

Cinema date

A tunic sweater and your leggings are an excellent option for the movies. If the tunic is a solid color, this is the ideal time to wear a statement necklace. Then, pull your hair back with some gold barrettes.

Woman looking camera jewelry

Men will want to wear a turtleneck sweater and corduroy trousers. Tuck the turtleneck in and wear it with a belt without a design. Black and brown belts are usually ideal. You can wear your sneakers with this outfit or choose a pair of casual boots.

Sports game date

A sports game date can be a lot of fun to dress for because you should wear your favorite team colors. If the game is held outdoors, then wear a team t-shirt under a denim jacket that ends about your waist. Leave the t-shirt untucked and wear it over your favorite blue jeans. 

A baseball cap is perfect if you are headed to an outdoor game, and don’t forget your sunglasses. Guys can wear a very similar outfit, but if the date is a football game, they may want to wear a sweater in the team’s colors, skinny jeans, and sneakers.

Festival date

Women look great when wearing a jumpsuit to a festival. Choose an option in a color that looks great on you. Since you will probably be doing a lot of walking, this is a great time to wear your flat sandals. You will also want to wear your sunglasses and a hat. The best hats have a wide brim all the way around them. 

Depending on your outfit, choose a statement necklace and matching earrings. Guys will want to wear their jeans to the festival with a crew-neck shirt. The color choice is up to you if it looks good on you. You may also want to consider wearing a leather thong necklace.

Speaker date

Heading off to hear a speaker can be a fun first date option because it gives you something to talk about afterward. Ladies, consider wearing a blazer over a button-up shirt and your pumps. Keep your makeup and jewelry choices conservative. Your closed-toed shoes with a bit of heel are a fantastic choice.

Portrait woman smiling silver necklace
Source: Prince Akachi on Unsplash

Men will look fabulous in their sports coats and dress trousers. A button-down shirt is a great choice to wear under the jacket. Oxfords are a great choice for footwear.

We have covered a lot of material since this post began. In the next part, I will give you the option to ask any questions that you have and ask you for a couple of favors, so keep reading.


I hope you have enjoyed reading this post because the first impression someone has about you is often based on your appearance. 

Now, you know how to put outfits together that will help you look your best. If you have any questions, please ask them. I love to help people learn.

If you have a friend ready to go on a first date, share this post with them. They will love learning the information too.

While you are waiting for your next first date, read some of our other posts. They will help you look fabulous in every aspect of your life.

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