First dates can be nerve-racking, but nailing your first date outfit can boost your confidence. Not sure what to wear on a date? Here are the must-knows!
Congratulations, you have an upcoming first date! Although this is very exciting, we know just how stressful it can be. How do you make a good first impression, how do you avoid embarrassing yourself… and what do you wear on a first date?!
Finding the perfect thing to wear can be the worst. You don’t want to wear something too fancy that you scare them off, but you don’t want to dress too casually that you look like a slob.
You’re probably pacing back and forth in your closet looking for the perfect thing to wear to impress your date. But don’t let your worries overshadow the excitement because we’re here to help.
If you want to know what to wear on your first date to make your date sit up and take notice of you the very second you walk in, here are some things you’ll need to consider.
[Read: 23 first date conversation tips to flirt with and impress your date in minutes]
Things to consider when picking out a date outfit
First dates are all about first impressions, so you’ll want to do your best to leave a good one. If you’re struggling to find the perfect outfit, here are some things to consider when browsing your closet for your big date.
1. Dress for the occasion
Do you know where you’re going for your date? Unless it’s a surprise date, you should definitely know so you can plan your outfit out appropriately. [Read: Where to go on a first date – 85 best first date ideas that are fun & romantic]
If you show up in a tuxedo to a casual date, you risk embarrassing your date or even making them feel uncomfortable. And don’t forget to check the weather as well! The last thing you’ll want to be wearing for a beach date outside is a thick wool sweater.
So, consider the location of the date, the theme, the temperature, the time of day, and what your date might also be wearing.
2. What does your date like?
Do you know your date well enough to make a judgment call? Does your date like girls who wear pink, or men who wear turquoise?
If you know your date’s preferences, see if you can wear something they may like. It shows that you’re taking an additional interest to be likable. And everyone likes a date who takes initiative. [Read: Blind date – what it is, how it works & 26 must-know blind dating secrets]
3. Wear clothes that show who you are
You are dressing up and thinking extra hard about what to wear on a date because you want to make an impression, right? So, focus on choosing an outfit that really shows who you are.
If you really want to make an impression, accessorize your outfit with something more personal that lets your personality shine through.
Handcrafted jewelry, a cute headband or clip, great-looking shoes, your favorite color or pattern, etc. It could be anything as long as it gives your date an insight into who you are.
And one of our most important pieces of advice is don’t wear something that isn’t you. Making a good impression can be intimidating, but if you go above and beyond to wear something that doesn’t truly represent you, you’ll send your date mixed signals and even confuse them.
4. Clothes that make you feel good
All of us have clothes that make us feel and look good. You have your favorite blouse or jeans too, right?
If you can’t make up your mind on what to wear, or if you find yourself feeling huffy while deciding what to wear, then your best bet is to wear something that you already love. [Read: How to be comfortable in your own skin – 20 ways to love being you]
5. Pieces you’ve already worn before
Choosing clothes you’ve already worn before not only boosts your confidence, but it saves you from being uncomfortable.
If you pick out a piece you’ve already broken in, you’re sure to feel comfortable and confident as opposed to a tight-fitting new outfit that hasn’t been broken in yet.
So, ditch the falling straps or tight waistline. After all, an uncomfortable rash or painful blisters are the last things you’ll want to deal with while on your date!
6. Be prepared
Now, not all dates are going to be confusing, but if you’re wondering what to wear on a date that’s a surprise, you need to be prepared.
Surprise dates are not usually casual dates *think walk in the park or dinner in a restaurant*, so keep a few things handy in your car just in case.
Think variety. If you’re wearing tennis shoes, bring a pair of sandals or hiking shoes. If you’re wearing jeans, prepare a change of clothes that are looser like shorts. And if you’re wearing a sweater, always layer it over a T-shirt underneath!
7. Don’t overthink it
Listen, we know the entire process of planning for a date can be stressful. But try your best not to overthink it. Really, regardless of what you pick out to wear, your personality should do most of the talking.
With that being said, don’t shy away from wearing something you feel confident and comfortable in. The most important thing is to be yourself, be confident, and let your personality shine through! [Read: First date nerves – 18 ways to not be nervous for a date & feel calm]
The do’s and don’ts of what to wear on a date for women
Oftentimes, the clothes you wear on a date also subtly convey who you are and what you want out of the date. And that’s why many women put a lot of thought into what they wear.
What’s the message you want to convey? Would you like to show your date that you’re fun, hip, and casual? Do you want to appear sophisticated and classy?
With all these things that come into your mind as you prepare for your date, it’s very easy to go over the top. That’s why we’ve compiled a list of do’s and don’ts for picking out your outfit. [Read: 42 flirty first date tips for girls to leave a guy smitten & wanting more]
1. Do show off your assets discreetly
When it comes to first-date outfits, a certain level of modesty can leave your date wanting to know more. However, don’t assume you need to be covered head to toe. If you’re proud of one of your assets, show it off!
The key word here is one. Pick one of your favorite assets to show off so you reveal just enough to keep your date hooked.
Maybe it’s your shapely shoulders, never-ending legs, or something else. Whatever it may be, choose something that will accentuate your asset discreetly. [Read: How to show off your boobs & get them noticed without looking trashy]
2. Don’t show too much skin
Now, we did say you should show off your assets, but that doesn’t mean you should go in practically nude.
Avoid wearing anything too revealing or too fitting, or you may just end up making your date feel uncomfortable and embarrassed. It’s a first date, you have a lot of other dates and nights after dates to reveal skin. So play a clean game.
3. Do go for the classics
Classic clothes never go out of style. The reason so many trends are in place is so the fashion industry always has something to market as the next big thing, but you don’t always have to follow these trends.
Just go for clothes that feel good and look good on you. It’s much better than following trends that are neither comfortable nor flattering. Trust us when we say that men aren’t too keen on the latest trends, so they’re more likely to notice clothes that look great on you instead of the latest thing Kim Kardashian is wearing.
4. Don’t wear something overly fashionable
Now you may be sitting on the front row of every fashion week, but unless you’re dating a fashion designer, skip wearing anything that’s too flashy or fashionable.
Wearing a bird on the head may be comfortable in Sex and the City, but it’s not in real life. And Doja Cat may be able to pull off eccentric outfits splashed on all the tabloids, but let’s be real, you’re not Doja Cat.
So, skip skimming through beauty magazines for the latest celebrity styles and just go with what clothing shows your personality.
5. Do wear tights with short skirts and dresses
Zooey Deschanel knew exactly what she was doing when she showed up on the big screen as the opposite of your typical hot vixen. Her fashion style revolves mainly around feminine wear with the added touch of black or navy tights.
Tights let you show off how toned your legs are without showing the world what’s going on beneath that skirt. It’s the perfect balance of sexy and feminine.
However, make sure your bottom half is covered! It may look good when you’re posing in front of your mirror, but the problem is that you might end up exposing yourself when you move around.
Just imagine trying to slink down off a bar stool in a super short skirt! And don’t get us started on wearing a flowy short skirt on a windy day! [Read: 37 girlish secrets to be more feminine & draw others with your softer side]
6. Don’t wear anything that needs double-sided tape
You’re on a date, not a red-carpet movie premiere! It’s best to save those outfits for another occasion, particularly one where you get your own personal assistant to watch out for clothing mishaps. Besides, anything that requires double-sided tape is just begging for a wardrobe malfunction!
7. Do wear less flashy clothes
You’re already out on a date with someone you could potentially hit it off with. So there’s really no point in wearing something as attention-grabbing as a dress bedecked in jewels, sequins, and glitter.
You wouldn’t want your date to take one look at you and instantly become blind, would you? Flashy and glittery clothes are better off worn at a club or a rave, not at a quiet restaurant with your date.
8. Don’t wear sportswear
Okay, so you’re an athlete. That’s pretty cool. But looking like you just got out of the gym wouldn’t be very appealing to your date.
Yes, it shows your date that you’re a fitness fan, but it also shows that you can’t be bothered to wear something nice when you’re going out with someone.
Besides, wouldn’t it be better if he found out that you’re a fitness buff by seeing that you’ve got a toned physique? [Read: Gym crush – 17 ways to approach a guy & get him interested at the gym]
9. Do go for casual wear
Gym clothes are very comfortable, that’s true. But there are a ton of other clothes that are just as comfy as gym clothes.
For instance, you can wear a lightweight cotton shirt with a pair of jeans and flats. You don’t always have to give up fashion for comfort!
10. Don’t wear too much makeup and jewelry
Deciding what to wear on a date isn’t just about clothes, it’s also about your makeup and your jewelry. In your haste to impress, try not to overdo your accessorizing and beautification.
Wear a thin layer of makeup and keep the jewelry to a minimum. Over-exaggerating style statements will only make your date break into a sweat.
11. Do wear accessories
If you’re the type of girl who loves to get her glam on, you can still do it in a more tasteful way. Keep your outfit relatively simple and stylish, but adorn it with key pieces.
Examples of these key pieces are a statement necklace, dangling earrings, or a few rings. They’re not too flashy, but they’re still eye-catching and appealing.
12. Don’t apply too much hairspray
We know how important it is to keep your hair in place, but making your hair as hard as a helmet may not be the way to go.
Remember, you want to be comfortable. Not only is using a lot of hairspray bad for your hair, but it can also be tough to get rid of in the shower.
13. Do go for a simple bun or natural hair
You’re not aiming to look like you’re in a photo shoot, so why all the fuss about keeping all your hair in place? Instead of the very 1960s look of hairspray-drenched styles, go for a low and slightly messy bun.
The tendrils that frame your face can actually be very flattering, and it gives you a very romantic vibe. Perfect for a date! [Read: 55 tips & things to do on a first date to leave your date smitten & in awe!]
14. Don’t wear uncomfortable footwear
What’s worse than wobbling around while you go for a walk with your date? Not only will you be more prone to embarrassing and potentially painful accidents, but you might go home with a tiny colony of blisters on your feet.
Yes, those sky-high stilettos and ankle-breaking wedges might look great with your dress, but there are other options.
15. Do wear comfortable yet fashionable shoes
There’s a reason you’re allowed to try on shoes before buying them: so that you can get to choose the pair that are comfortable to walk in. Instead of shoes that stretch your arches to their limit, go for shoes that have soft insoles.
If you’re not a heels girl, opt for cute flats or kitten heels. Your feet will thank you for them. [Read: How to dress sexy – 29 subtle & classy ways to make them lust for you]
The do’s and don’ts of what to wear on a date for men
Just as women put effort into finding the perfect outfit for their first date, guys do too. They get just as anxious picking out the perfect thing to wear because, let’s be honest, how a guy dresses can either be an instant turn-on or turn-off.
To point you in the right direction, here are tips to ensure you wow your date from the second you walk up to them! [Read: 46 BIG first date tips & rules for men to charm her & make her fall for you]
1. Do keep it simple
If you’re a simple guy, keep it simple. Of course, what you wear depends on where you’re going on your date and the season. However, you don’t want to overdress if that’s not who you are.
Jeans, slacks, a sweater, long sleeve shirt, or a plain t-shirt. Keep the colors simple, and you’re good to go. Just, please, don’t wear a suit unless you know your date specifically wants you to! [Read: How to be more attractive to women & 72 traits that make you VERY desirable]
2. Don’t be afraid to wear special occasion pieces
Yes, we just said to keep it simple, but if you’re the type of guy who has clothes reserved for special occasions, don’t be afraid to break them out.
Slacks, a nice colored top, and classy shoes are all pieces that show you put extra effort into looking nice for the person you’re going on a date with.
3. Do wear a fitted and versatile top
The infamous solid-colored button-down is perfect for any date scenario. It can be dressed up, or it can be unbuttoned and dressed down. If you choose this option, be sure to avoid crazy colors or patterns.
A single-colored, fitted crewneck top is also a safe choice if your date is more casual than not. This kind of shirt does well on any kind of date involving physical activity or good weather.
Just keep in mind that the less busy the top, the better. Excessive patterns can be distracting and take away from other aspects of your outfit. With that being said, a neutral-toned top can make you look classy and sophisticated. These colors are versatile and easy to build outfits around.
4. Don’t forget to layer
Okay, so you’ve chosen a collared shirt for your first date, good choice. But don’t forget to layer! Always wear a fitted shirt underneath any button-up shirt or overshirt, regardless if it is long-sleeved or short-sleeved.
You want to piece your outfit together based on adaptability. A nice fitting undershirt may be useful if the venue of your first date is too warm for comfort. The same goes with a light bomber jacket or flannel, you never know when you’ll get cold! You’ll thank us later for this tip.
5. Do leave the “funny” shirt at home
You may think wearing a tuxedo t-shirt is hilarious, and it probably was when you were twelve. But you’re not twelve, so don’t wear one.
That being said, any, “I’m a doctor, let me check you out” or “FBI: Female Body Inspector” t-shirts are also a horrible idea.
Come on, man, if you walk into any place to meet your first date, you better have a fantastic personality to pull that off. Because you’re going to need it. [Read: What do girls like in guys? 30 desirable traits & turn-offs women hate]
6. Don’t wear holes
Jean jackets and pants with holes in them may be trendy, but you should steer clear of them when it comes to picking out the perfect first-date outfit.
Yes, we know the holes were put in the denim on purpose. No, it doesn’t look any less trashy. And holes in your shirt? Not even a question—no.
7. Do aim for slim-fit denim
If you’re wondering what to wear on a first date, denim can be your savior. Of course, you can wear light denim pants, but opt for dark denim. It gives off a more sophisticated and cleaner look. Plus, you’re able to match much more with t-shirts and jackets when you have a pair of dark denim jeans.
Slim-fit is the safest option for your choice of bottoms. This way, you aren’t baggy or saggy. Not only that, but slim-fit denim accentuates your best features. This is a universally attractive style of jeans! [Read: How to get any girl to notice you without even talking to her]
8. Don’t wear joggers
Even if your date is casual, joggers are a no-go. The difference between wearing denim on a casual date and wearing joggers is that a good-fitting pair of denim elevates your look, whereas joggers don’t.
In fact, joggers are closer to sweatpants than they are denim. We know it hurts, but keep the joggers in the closet for your first date.
9. Do go for a nicer shoe
Despite how ridiculous it may seem, shoes are everything. Your shoes say everything about you, and they’re one of the most subtle signs of your personality. Will your date look at your shoes? Absolutely, even if they’re not thinking about it.
So, the nicer the shoe the better. Boots and derby shoes match well with slacks or chinos for an uplifted look, and they pair well with denim for casual looks too. This kind of shoe shows that you planned for the date, even if you’re pairing it with a casual top. [Read: 40 secrets & easy hacks to look rich & dress like you’re rolling in cash]
10. Don’t wear dirty sneakers
Okay, we’ll acknowledge that dress sneakers do exist, and sometimes, they pair nicely with a casual outfit. But make sure you bring your best white sneakers.
When picking out what to wear for a first date, you want to leave a good impression. And white sneakers that you’ve clearly taken care of show that you can upkeep things in your life. Dirty and scuffed sneakers do not.
11. Do be hygienic
The last thing you want is for your date to start wondering about your personal hygiene. That isn’t a good sign.
Your personal hygiene shouldn’t even be a thought in their mind when they see you. So, make sure you’re showered, have shaped your facial hair, and have your hair styled. It takes fifteen minutes, literally, but will make a huge impact on her opinion of you.
12. Don’t overdo the cologne
Picking out the perfect cologne can be tricky. Yes, you love this cologne but how do you know they will? Or better yet, do they have any allergies to perfume? That would be a great disaster on the first date.
It’s up to you to decide which kind of cologne best suits your first date. Our tip is to match your cologne scent with the overall theme of your date.
And for sure, spritz yourself with some cologne and use some aftershave but don’t douse yourself in it. You don’t want to drown your date in the smell. [Read: How to wear cologne, the secrets of cologne chemistry, and how to use it right]
13. Do wear a watch
Now, a watch is a perfect accessory that is subtle but leaves a lasting impression. Regardless of the kind of watch you’re wearing, it is going to catch your date’s eye. So, make sure it pairs well with your outfit.
Watches can be dressed up or dressed down, so they can be worn for any type of date. Plus, wearing a watch shows that you are capable of paying attention to detail and can appreciate the finer things in life.
14. Don’t go Jersey Shore with accessories
There’s nothing wrong with wearing these accessories, but you want to make sure you don’t look too flashy or blingy.
If you show up to a first date covered in diamonds *or whatever your expensive jewelry of choice is*, you risk looking like a money-hungry douche. Sorry, it’s harsh, but it’s true.
Keep the watches, gold chains, rings, and bracelets to a minimum. Rule of thumb: make sure your accessories match your clothing. [Read: 36 classy, essential accessories for men to go from boyhood to adulthood]
15. Do avoid hats and sunglasses indoors
In movies, a guy who walks into a room in shades or a hat is mysterious and cool. But that’s not reality. If you walked into your first date wearing either of these things indoors, you will automatically be labeled an asshole. Sorry, we don’t make the rules.
By wearing a hat or sunglasses indoors, you give off the impression that you’re closed off and unapproachable—two things that you don’t want to be on a first date! Lose the shades and the hat so that your date can see your face.
Outfits for different types of dates
Of course, knowing what to wear on your first date depends largely on where you’re going for the date. For a little more guidance, we’ve come up with popular first-date locations and what you might consider wearing to them.
1. Daytime coffee date
Casual clothing is perfect for a coffee shop first date. Keep the look simple with a neutral shirt, a tailored coat *if the weather calls for it*, and a nicer pair of boots.
If you’re a guy, this is a great opportunity to opt for chinos if your shirt is more casual than fancy. And if you’re a girl, a warm skirt with tights underneath is the perfect aesthetic to match the café!
2. Casual dinner date
You can’t go wrong with denim and a comfortable, fitted cotton shirt on a casual dinner date, whether you’re a guy or a girl.
Since you and your date aren’t preparing for a fancy night out, clean white sneakers and a light overcoat are also great ideas. Keep it simple for this date, but not too simple.
Think, effortlessly attractive.
3. Post-work drink date
If your date is taking place after work, we hope you had time to plan your outfit before going into the office. If not, no worries! You can transform your professional attire into a more appropriate date look by simplifying your top and keeping your bottoms.
Guys, take off the blazer if you’re feeling up for it, and unbutton a few of your shirt buttons while you’re at it. Don’t worry if you still have your slacks on, they will contrast well with your now-casual top.
Ladies, statement accessories or a bold lip color can help transform your business attire into a classy and sophisticated date night outfit. [Read: Sneaky sex at work – the pros and cons of banging on the job]
4. Elevated dinner date
If you know you’ll be going to a fancy restaurant for your first date, this is the time to bring out your special occasion pieces.
Stick to dark-colored clothing to keep your look classy. A date night dress paired with heels or elegant flats is perfect for the girls. And for the guys, a button-down shirt and dark denim is your best friend for this kind of date.
5. Picnic or outdoor date
Girls, this is the perfect time to bring out any pretty, flowy dresses you have in your closet! Pair your dress with a cardigan or light overcoat if the weather calls for it.
And if your day will be full of walking, your feet will thank you if you pass on the heels. Try sandals or flats to match your accessories.
And guys, an airy short-sleeved button-up or a polo shirt paired with lightweight chinos or linen shorts will compliment your date’s attire for a picnic or outdoor date. Don’t shy away from keeping this look casual but vibrant and classy. [Read: 23 fun, romantic summer date ideas to warm your date’s heart]
6. Pub date
A pub date is an exciting date to plan an outfit for because you have a little more freedom in what you wear.
Of course, you don’t want to be over-the-top, but this setting lets you be a little more unique. Choose a fun and comfortable outfit for this one. Worry less about what’s appropriate and more about what makes you feel and look good!
7. Movie date
Choosing the best outfit to wear to a movie date is all about comfort! So, pick a comfortable yet well-put-together outfit.
A cozy sweater paired with casual pants or a skirt and comfortable sneakers or warm boots is the perfect combo for this kind of relaxed date. [Read: Movie date – how to build sexual chemistry & create a perfect date]
How to truly master the perfect first date outfit
First dates can be tense, tricky, and nerve-racking. The best way to combat all of the awkwardness that comes with a first date is by feeling your best. This means, wearing what makes you feel the most confident and ditching the things that don’t.
Yes, we just gave you some guidelines to follow when picking out what to wear on your first date, but they’re only guidelines. At the end of the day, you should dress in whatever makes you feel the best and most like yourself.
If you don’t feel comfortable in dresses, wear a jumpsuit. Not a fan of skirts? Wear pants. Hate walking in heels? Wear sneakers. Do buttons on your shirt irritate you? Wear a graphic tee. Can’t stand the feeling of fitted denim? We hate to say it, but wear the joggers!
No matter the article of clothing, don’t wear it because you think you have to. Stay true to yourself and the rest will follow. That is how you can master the perfect first date with your outfit.
[Read: 30 first date rules for guys & girls that’ll make your date adore you]
While trying to figure out what to wear on a first date, remember to keep it comfortable and keep it classy. Always plan ahead of time to make the best of your first date outfit. And most importantly, be yourself!
