How to Dress on a First Date for Guys

Co-authored by Taissha G. LaReau and Hunter Rising

Last Updated: March 6, 2022 References

Are you stuck staring at your closet figuring out what to wear to impress your date? Even though you could just throw on the same clothes you wear every day, putting in a little extra effort into your outfit makes you stand out even more. Luckily, you can pull together a really attractive style in just a few minutes. Keep reading for some inspiration on outfits that you can make with some clothes you already have!

Section 1 of 5:

Consider Where You're Going

You want to match the vibe of your date and the location. You’d wear different clothes on a bowling date than you would if you were going out to a nice restaurant. If you’re keeping it casual with a movie date or walking through the park, it’s okay to dress down a bit. For something a little more upscale, you’ll probably want clothes that are a bit nicer.^{[1]
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Expert Source

Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.}
- If you’re doing something active, athleisure clothes are perfect for you.
- Check the weather before you go out on a date. If it’s going to be chilly, don’t show up wearing only a T-shirt.
- Blacks, neutrals, and earth tones match the vibe of a date night.^{[2]
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  Expert Source
  
  Taissha G. LaReau
  Wardrobe Consultant & Stylist
  Expert Interview. 31 January 2022.}

Section 2 of 5:

Focus on the Fit

Clothes that fit well will always accentuate your body better. Rather than putting on clothes that are a little too big or small, update your wardrobe with some new fits. Your clothes should hug your body without feeling too tight. A tailored jacket, straight-leg jeans, or slim-fit shirts are all perfect for showing off your bod.^{[3]
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- Clothes that fit well also help you look and feel good so you’re more confident around your date.

Section 3 of 5:

Pay Attention to Details

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Putting a little extra effort into your look shows that you really care. If you take a few extra seconds to check yourself out in a mirror before you go, it can go a long way. Iron away all the wrinkles in your clothes, use a lint roller to pick up any loose fuzz, and try on a few accessories. When you feel confident about your looks, you’re ready to go!
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Accessorize with a watch to look more professional and confident. Watches show your date that you pay attention to the small details of your outfit. If you have a few watches to choose from, stick with a minimalist style that isn’t too flashy for a classic look. Just slide it onto your wrist so it fits tightly to finish your outfit.^{[4]
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- Analog watches tend to look better than fitness trackers or smartwatches. If you only have a smartwatch, use a simple, classy watch face so it has a clean appearance.
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Your date will love it if you have a good-smelling cologne. A little spritz of a signature scent can go a long way and help you stand out to your date. On a daytime date in the summer, look for a cologne that has a light, refreshing or citrus scent. Save your stronger, more sensual cologne for a formal dinner date or a night out on the town.^{[5]
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- Only apply a small spritz of cologne so it doesn’t get too overpowering.

Section 4 of 5:

Casual First Date Outfits

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Rock a comfortable henley shirt for a casual coffee date. Henleys are soft textured shirts with a buttoned collar, and they fit tight to show off your body. Try out a light-colored short-sleeved henley if you’re going on an outdoor summer date, or wear a black long-sleeved fit if you want to dress up a little bit more. Complete your outfit with a nice pair of chinos or jeans and a nice pair of shoes.^{[6]
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- Henleys look great when you layer jackets on top of them. Try a black leather jacket with a charcoal henley and some jeans.
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Dress up a relaxed fit with a flannel. Just layering a flannel over a T-shirt shows that you’re putting more effort into your outfit than normal. Find a stylish, checkered flannel in your favorite color and rock it with a pair of jeans and sneakers. Since flannel is such a soft fabric, it’ll be really tempting for your date to reach out and touch you.^{[7]
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Expert Source

Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.}
- If you want an attractive casual style, try a red flannel with a plain white or black tee underneath with a dark-wash pair of jeans and some white tennis shoes.
- To dress flannel up a little bit, look for a style with a simple pattern and wear it on top of a plain undershirt. Put on a pair of neutral-colored chinos and some dress shoes to finish your look.
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Layer up with a leather or denim jacket if it’s going to be chilly. A nice jacket can work really well for just about any outfit whether it’s casual or formal. If you want to go for a classic “bad boy” look, you can’t go wrong with a black leather jacket and a white tee underneath. Denim gives off a great, rugged look, so try pairing it with a flannel button-up and chinos.^{[9]
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Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.}
- Try not to wear any graphic tees underneath your jacket since it may make you seem underdressed. A solid color will work better.
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A pair of slim-fit pants go with tons of outfits no matter the occasion. Jeans are extremely versatile and work for casual or formal dates. Get a pair of jeans that hug your legs pretty tight so they don’t look baggy or bunch up by your feet. If you need to, you can always cuff your pants above your ankle for a really stylish look that shows off your shoes.^{[11]
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- For an eye-catching outfit, try a burgundy henley with a pair of jeans and some clean white tennis shoes.
- Dress your jeans up with a button-up shirt, belt, and a stylish boot.
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Put on a nice pair of clean sneakers for casual or semi-formal dates. White trainers are classic shoes that work really well no matter what you’re doing, but any plain sneaker matches most outfits you’d wear. Try pairing your sneakers with jeans and a henley for a really casual date, or put on a pair of khaki chinos and a flannel for a slightly dressy style.^{[12]
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- Be sure to get rid of any stains or scuffs from your sneakers before you wear them out so you have a nice and clean appearance.

Section 5 of 5:

Formal First Date Outfits

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Buttoned shirts look great no matter what you’re doing. Any button-up shirt can fit into a casual or formal date depending on how you dress it up.^{[13]
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Expert Source

Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.} You can wear either short- or long-sleeved button-up shirts based on the weather or where you’re going for your date. Just be sure to iron out all the wrinkles before wearing your shirt out so you look nice and clean. ^{[14]
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- For a casual date in the summer, put on a short-sleeved button-up without an undershirt and leave the top button or two undone to show off your chest. Finish your look with a pair of jeans and a pair of sneakers.
- If you want a formal look, tuck a long-sleeved button-up into a pair of chinos or dress pants and put on a belt. Complete your outfit with some nice dress shoes or boots.
- Roll the sleeves on a long-sleeved button-up for an even more stylish look.
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Dress up for a dinner date with a turtleneck or V-neck sweater. If it’s later in the evening or cold out, break out your favorite sweater to wear out. Solid colors or simple patterns work best since they aren’t too distracting to look at. Try out a few different looks with different types of sweaters to see what really makes an outfit pop.^{[15]
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- For a slightly casual look, put on a cable-knit sweater with a clean pair of dark-wash jeans and sneakers to finish your look.
- If you want a real formal look, layer a black V-neck sweater over a button-up shirt. Finish your outfit with khaki chinos and some dress shoes.
- Stay away from wearing hoodies on a date since it might look a little too casual.
3
Blazers work great when you want to look more put together. Full suits are a bit too formal for a first date unless you’re going somewhere really swanky, but you can still rock a blazer jacket no matter the occasion. Stick with solid colors or simple patterns rather than bright, eye-catching looks since they could make you seem a little overdressed.^{[16]
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- If you want a slightly casual look, button up a flannel and wear a plain blazer on top. Finish your look with a nice pair of jeans and some sneakers.
- For a business casual look, you could rock a blazer on top of a black turtleneck sweater along with a pair of chinos or dress pants.
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Try some colored chinos if you want to go for slightly dressier pants. Chinos come in a ton of different colors, but some good shades to get include black, khaki, and navy. Whenever you want something a little more fancy than jeans, put on your chinos with your favorite shirt and shoes for an instant good look.^{[17]
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- For a casual date, wear a short-sleeved button-up with some khaki chinos and some simple sneakers.
- If you’re going out for dinner, try putting on a muted cable-knit sweater with some black chinos and dress shoes.
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Dressy boots complete a formal outfit for a big night out. Stylish boots are perfect if you want the perfect middle-ground between sneakers and dress shoes. Wear a pair of boots that match with the rest of your outfit so they don’t clash. Boots instantly add some classiness to your look whether you’re wearing jeans, chinos, or dress pants.^{[18]
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- For example, you could wear a black sweater and blazer with khaki chinos and black boots.
- For another formal outfit, try layering a red sweater over a light button-up. Put on a pair of jeans and some dark brown boots to finish your look.

Expert Q&A

Question

What should a woman wear on a first date?

Taissha G. LaReau
Wardrobe Consultant & Stylist
Taissha G. LaReau is a Wardrobe Consultant & Stylist based in Albany, NY. With more than three years of experience, Tai specializes in helping people maximize their wardrobes by creating functional, everyday outfits that are tailored to their lifestyle and make them feel polished. While she offers virtual and in-person closet editing, personal shopping, and outfit creation, she also has a knack for helping people shop strategically, discover new brands, and experiment with new styles. Taissha holds a BS in Marketing from The State University of New York College at Oswego.

Taissha G. LaReau

Wardrobe Consultant & Stylist

Expert Answer

Try mixing sexy pieces with casual pieces! You might mix a pretty top with some jeans, or pair a more casual top with a skirt. You could also try a body suit—something fitted on the top with a more relaxed bottom.