How to Dress Casually for a First Date (Guys)

Co-authored by Lisa Shield and Kyle Hall

Last Updated: March 7, 2022 References

You want to look good for your first date that’s coming up, but how do you dress to impress in a casual way that doesn’t make it look like you’re trying too hard? Don't worry—it's possible to both dress casually and look amazing at the same time for a first date. To help you out, we’ve put together a variety of casual date outfits that exude confidence and coolness. We’ve also got all of the do’s and don’ts when it comes to dressing casually for a first date so you're set up for success.

Section 1 of 2:

Casual Outfit Ideas for a First Date

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The casual coffee date outfit: This is the perfect laid-back outfit for your next coffee date. Pair dark-wash jeans in a slim fit with a white t-shirt. Throw an open button-up shirt or flannel on top.^{[1]
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Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.} Finish your outfit with a clean pair of white sneakers or canvas shoes.^{[2]
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- Alternative outfit: swap the button-up shirt with a denim jacket and wear black slim-fit jeans instead.
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The casual dinner date outfit: If you’re going out to dinner with your date, dress up your casual outfit a bit. Wear a clean, wrinkle-free button up shirt with a pair of dark-wash or black slim-fit jeans.^{[3]
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Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.} If you’re going to a nicer restaurant, try a pair of tailored trousers instead, and tuck in your shirt. Finish your outfit with boots or clean white sneakers.^{[4]
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- You can’t go wrong with a crisp, white button-up shirt.
- Unbutton the top 2-3 buttons of your shirt for a sexy-casual vibe.
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The casual “grabbing drinks” outfit: To look sophisticated but casual at the bar, pair a solid sweater or t-shirt (depending on the weather) with well-fitting trousers and some classic white shoes or sneakers. Complete the look with a bomber jacket and you’re good to go.^{[5]
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- Sure, you could wear jeans, but a nice pair of fitted trousers will elevate your outfit without making it look like you’re trying too hard.
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The casual outdoor summer date outfit: Prints and short sleeves are a classic summer combo. Try pairing a print short-sleeve button-up shirt with dark-wash jeans, chinos, or even a pair of shorts. Wear clean sneakers, high-tops, or oxfords to complete the look.^{[6]
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The casual winter date outfit: If it's going to be chilly out for your date, try wearing a fitted dark sweater with dark-wash, slim-fit jeans and a pair of chelsea boots. Finish the look with a stylish peacoat (and maybe even a scarf).^{[7]
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Section 2 of 2:

Tips for Dressing Casually for a First Date

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Go for a fitted silhouette. Whether you’re wearing jeans and a t-shirt or a button-up and trousers, choosing clothes that fit you just right will help you make the best impression on your date. Your clothes shouldn’t be baggy, but they shouldn’t be skin-tight either. Wear clothes that fall somewhere in between.^{[8]
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- A good rule of thumb is that you shouldn’t need a belt to hold up your pants. If you do, they’re probably too baggy.
- Slim or straight-leg jeans are a classic, flattering fit. Jeans should have a slim fit around your thighs and then taper gently from your knees down.
- A button-up shirt shouldn’t be so tight that it’s constricting. If it doesn’t stay tucked into your pants when you put your arms behind your head, it’s probably too small.
- On the other hand, a button-up shirt shouldn’t be loose and billowing. If the shoulder seams are lower than your shoulder bones, the shirt is probably too big.
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Opt for dark, neutral colors when in doubt. It’s hard to go wrong with dark neutrals like black, charcoal, navy, brown, and khaki green. These colors are easy to match with, and they’ll make you look more sophisticated and put together.^{[9]
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- Jeans with a neutral color t-shirt and bomber jacket on top is a perfect laid-back date outfit.
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Choose casual shoes, but make sure they’re clean and scuff-free. Gone are the days where you’re expected to always wear oxfords, tasseled loafers, or other dress shoes on a first date. If you’re keeping things casual on your upcoming date, a clean pair of high tops or sneakers is perfectly acceptable. The important thing is that they’re clean and scuff-free—you still want to look put together even though the date is casual.^{[10]
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- Wearing dressier shoes, like oxfords or Chelsea boots, works too. They can help balance out your outfit if you don’t want to look too casual (like if you’re taking your date out to dinner).
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Wear clothes that are clean and wrinkle-free. This is important no matter how casual or fancy a date is.^{[11]
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Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.} A wrinkled shirt or jeans with stains on them will distract your date from what’s important (getting to know you!). Once you’ve chosen your date-night outfit, double-check that each piece is clean and free of wrinkles before you head out the door.