What to Wear on a First Date: The Go-To Outfit for Men

So, my good man, you find yourself with a first date looming. First of all, congrats are in order. Secondly … what the heck are you going to wear? Finding exactly what to wear on a first date is a tall task that revolves around where you’re going and what you’re doing. And spring, with its fluctuating temperatures and tricky weather, is as tough a time to dress. Take it easy on yourself. Better yet, take the guesswork out of what to wear on a first date. That much we can help you solve.  

The outfit below works for a dinner that’s casual-yet-cool or drinks that lean fancy, but don’t call for a jacket and tie — either situation sounds like your kind of place, no? If that’s the kind of date you’re looking for, our picks for what to wear are sure to please you— and impress your partner.

WP Standard Denim Jacket – $119
wp standard denim jacket what to wear on a first date

Ditch your blazer in favor of a denim jacket in a just-right shade of blue. It’s made from Cone Mills denim, so it’s limited-edition and sure to toe the line between casual and dressy.

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Best Made Co. Featherweight Buttondown Shirt – $118
best made co featherweight button down shirt what to wear on a first date

Is this classic cotton Oxford slightly pricey? Sure. But will it work handsomely on any date, be it your first or your fifth? Yes, it certainly will. The bright, white color is crisp and the collar will frame your face nicely. Plus, the shirt can easily be worn on its own. If you need more suggestions for white button-downs, we’ve got you covered.

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Flint and Tinder 365 Pants – $98
flint and tinder 365 pants what to wear on a first date

With the clean, simple cut of your favorite pair of denim and the kind of comfort and stretch you need on the daily, the 365 Pants from Flint and Tinder really are a great pair of everyday trousers. However, the fact that they aren’t the typical blue jean color will stand out when you’re trying to make a first impression.

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Allen Edmonds McAllister Wingtip Oxford – $275
wingtip oxford what to wear on a first date

Where will your date’s eyes be drawn towards (beside your own, that is)? If we had to bet, we’d guess your feet (or to the watch on your wrist, but that’s not the point). You need shoes that are practical, but classy. These beautifully made wingtip Oxfords strike the right balance between too flashy and too casual.

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Arvin Goods No-show Socks – $8
arvin goods no who socks what to wear on a first date

Because the weather’s bound to get warmer at some point, we’re going to recommend you flip up the cuffs on your Flint and Tinder 365 Pants and show off some ankle, courtesy of these cool, comfortable Arvin Goods no-show socks.

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Taylor Stitch Minimalist Billfold in Canyon – $98
taylor stitch minimal billfold what to wear on a first date

Whenever the check comes, get ready to whip out this lovely Taylor Stitch wallet. It’s an everyday carry masterpiece, but it’s also the right kind of accessory for any date.

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Nezumi Studios Bailene Watch – $500
nezumi studios watch what to wear on a first date

With style that’s both a bit rugged and a bit refined, this entry-level investment watch is a lovely pick for this casual outfit as it won’t detract attention from the rest of your ensemble.

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With any luck, this first-date look will secured you a second and third dates, or even a full-on relationship. If that’s the case, may we suggest pulling out this playlist for your one-month anniversary.

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