Date Night Outfit Ideas for Men

Date Night Outfit Ideas for Men

Dating can be weird. Don’t get us wrong, it’s fun and exciting, but you never know what to expect on a first date. Now that online dating is the norm, there’s even more pressure when you’re meeting that person face-to-face for the very first time. What do you talk about? Where do you go? Are they going to look like their photo? What in the world do you wear? Let us take the pressure off a little bit by giving you some fashion advice to make the right first impression so your next first date is not a swipe wasted.

couple on a date in hawaii

What to Wear

Think Active

Look, we all agree: Sitting at a table and staring directly at each other for an hour and a half can be pretty awkward, and nobody wants that. Planning a more laid-back or active first date can loosen you up and get the sparks flying. There’s more opportunity for that oh-so-subtle arm touch when you’re playing mini-golf, throwing axes, getting down with some shuffleboard, etc.. Plus, doing something new or different not only shows how fun and interesting you are, but it also gets rid of some of the pressure of that crucial first date, especially when you don’t even really know each other yet.

Even if your date is laid back, your outfit shouldn’t be. That doesn’t mean you need to go all out with a suit and tie—and, actually, that’s a definite no, too. Remember that scene in Step Brothers when they show up to the interview in a tux? Yeaaaa...—but a T-shirt is just a tad too low-effort for a first date. First impressions are important, so dress to impress. A simple sport shirt is perfect because it has a bit dressier but is comfortable enough to wear during almost any activity, even if you plan to get a bit sweaty.

Pick the Right Pants

This is actually the easiest part of dressing for your first date. Once you’ve nailed down which men’s sport shirt you’re going to wear, just pair it with the right pair of khaki shorts with a solid-colored polo shirt and you’re ready to go. Easily dress up your jeans to nail this look.

Accessorize Skillfully

Unless you’re taking her to a wedding, a gala or a funeral (tip: don’t), then ditch the tie. It’s just too formal in most first-date situations. That doesn’t mean you should slum it, though. If you’re planning something a bit more special, you might consider throwing on a sport jacket. Don’t opt for the full suit (again, too dressy), but a classy gray or navy blue blazer with a pair of chinos may just help you score that second date.

Have you heard of K.I.S.S.? No not the band, the acronym. It means “keep it simple, stupid” and you should keep it in mind when picking out accessories for your first date outfit.  When it comes to men’s outfit accessories, we recommend you stick to just a classy watch with a leather band. Don’t wear a baseball cap. This, again, falls into the same category of “way too casual” for a first date- Unless you’re actually headed to a baseball game, which could be a fun way to spend the first date.

couple taking photos on beach in hawaii

Our Favorite First Date Outfits

We realize that we’ve hit you with a lot of information on how to dress (and how not to dress) for your date. The appropriate attire is obviously going to change depending on where you’re going and what you’re doing, but here’s a couple of outfit ideas to get you started.

The Laid-Back Look

A pair of men’s canvas pants in an interesting color like forest green will help you show off your unique style and keep you comfortable no matter what your date night activity is. Think you’re going to be too hot in long pants? Go for a pair of cotton Oxford shorts. For a shirt, think along the lines of a casual button-down or a nice polo. Just remember, a laid back look doesn’t mean you can show up to your date in that plain white tee that you wear around the house with the ketchup stain on it. An outfit that’s too casual sends the message that you didn’t care enough to dress it up. Sports shirts and lightweight button downs are comfortable, casual and still classy. And don’t you dare even think about wearing sweatpants.

couple in bahamas on street

The Sophisticated Style

If you’re going to dress it up, you should probably stick with long pants. Pick a pair of chinos (light or dark color, depending on what color jacket you’re going for) and add a blazer. Don’t underestimate the shirt that goes under the jacket. You’ll probably end up taking your jacket off at some point in the night, and you’ll want a shirt that’s just as nice underneath. Try a collared sport shirt to keep you cool or a patterned button-down.

Confidence is key during a first date—no matter how nervous you might be before. Pick out an outfit that leaves you feeling sharp and self-assured. Then, show up early and just be yourself. We’re sure you’ll nail it.

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