How to Dress for a First Date for Men Back on the Dating Scene

How to Dress for a First Date for Men Back on the Dating Scene

Getting dressed for a date, especially when it’s been a while since you’ve been on one, can be a challenge, to say the least—men's button-down shirt or t-shirt? Jeans or khakis? You may worry about the line between looking like you made an effort and looking like you tried too hard, not to mention trying to pick the perfect spot for the date itself. Take a deep breath. Relax. It’s all going to be fine, as long as you’re yourself. But if you still need a little help, here’s our guide to what to wear on your first date back on the dating scene.

Dress to Show Off Your Personality

Maybe you finally got over a break-up and are ready to try again. Maybe your busy schedule has kept you from socializing for a while, but you’ve made it a priority to get back into dating. Whatever the reason that you’ve been off the scene, don’t worry. It’s just like riding a bike. Picking something to wear to try and impress your date can be more terrifying than the date itself. Our advice: show off your personality. Perhaps that means choosing a graphic t-shirt from your favorite concert. Or maybe it means dressing in sleek head-to-toe black. Be who you are, whatever that means for you. There are many ways to shine through your outfit choice on a date, and the most important one is to wear something that makes you feel like the best version of yourself. For some, that could be the shirt they’ve worn countless times, the one that’s perfectly worn in and soft to the touch. For others, it could mean going shopping for a new look, something they’ve been eyeing for a while and are super excited to whip out and show off. Now’s the time to invest in your wardrobe and in yourself.

Dress to Impress

You know that shirt that everyone always compliments you on when you wear it? For your first big date back on the scene, you may want to pull that one out. While you don’t need to get super fancy, it’s always nice to show that you care by putting in a little effort. This could mean wearing your nicest men's polo shirt with a cool pair of jeans and some sleek sneakers. Or maybe it means donning a nice V-neck sweater—you know, the one you wear to family events to look put together? That sweater might pair well with jeans or with a fresh pair of men's khakis pants, depending on the kind of spot you’ve chosen for the date. You also want to pick an outfit that fits you well. Ditch the slouchy jeans and sweatpants (do we really need to say this?) and slip on the jeans that fit you perfectly. Try tucking in a button-down oxford into your jeans with a nice leather belt and leather boots for a sleek but approachable look that’s sure to turn heads.

Dress for the Weather

Nothing is less cool than being too hot or too cold on your date. If your date is planned during the warmer months, layering is key. If you wear a sweater, make sure you have a t-shirt on underneath in case you end up sitting in the sun, in the park, or at an outdoor bar or café and need to lose the outer layer. You can layer a men's plaid shirt on top of a t-shirt as well, giving you options for fluctuating temperature in transitional times between seasons. If your date is happening when it’s colder out, bundle up! Perhaps your date begins with dinner. If it’s going well, it could lead to a second location, like a bar that’s a 15-minute walk away. You want to be prepared for whatever the night throws at you, and dressing warm is part of that. Make sure to check to see if there’s rain in the forecast. You’ll definitely score some points by bringing an umbrella, whether or not you need to share it.

Dress for Comfort

Nothing is more important on a date than feeling comfortable, both with who you are and how you feel. Part of what makes our favorite outfit our favorite is often how comfortable it is. If you bought a pair of new pants or a cool new shirt, but haven’t taken it out for a test spin yet, maybe hold off and save them for a later date. Maybe you have a pair of pants that look great but are a little tight around the waist. Pick something else. You don’t want anything to hold you back, and anything that pinches, prods, or bothers you in any way is going to be a distraction from the great date you’re having.

Getting back on the dating scene can be daunting at first, but having the right outfit is one way to step out there with confidence.


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