What to Wear on a First Date (For Men)
Photo: themodestman

Nervous about what you’re going to wear on a first date? This article will help you choose the right outfit. First dates are nerve-wracking. Even guys who have been on a lot of first dates can still feel anxious about them.

Knowing what to wear on a first date is crucial to making a good first impression, and assembling a good outfit will take some planning. However, when the time comes for you to meet your date, you won’t be sweating trying to decide which crumpled shirt you should wear.

So let’s get to it. Here’s our practical guide on what to wear on a first date for guys.

It's All About the Fit

What matters most isn't how much money you spent on your clothes, but how well they fit on your body. The last thing you want is your date to be distracted by your loose and baggy getup. Typically, a fitted (but not skin-tight) silhouette—where your clothes hug but not constrict your body—is the way to go. Look for items like a tailored dinner jacket, straight-leg jeans or slim button-down shirt. It's all about wearing the clothes versus letting the clothes wear you.

Pay Attention to the Details

Sometimes it's the smallest things that get noticed, so before you leave the house, make sure every aspect of your look is on point. That means ironing out every last wrinkle crease, brushing away every last piece of lint, and leaving just the right amount of buttons open on your shirt—2-3 max. Not only will your date appreciate how put together you look, but you'll also feel much more confident yourself, according to menshealth.

Things to Consider

What to Wear on a First Date (For Men)
Photo: Internet

Before you even think about your clothes, you need to think about your actual date situation. There are many factors that can affect what you wear, and that’s where some planning will help.

Consider the Other Person

You don’t have to overhaul your personal style just for your date, but considering their tastes will likely come in handy. For example, if they tend to wear more casual, sporty clothing, then you might want to add a preppy touch to your outfit.

Dress Right for the Location

The actual place you’re meeting is going to have a huge effect on your outfit. You want to match the formality of the location (at least approximately) so that you don’t look out of place. If you’re meeting up at a bar and show up in a two-piece suit, things might get a little awkward, cites themodestman.

Think About Time of Day

This is another big factor. If your date is in the daytime, then you’ll probably want a more casual outfit. Generally, nighttime dates call for a slightly dressier look.

This ties into location. Daytime date locations (casual restaurants, coffee shops, parks, etc.) are typically more casual than nighttime locations (fancier restaurants, clubs, etc.). Of course, this isn’t a rule, so considering the location is still important.

Style DOs and DON'Ts

What to Wear on a First Date (For Men)
Photo: Pinterest

While every potential suitor has different tastes and preferences when it comes to style, there are certain rules to always keep in mind before stepping out the door.


  • Always, ALWAYS wear a watch: If there's one thing you should always wear on a first date, it's a nice watch. It doesn't have to be super expensive either — wear one with a metallic strap for a dressy dinner or opt for a sporty version for a casual daytime meet-up. Just having one on makes your whole look feel complete and put together.
  • Lean toward dark or neutral colors: Understated, muted colors keep your entire look grounded and sophisticated. Think navy, gray, white and black. It puts the focus on you and your conversation and not on what you're wearing. This applies to your jeans as well. Dark wash, always. That said, daytime dates are a bit more flexible in terms of color and washes. Feel free to have a little more fun then.
  • Wear quality underwear: If your first date ends up moving to the bedroom, you don't want to be that guy with the flimsy, stretched-out tighty-whities or cartoon boxers. A nice pair of neutral boxer briefs that fits perfectly will never steer you wrong. And even if the clothes never come off, the perfect pair allows you to focus on the date and not on any chafing or wedgies.
  • A little spritz of cologne: Smelling good is just as important as dressing right. A simple spray of your favorite scent (one inside your shirt and one outside, near your neck) is all you need to make a subtle impact. No need to go crazy with the cologne. You wouldn't want the smell to overpower the room.
  • Polish your shoes: Please don't overlook the importance of clean shoes. If you're wearing dress shoes, a quick black or brown polish is all it takes to make them look brand new. If you chose to wear sneakers, make sure all scuff marks and signs of wear are gone. Jason Markk makes the best shoe cleaning solution to help with that.


  • Hoodies: Leave the hoodies for, well, pretty much everywhere else except the first date. You want your date to know you put effort and thought into your outfit. If for someone reason you're meeting someone outdoors for a hangout in the cold, opt for a cashmere sweater and denim jacket instead. Layers show intent—hoodies are the opposite.
  • Open-toe shoes: No one wants to see your toenails—now matter how well-groomed they are—on a first date. Even if the date is super casual and takes place on a warm day, choose something like a driving loafer or moccasin instead.
  • Hats or sunglasses indoors: Don't let you date think you're trying to hide something right away. Keeping a hat on might make them think you're preoccupied with covering up hair loss. Sunglasses give a closed-off impression and wearing them indoors makes you not approachable.
    Ties: First dates should be about making everyone involved feel at ease. Ties can feel a littles stuffy and serious—and that's why it's okay to leave them at home. Even if you're meeting your date somewhere dressy, a simple tailored suit and dress shirt can do wonders.

    Busy Patterns: We're not saying your outfit has to be boring, but please leave the garish prints and crazy patterns at home. If you're trying to show off your whimsical and carefree personality through your clothes, start by incorporating smaller bits like a colorful pocket square or printed dress socks. Otherwise, stick with the foolproof neutral colors everywhere and let your humor speak for itself—not through your clothes.

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