What to Wear on a First Date - for Men

A first date is your chance to be your best you. You should aim to be smart and funny, charming and courteous, and of course you should look good. And that’s where we come in.

So where do we start when it comes to first date outfits? Here are some top tips to help you look your sharpest from top to toe.

Shirt or t-shirt?

This really depends on the location of the date. Are you meeting in a fancy restaurant? A cosy pub? Are you doing something active or are you going be sat in a darkened cinema?

A casual shirt is a good call for a first date, as you can dress it up with a blazer or dial it down with a denim or leather jacket. Check shirts look good all year round, while a natty patterned shirt might make more of a statement - if you’re that kind of guy. And if you’ve got a hot date in the summertime, short sleeve shirts offer another versatile option that you can build a look around.

Trousers or Jeans?

While jeans are acceptable in pretty much every scenario these days, perhaps cords or men's chinos will elevate you above the rest of the crowd. And they’re not too dressy for a night at your local tapas restaurant or favourite pub.


A well-chosen jacket can really hold together a first date outfit, so here are some classic options:

  • Blazer - A sharp blazer or suit jacket is a great way to complete a smart outfit or add a hint of stylish formality to jeans and a t-shirt.
  • Denim jacket - Whether you prefer raw indigo or stonewashed pale blue, a denim jacket is a great way to finish off a casual date outfit.
  • Leather jacket - A good leather jacket that matches the tones of the rest of your outfit can be a real statement piece. Think black biker jacket for blue jeans or a brown bomber for tan chinos.


And finally, we have the shoes. They complete your look and are as important as any other garment, so consider your footwear carefully. Your shoe colour doesn’t have to match the rest of your outfit, but they do have to go with it. A retro trainer might be smart enough for your date, but a classic brogue or stylish Chelsea boot is more likely to help you stand out as a man who has taste and isn’t afraid to use it!

There you have it. Follow these style tips as well as your own natural taste and you’re sure to be dressed to impress on your first date.