Five Ways to Make Shorts Work on the First Date

Summer is the perfect time to meet new people and, yes, go on first dates. But we know it’s hot out there. And while you want to look good, part of you knows that it’s more important to stay comfortable and sweat-free.

How do you strike the balance between giving your first date the right impression while wearing a pair of shorts? Here are a few simple tips.

Buy quality shorts.

A quality pair of Sahara Twill Flat Front Shorts is going to be far more appropriate for the restaurant than, say, your gym shorts.

It all starts with shorts selection: do you have an eye for what makes one pair of shorts more occasion-appropriate than the next pair? If not, then stick to these simple rules:

  • Avoid cargo pockets. Sure, you can pull them off, but it’s easier to keep it basic.
  • Go with a conservative color. Khaki, salmon, light blue—there are plenty of options for your first pair of high-quality shorts.

Wear a shirt with a collar.

We know this is a first date and not a first anniversary date. But it’s still important to remember that you have to look like you’re making an effort here. Shorts will keep things casual, but the top you wear will say a lot about just how seriously you’re taking this first meeting. Our rule of thumb: find a shirt with a collar.

Your two basic options here are polos and button downs. Polos are a little more casual than first date material, so when in doubt, go with the button down. If it’s too warm outside, you can always roll the sleeves up.

Go sockless.

It takes a bold man to pull off shorts with socks these days, and let’s face it: on a first date, it’s better that your bold personality shine through than your bold style choices. It’s safer to go sockless and stick to a simple pair of boat shoes or even canvas shoes. If you don’t like how going sockless feels, then “no-show” socks might be a great option for you.

Keep the accessories to a minimum.

When you’re wearing shorts, your casual look lends itself to a couple of accessories—maybe a bracelet or a watch. Unless you always go with a lot of accessories as part of your usual routine and you’ve got your style down to a science, it’s probably best to stick to one or two items at most. Keep it simple.

Don’t wear a hat.

We know these tips sound conservative, but keep in mind that pulling off shorts on a first date is fraught with challenges. You can wear a hat if you wish, of course, but it’s far safer for a first impression to opt against it and simply present yourself in the simplest, most modern way possible. You want to communicate that you’re a date-able gentleman who knows how to dress himself. A cap with your favorite sports team may go against that image. Best of luck!