What to Wear to a Summer Date Night for Men

Summer is a great season for fun, casual date nights with someone special. But whether you’re taking a girl out for the first time or are going steady, you need to know what to wear so you look your best and give her the respect she deserves. Today, let’s break down what to wear to a summer date night for guys like you.

Keep it Classy and Comfortable

Above all else, remember this golden rule: you should try to keep things classy yet comfortable at the same time. That means:

  • Don’t wear a graphic T-shirt to a date
  • Don’t wear a tank top to a summer date
  • Don't wear swim trunks on a summer date

Instead, your summer date night outfit should indicate that you put some thought and effort into your appearance. That’s the best way to show that the date means something to you and that you want to look good for the person you are taking out to eat or to a show.

With that in mind, let’s take a look at some specific summer date night outfit ideas.

Button-Down with Jeans

You can’t go wrong with the menswear date night staple: a button-down shirt with nice jeans. This is a perfectly fine outfit for taking your date to a semi-casual or casual restaurant alike. A good button-down with jeans will show that you've cleaned up your appearance and want to look nice, without having to dress up all the way.

Button-Up Shirt with Chinos

Alternatively, you could opt for a button-up shirt with chinos. A button-up shirt in a light color like blue, beige, or a fun and summer-appropriate pattern is a great way to spice up your date night appearance and keep things light and fun. Chinos, meanwhile, are good alternatives to jeans, as they strike a perfect balance between casual and formal depending on the things you pair them with.

If you want to look fashionable and casual, pair your chinos and button-up with white sneakers. Vintage 1946 Stretch Twill pants could also be good partners with the button-up shirt of your choice.

Polo Shirt Plus Chinos

Polo shirts are also good summer date night choices. These basic yet classy shirts are best paired with chinos, preferably in a color like navy or dark gray. Wear matching white sneakers to complete your outfit. It's a great ensemble for taking an evening stroll, taking a date out for drinks, or going to a club.

Flannel, Undershirt, and Chinos

Some guys might opt for a flannel, plain undershirt, and chinos. A flannel is a solid choice if – depending on where you live – the summer nights can get a little chilly or breezy. Just make sure the undershirt, chinos, and flannel all color coordinate.

Your flannel and chinos should be complementary colors, for example, while you have a bit more freedom with your undershirt. Just make sure it isn’t a graphic T-shirt!

Linen Shirt with Chinos

A linen shirt with chinos – have you noticed a pattern with legwear yet? – is another stellar choice of a date night outfit for men. Linen is a comfortable, breathable fabric, so wearing a linen shirt will keep you cool and stylish at the same time while on your date night.

As before, pick stylish shoes that go with the rest of your articles to wrap up the outfit and look great.

Simple Tee with Nice Jeans (Sometimes)

Lastly, you can – in very limited circumstances – wear a simple T-shirt with nice jeans to a summer date night event. However, that T-shirt should be plain without any graphics. Your jeans should also be high-quality denim, not standard jeans you might wear to work or to do chores outside. Vintage 1946’s Negative Slub Pocket Crew Neck is a good example.

This outfit might work if your summer date night includes some type of outdoor activity or walking around, especially if you and your date might get a little dirty.


As you can see, you can wear a lot of different things depending on the formality level of your upcoming date, your personal preferences, and the outfit of your beau. Try to match her in terms of outfit formality, and you’ll be fine – that way, she won’t feel underdressed or overdressed when standing next to you and ordering food.

If you're not sure where to start your search for the best summer wear, Vintage 1946 can help. Check out our selection of shirts, shorts, and more today.