What Kinds of Shirts Best Match with Shorts?

So you think you’ve mastered shorts and have gathered a decent selection within your wardrobe. You’ve procured a few pairs that fit well, you’ve got a few different colors and pattern types, and now you’re ready for summer no matter what type of spontaneous occasion gets sprung on you.

Then, you realize something: “I have no idea what shirt to wear!”

Wearing most shirts with shorts isn’t exactly a do-or-die situation, but you’d be amazed at how many style points you can score when you properly pair the right shirt with the right pair of shorts. And since it’s summertime, it will be especially helpful to figure out which shirts stand the best chance at keeping you cool.


The oxford cloth button down style shirt should be an essential item in your wardrobe; it’s the shirt that can go with everything. It works well under a blazer and sweater in the winter, and it goes nicely with a pair of shorts during the summer. There is essentially nothing an oxford shirt can’t do, which makes it a worthy and essential item for your wardrobe.

Of course, a button-down shirt should be a solo top when you’re wearing them in summer, unless you have a pair of slacks to go along with your more ambitious outfits. It can be difficult to pull off the blazer-shorts combination; although, that’s not to say it’s never been done. If you consider yourself a beginner, it might be best to keep it a little conservative and stay away from experimenting with the more complicated ensembles.

Polo Shirts

Think of polo shirts as T-shirts dressed slightly up. A polo shirt is not only weather-appropriate, thanks to the short-sleeve options that polo’s are typically associated with, but having a collar always adds a new level of sharpness to your ensemble.

Matching a polo shirt to your shorts isn’t as hard as you might think. You can go with some classic, complementary colors--or you can buy a white polo shirt and watch it match with just about every pair of shorts in your wardrobe, including madras patterns.

Short-Sleeve Button Downs

A short-sleeve button down can be a nice, smart decision...if it fits right. There are few things that are as billowy and unflattering as an ill-fitting short-sleeve button down. Luckily, if you find a good fit, then matching it with your pair of shorts won’t be too difficult. If you’re wearing a short-sleeve button down with a pattern, it will help to wear a solid-colored pair of shorts to round out the outfit. Madras print and patterned shorts work well with solid-colored button downs because they provide a smart and simple contrast.


T-shirts are the ultimate casual item. There’s nothing wrong with having a well-fitting T-shirt in your wardrobe for when you want to relax with friends or enjoy a nice evening at home. But if your next social event calls for a little more fashion-forwardness, it will be important to remember that T-shirts are the quintessential casual item. That can be a good or a bad thing depending on where you’re heading next.

No matter what you wear this summer, you can always find a way to make it work. Keep an eye on complementary colors, patterns, and everything else that will factor into your next outfit, and you’re bound to look good and stay cool all summer long.