Four Tips for Matching Shirts and Shorts

You have great shorts. You have great shirts. But putting them together might not always feel as easy as it should. Fortunately, there are a few tried-and-true rules you can stick to if you want the best pairings to make great cool-weather outfits. Here are our favorite tips for matching shirts and shorts.

Select a Color Scheme First

When you flip through hangers in your closet, the first thing on your mind should be simple: color. Matching colors the right way will handle most of the work for you. Here are some safe color options to stick with as you learn:

• White: White pairs with just about anything. A white shirt will pair with khaki, navy, red—even exotic madras patterns and prints.
• Blue and Red: There’s a reason many of the world’s flags contain both colors. They simply work together.
• Light and Dark: A lighter pastel color like yellow can often pair well with a darker, bolder color such as navy.
• Pale Parings: If you want something bolder in your color combinations, like sage green with yellow, try to keep both colors on the lighter side to avoid an overwhelming look.

Over time, you’ll get the hang of which combinations work for matching shirts and shorts and which don’t. Then, you can go to the next level.

Try Some Contrast

If you feel uncomfortable wearing a pale blue shirt over dark blue shorts, there’s a reason for that: your outfit doesn’t have enough contrast, and you know it. Because white is a light color that contrasts with and complements other colors, it works well in almost any short-shirt pairing. But you don’t always want to rely on white, either.

To experiment with new pairings, bring your shorts to the closet and hold them up to your shirts. See if anything strikes you that you might not have noticed otherwise. And remember: contrast is a good thing, but too much of it risks going into “clash” territory.

Dress to the Situation

The old saying that a mullet haircut is “business in the front and party in the back” is a good example of what not to do when matching shirts and shorts. A blazer and tie over a pair of shorts isn’t a formal outfit—it simply looks like you didn’t know where you were headed.

Dress to the situation by pairing the shorts and the shirt with relative similarity. A simple button down dress shirt can dress “up” a casual pair of shorts, but go any more formal than that for the top and you’re bound to clash.

Try Something New on a Regular Basis

Finally, you’ll never learn anything if you don’t actually try some of these tips out in the real world. Trying something new can be a little scary and even uncomfortable. But the more you expand your sense of fashion, the sooner you’ll find the combinations that really work for your individual sense of style.

Shop Vintage 1946

And don’t forget to start by browsing all of our vintage shorts styles—you never know which one will catch your eye.