How To Style A Baseball Hat

I think you're either a hat person, or you're not, but with Highr wide range of styles, you might just find yourself wearing some hats and not others—or wearing them all, or none at all.

Are You A Baseball Hat Person?

I’ve always envied people who can pull off a hat, especially a baseball hat. I never even thought to try one on myself because I instantly felt silly whenever I did—whether it was for a quick attempt or the few times I threw one on just to see.

Remember those Von Dutch trucker hats we all wanted in the early 2000s, thanks to Paris Hilton? I think that trend may have scarred me a little, making me hesitant to revisit the world of caps.

But then comes spring and summer, and a good warm-weather vacation, and suddenly I’m all in on a wide-brim straw fedora. I love wearing them, and they make me feel pretty—but that’s pretty much where it ends.

I even tried the wide-brim felt hat for fall and winter, channeling that ultimate blogger "it girl" vibe back in the mid-2010s. I think those might be retired now (hopefully). But you know what? The Millennial twist on that may just be a cool baseball hat—maybe I’ve found my new style after all!

How To Style A Baseball Hat

I’m still figuring out how to style a baseball hat, but I’m quickly learning what works for me and what doesn’t. Here are a few style tips I’m embracing when it comes to incorporating a baseball cap into my personal style.

Choose A Color That Contrasts With Your Hair

I think this is part of why I’ve been hesitant to wear hats in the past. Many I tried were always black, brown, or some other dark color, and I just didn’t love how it looked against my dark hair. But when I tried on this green hat from Highr, I loved how it contrasted with my hair and brought a fresh pop to my look.

Juxtapose the Menswear-Inspired Accessory

Maybe it's just me, but I’ve always felt that baseball hats have a more menswear-inspired vibe. Because of that, I love contrasting them with more feminine pieces when I can. Of course, not always—like in today’s look, where I’ve paired a baseball hat with jeans, a tee, and a blazer for a bit of an androgynous feel.

But I really love the contrast of a baseball hat with a more feminine dress to add some edge to the look. However, there’s a fine line to walk. Baseball hats are casual, so I wouldn’t pair them with something too formal like a fancy floral dress. A good rule of thumb is if you can wear the dress with sneakers, it’ll likely work with a baseball hat too.

At the same time, I think some street-style looks, like the one I'm wearing today with jeans and a blazer, can be easily elevated by adding a cool heel or boot. It’s all about playing around with accessories to find the perfect balance.

Complete Your Look

Baseball hats can sometimes feel super casual, like the thing you throw on to cover up your messy hair when you're running out the door in sweats. And while I’m all for that laid-back vibe, you can elevate even that look by completing your outfit. If you’re aiming to make a fashion statement with your hat, I recommend finishing the look with a few key details.

Just like I always say you can rock sweatpants in public and still look polished or wear a matching set that feels like pajamas but make it chic, the same principle applies to styling a baseball hat.

To elevate your outfit, add the finishing touches—think jewelry, a bold lip, and swapping your everyday work tote for a stylish bag. These small additions really help make your look feel more cohesive and put-together.