Do Baseball Caps Have A Place In A Man’s Wardrobe?

I have done a couple of these articles in the past (here and here) and today I want to discuss baseball caps.

Baseball caps are pretty divisive in the world of menswear.

In one camp, you have the folks who say that baseball caps are infantile and anyone who wears them looks like an early-2000s frat bro or an extra in a Limp Bizkit video.

In the other camp, you have the folks who wear baseball caps with everything from casual streetwear to finely tailored suits, the latter combination demonstrating how “in-the-know” they are when it comes to hashtag-menswear since they are bending conventional style rules. You better believe that suit-and-cap combo is ending up on Instagram!

When you get into classic menswear and really begin caring about your appearance, you may think you need to align with one of those two perspectives. But I don’t believe that’s true.

My view on baseball caps falls somewhere in the middle of those two viewpoints.

Is there a place in a man’s wardrobe for a baseball cap or two? Absolutely. But, like with everything else, there are optimal ways in which to utilize them from stylistic and practical standpoints.

Here is the most important thing to keep in mind when styling a baseball cap…

Don’t get cute.

By that, I mean don’t try to “make it work” with other wardrobe pieces that clash with the baseball cap’s informality. What I am saying is that I disagree with people who wear their caps with tailoring.

Baseball caps, like ripped jeans or shorts, are ultra-casual. That isn’t a knock against how they look. There are plenty of ultra-casual items (leather jackets, heavy boots) that are incredible looking. But we don’t fool ourselves into thinking they are anything but ultra-casual.

They look good but only when they stick to their very specific place on the Formality Spectrum.

And there is nothing wrong with that!

But when you take a really casual piece and intentionally combine it with much more formal pieces, the end result is jarring. If you wear a baseball cap with a suit or sport coat, you’re drawing WAY too much attention to the cap. People won’t focus on YOU… they’ll focus on what you’re wearing, which isn’t the goal.

If you’re dressing well and are truly stylish, then what you wear won’t be seen on you.

The problem with wearing a baseball cap with more formal clothing is that the wearing of the cap was a choice. There are so many better alternatives for headwear when you’re wearing tailoring.

A newsboy or flat cap. A brimmed hat like a fedora or Panama hat. Heck, even a wool beanie or watch hat looks better than a baseball cap, provided the tailoring you’re wearing at the time is rougher and more utilitarian like a tweed jacket.

Wearing a baseball cap with tailoring gives off major “How do you do, fellow kids?” vibes.

It reminds me of those unsufferable C-suite executives who pop on their baseball caps at 5:00pm to show how “relaxed” and “fun” they are before heading to some midtown wine bar and berating the waitstaff.

So, from an “outfit” perspective, make sure you reserve the baseball caps for strictly casual wear.

But even when worn casually (which is the correct way to wear them), not all baseball caps are created equal. Some look better than others.

In my opinion, baseball caps looks best when they are relatively dark and minimalistic. Or if they represent some sort of personal attachment. This is what I mean…

Obviously, baseball caps usually depict sports teams. Unfortunately, many sports teams have really garish, unattractive colors. Try to stay away from those if you care about looking good in your baseball cap.

Off the top of my head, the teams that have best looking caps are the Yankees, Red Sox, and Tigers. Their hats are dark and the logos are simple.

If you’re not repping a team, then make sure your cap has some sort of personal attachment. I have a couple caps that are from local fairs or vacation spots or breweries I like. Each cap is from a place I have been with which I have a connection.

It’s important to remember to NOT wear the cap backwards, though. You’re a grown man and wearing a cap backwards IS an infantile look. The only times you should turn your hat around is if the situation genuinely calls for it. If you’re donning a catcher’s mask or shooting a basketball or using a bow-and-arrow or something like that, then yes, it’s ok to turn your hat around since the brim would get in the way otherwise. But outside of instances like those, just keep your hat on properly so you don’t look like you’re in Kris Kross.

Now that we have discussed the stylistic aspect of baseball caps, let’s talk about them from a practicality perspective.

I’ve written before about how baseball caps are good for specific activities… like playing baseball (duh) or any other outdoor physical pursuit like running, given their snug fit and long front brim.

They are also excellent for a “grab-and-go” piece of headwear, provided you’re dressed casually. Maybe some days you don’t want to give much thought to what you’re wearing and honestly, in this day and age, no one will bat an eye if you’re wearing a baseball cap. Basically, baseball caps are great if you want anonymity for the day.

My one gripe about baseball caps (and the reason I don’t wear them much) is because they don’t provide much weather or sun protection. Sure, the front brim protects my face, but what about the back of my neck or my ears? I don’t want a sunburn and I certainly don’t want rain or snow going down my collar. That’s why I usually wear newsboy caps or wide-brimmed hats like Stetsons.

But doesn’t a baseball cap provide the same level of protection as a newsboy or flat cap?

Not really.

I find the puffiness and thick wool of those caps provide more of a barrier to precipitation than the thinner material of a baseball cap.

The best baseball caps for overall protection are the ones that are 100% wool.

I’ve never understood trucker caps, though. I get that someone might want the coolness and airflow that the mesh back allows, but doesn’t that make it so that the hat doesn’t provide any sun or weather protection at all? What’s the point of the hat then? Maybe someone can enlighten me.

Now, the $64,000 question: Do I wear baseball caps?

Yes! I am wearing one today, actually! It’s a grey cap with a leather patch from a brewery in the upstate New York town I used to live in. Wearing the cap reminds me of those days and the time I visited that brewery with good friends.

The cap is dark, minimalistic, and has a deep personal connection. The rest of my outfit consists of a flannel shirt, jeans, and boots so I’m wearing the cap pretty much as casually as possible.

So, there you have it. Yes, there is definitely a place in a man’s wardrobe for a baseball cap, provided it’s worn in the proper context.

And PLEASE take the damn sticker off the brim before you wear it out in public!