Dressing Up The Humble Baseball Cap


The baseball cap is often considered the realm of the uber-dressed down, even having a nickname of ‘dad hat’.

And it earned that nickname before dad style was considered cool by younger people.

Yet, there’s a great capability for baseball caps to be included in a variety of different looks for a hint of nonchalant flair.

You see, there’s plenty of different styles of classic hats. Flat caps, wide brimmed hats, fedoras, homburgs, boaters and so on… and so on. Most of them have a variety of looks that they fit with, but sometimes a classic or dressy hat just doesn’t feel right with an outfit.

Sometimes, something more casual is required. Especially for me, still being in my mid twenties there are some days where I don’t want to put a flat cap or dressier hat on with an outfit because it makes me feel artificially aged.

Now, plenty of people will have a bit of prejudice against the humble baseball cap. People who wear them regularly are often lumped in with a crowd generally deemed unstylish.

This doesn’t mean you can’t be stylish for wearing one.


Casual fits of all levels…

I’ve recently gravitated towards wearing a baseball cap with some dressy casual outfits, especially with Ivy-inspired styling.

Collegiate inspired style is a no-brainer for baseball caps, with varsity jackets and the like. Same with a denim jacket.

This is the kind of Ivy-inspired casual style that I think really works with a baseball cap. As simple as a tee, sport coat and light wash jeans.

I also wore a baseball cap with this outfit, but didn’t catch my face in the close up photo. I tried an overcoat with it too, but I think the coat may have been a touch too far on the formal end for the rest of the outfit. If I change the buttons on it to a brown, I think it should do better in a more dressed down context.

Some more casual tailored outfits I’ve worn a baseball cap with lately have included a linen overshirt with coral tailored pants, and a couple of softer tailored jackets.

Ring neck tees, casual layering and smart casual vibes like the far left are something I find suits a baseball cap better than a classic styled hat. This might just be because of my age – and perhaps my head shape – but that’s how it goes for me. Your mileage may vary!

I also like how the cap works with a rollneck sweater and soft tailoring as well, as shown by this post from The Anthology:

Come wintertime I’ll try a similar look to this. I’ll even have a similar pair of eyeglasses by then…


…and even with a tie?!

The next thing I want to experiment with are looks like these, which include plenty of layering and even a necktie.

Who would have thought a necktie and a baseball cap would look awesome together?

One of the best baseball cap and tailoring looks I’ve seen is this one below, which is Ivy to the bone in the best of ways:

The cap will even work with more formal suiting, if you layer it with an overcoat that bridges the gap. See below for two well done examples of this:

Another menswear guy I sometimes see baseball cap and tailoring looks from is Joe Laschet. I like his more casual approaches, like this one:

It’s a good way to appear youthful, I think; it gives off the appearance of a spring in the step. If you were to substitute the cap for a more classic hat, it would add age to the look. Now, this could be exactly what you want; if your vibe is that of a distinguished, mature man then by all means a classic hat will be an excellent choice.

But for someone like me, at 25, sometimes that just doesn’t feel right; and I’ll probably continue to experience that feeling from time to time for at least another decade.

But I digress.

Throwing on a baseball cap can add a dash of youthful sprezz to a look, and I think there’s a cerrain appeal to that. It would be easy to write it off and call it immature by classical standards, but that’s a matter of personal taste.

I like this look, and I look forward to continuing my experiments with it.


Conclusion: a fun way to add a spark of difference.

The baseball cap isn’t necessarily a mark of the unstylish. In considered hands, it can be a mark of fun and youthful spark.

Have you ever tried an outfit like this? How did it look?


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Sam founded STS in 2019 to help his fellow man not just to dress (and smell) fantastic, but to enjoy it too. An avid motorcyclist, musician and sportsman, he spends most of his spare time in those pursuits.

3 thoughts on “Dressing Up The Humble Baseball Cap

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