If you’ve spent any significant amount of time within the online men’s style space, be it on Instagram, TikTok, or even Pinterest, you’ve likely come across a massive uptick in recent years of something that, at first glance, appears to be an unlikely pairing.
Well-dressed fellas rocking rich, textured tweed or even sleek, classy suits…and a baseball cap, sometimes bearing the logo of a favorite sports team, Alma Mater, or something else entirely, perched atop their heads.
To those less familiar with this trend, it may appear to be quite the strange juxtaposition. In our increasingly casual world, wearing any form of tailoring tends to read as slightly formal for most occasions, or at the very least, “dressed up a bit.”
However, baseball caps have remained, for the most part, as a firmly casual piece of headwear. Many observing this phenomenon might struggle to see the vision. The two seem a bit at odds with each other, after all.
So what’s the deal with this trend of mixing these two worlds of style? What is the intended outcome? Is the aesthetic grounded in some sort of lesser-known historical context? Or is it truly a new hybrid look?
And regardless of whether or not it has a precedent, the top question on many men’s minds is – is wearing baseball caps with tailored clothing a style success, or sacrilege?
A Brief History of the Ball Cap
The very first iterations of the now ubiquitous baseball cap, also referred to as a “ball cap,” can be traced to the 1860s, when the Brooklyn Excelsiors, an amateur baseball team sported a rough version of the hat which slowly took on other forms as it spread in popularity.
The six-panelled, round-domed, and curved-peak version we know today emerged in the 1880s, and in 1901, the Detroit Tigers were the first to add their mascot, a red tiger, to the front of the hat.
These hats were tremendously popular among baseball players during this period, and of course, they have remained a standard part of the baseball uniform even today, albeit with some modern design changes and updates.
Simply, Sportswear
At the end of the day, a ball cap owes its origins to a form of sport. Even though today, many simply wear them out and about regardless of what they’re doing, baseball caps have a sporty connotation.
So, it may surprise you when we bring up the fact that the earliest suits were also, in many ways, a sporting garment. The suit as we know it today owes much of its heritage to the “lounge suits” of mid nineteenth century Britain, which were suits made from more rugged materials like tweed and intended for hunting and outdoor sporting.
These were a departure from the more formal frock coats seen in British cities and town centers, with shorter jackets and an emphasis on causal materials.
Eventually, the cut of the lounge suit made its way into more formal spaces, leading to the worsted wool suits we know today.
But one mustn't dismiss the fact that, despite being a sign of formality today, the first suits were not only casual – they were sportswear!
And so, the marriage between a humble baseball cap and a modern suit might begin to make more sense once you look at it through this combined historical context. As it turns out, they’re not so disconnected after all! Quite the contrary, in fact.
Today’s Trendsetters
Arguably the most prolific forces in favor of the ball cap + suit combination are luxury menswear brands such as Drake’s of London and Aimé Leon Dore. Both brands, among others, have significant cult followings that influence a number of trends in the modern menswear landscape.
Their lookbooks, however, for many years now, have featured a lot of ball caps and tailored garments styled together in harmony. And as a result, stylish fellas everywhere have taken note.
You may be seeing the trend on your TikTok FYP, Instagram Feed, or even out and about on the street. Those who pull it off best are likely highly attuned to the origins of their tailoring, which can result in a better look overall.
There’s no shame in experimentation though, so anyone who is attempting to try out a fun, new style is doing good in our book.
But you may not be interested in simply “experimenting.” You want to try the look out for yourself and totally crush it! Well, the good news is, you absolutely can. And we can help.
How to Wear A Baseball Cap with Tailoring Well
Level – Beginner:
If you’re feeling less fashion-forward, we recommend that you start with a very casual piece of tailoring to ease into the trend. So, you can opt for a tweed, corduroy, cotton, or linen sport coat, to start.
Pair it with your favorite jeans or chinos, some simple sneakers, loafers, or derbies, and an oxford cloth button down shirt.
Great! You have the basis for a perfect, smart-casual ensemble. Now, just to add the hat.
For maximum authenticity, it helps to wear a baseball cap that bears the emblem of your favorite team – but of course, not all ball caps are sports merch, so any old hat with a design or branding you appreciate will work.
Love a particular beer? They probably have a hat for you to wear – practically guaranteed.
Or maybe you have a favorite city, national park, or country you enjoy visiting.
Whatever it is that you fancy, you can rock it with pride on your head. Just make sure it fits you!
Level – Intermediate
Adding a ball cap to the previously described ensemble is pretty damn easy, and we recommend you start there. But if you’re interested in a more advances technique, you can swap out the sport coat for a full suit – just keep it to something made from a fairly casual fabric to stay on track.
Like the last example, a suit made from tweed, corduroy, cotton, linen, and even seersucker is a good bet. The casualness of the suit will be matched to the ball cap – so long as you style everything else with precision.
Again, an oxford cloth button down shirt is your best friend, but you can often rock a denim western shirt or even a long sleeve polo sweater instead. Casual shoes like penny loafers, derbies, or simple sneakers are still recommended, as well.
If you want to take it up another notch, consider a tie. A knit tie will likely pair the easiest, but more elaborate silky varieties can work too with a well-trained eye.
Level – Expert
If you’re ready to try out this trend at its most extreme, you’ve got to keep a number of things under consideration. The most formal suits beyond, well, a straight-up tuxedo, are smooth, worsted wool varieties in darker colors.
Navy blue, charcoal gray, etc. Pinstripes and other classic patterns may apply here as well.
These can be worn with ball caps to show off the most delicate end of this trend, but it can be a bit tricky.
This may sound counter-intuitive, but arguably the best way to combine a more formal suit with a ball cap is by dressing down the suit itself to the best of your ability.
Try pairing it with a plain white tee, tucked in, or perhaps a western shirt (with cowboy boots to match) to create an interesting juxtaposition between differing aesthetics.
It has to look intentional, not oblivious. A demonstration that you understand these aesthetics so well, that you can bring them together in new and unexpected ways.
This is somewhat of a styling philosophy of the highly-esteemed Ralph Lauren himself, who has often been known to create these types of interesting juxtapositions in fashion.
Only once you successfully take the formal suit down a notch, will a ball cap look appropriate as an overall look. Otherwise, it’ll simply appear as if you don’t know what you’re doing.
This method takes time and a highly-trained eye, but with patience and perseverance you can definitely pull it off!
The Verdict
We can’t knock a trend that allows fellas to experiment with their style in creative ways.
While to many, a baseball cap and a tailored garment are always going to look strange together, there is a fair bit of precedent to back it up, as well as a number of ways to do it in a fool-proof manner.
We recommend you give it a try, and see if it’s for you! Chances are, you’ve already got the pieces to get started. So, put ‘em on, and see how you feel!
In our book, this trend is here to stay – and heck, it’s likely only going to become more popular as other men’s fashion brands, especially in the contemporary space, continue to push it.
So, have fun with it, and happy dressin’! We’re sure your attempt will be a total grand slam!
