The classic symbol of American weekend and leisure wear…but make it fashion. A baseball cap isn’t the first thing one chooses to spend a small fortune on, as it’s usually the final addition to an outfit, more for function than form. Most Americans grow up wearing them, but their place as a part of a polished look is more recent. I almost always wear a cap to the gym (part of my “exercise uniform”) but also reach for one whenever my hair isn’t looking its effortless best and I don’t plan to shower before I get dressed. Fashion baseball caps are the natural evolution of the shape, in step with athleisure’s prominence as an acceptable look in almost any context, and the blending of classic streetwear with conventional luxury. In other words, when brands like Hermès are making sneakers and track jackets, the humble baseball cap is no stretch.
And why not spend a bit more for something you wear often, are seen and perhaps photographed in, and which also serves a functional purpose (concealing messy hair and blocking the sun’s damaging rays)? I’ve worn the same two Lululemon caps for over a year, and feel the time is right to consider an upgrade. I’ve assembled some of my favorite fashion baseball caps here for your (and my) consideration:
Marni logo-embroidered baseball cap

Marni logo embroidered fashion baseball cap in olive
Bold, abstract, and with a nod to fashion, for those familiar with Marni, without shouting it. I love the color-blocked logo on the bill. $350 at Farfetch for olive or white and $375 at Matchesfashion for navy blue.
Drôle de Monsieur NFPM baseball cap

Drôle de Monsieur “Not from Paris Madame” baseball cap in black and olive
This one made me chuckle, and sometimes it’s fun to have a laugh and be a bit cheeky with accessories. Not from Paris Madame is subtle enough to only attract bits of attention here and there. The white on black is crisp. $90 at Luisaviaroma for black or 65€ at Drôle’s website for other colors.
Acne Studios corduroy baseball cap

Acne Studios Carliy corduroy baseball cap
It is fall now, technically, and corduroy is a great fall fabric. It’s warm, textural, and in this iteration, comes in a bright turquoise hue (as well as navy blue). Acne is great at making interesting things but upending them slightly. Notice that the “Studios” is upside down and backward. $110 at WANT Apothecary.
Etro Star Wars logo cap

Etro Star Wars capsule collection baseball cap
Part of a capsule collection to celebrate the newest installment of the franchise (The Rise of Skywalker), this baseball cap is an odd collision of cultures. But, nothing feels off the table anymore, so I guess it shouldn’t be such a surprise. At least it’s different, unexpected, and perhaps also a bit geeky-chic? $208 at Farfetch.
Alexander McQueen embroidered-logo baseball cap

Alexander McQueen red on black script logo baseball cap
I like this one simply because it’s a bold color combination—reminds me a bit of “Netflix” or “Stranger Things”—but it also only says “McQueen”, which leaves a bit of mystery and ambiguity rather than fully stating “Alexander McQueen.” The script used is also nice looking. $330 at Matchesfashion.
Prada nylon logo-embroidered cap

Prada embroidered-logo nylon baseball cap
This one is perhaps the most obnoxious of the selection. Though it’s ostentatious, I like it, perhaps because the black embroidery on an olive background is just quiet enough (rather than something with more contrast). Or it’s the use of the full House of Savoy coat of arms and rope in the logo, the totality of which was created when Prada became an official supplier to the Italian royal family in 1919. I think it’s classier than Prada slapping its enamel triangle logo plaque on everything, including baseball caps. $270 at Matchesfashion.
Burberry Monogram Motif baseball cap

Burberry Monogram Motif logo baseball hat
As a nod to traditional baseball caps that sport embroidered two letter team monogram logos (like “SF” for the San Francisco Giants or “NY” for the New York Yankees), Burberry’s “TB” monogram logo stands for Thomas Burberry and appears in a contrasting white on black, which from afar appears like a baseball team cap. Thomas Burberry founded his eponymous apparel company in 1856 in Basingstoke, England (50 miles from London) under the guiding principle that clothing should be designed to “protect people from the British weather.” So while today’s Burberry is a wholly different sort of brand than it was 163 years ago, a baseball cap from the house actually fits its heritage quite well. $260 at Burberry.
Loro Piana Wind Logo baseball cap

Loro Piana wind logo baseball cap
This last one is perhaps the bougiest of all, if only because it is so stealth, so old money, and is fittingly not the most expensive in the lot. [Sidebar: legend goes that of all Mercedes-Benz drivers, the wealthiest are those who choose the E-class station wagon, not the more expensive, flashy models like the S or SL. And certainly they don’t bother with any of the brand’s SUVs.]
Anyway, Loro Piana has made sport look ultra luxurious for years (and vice-versa, luxury look sporty). This hat is no different, and looks equally perfect for cruising Rodeo Drive or sailing on the Adriatic. Since it’s nylon, I’d imagine it’s also durable enough to withstand some sea spray. $275 at Barneys.
I have tried many baseball caps in my life, and most of them don’t fit my extra large head. But with these new fashion baseball caps in intriguing colors and motifs, several of them in XL size, I plan to invest in one soon.
For more style posts, click here. To look at other Fall 2019 menswear, click here.