The Do's and Don'ts of Wearing a Baseball Cap

It’s baseball cap season. That’s true in the literal sense; the MLB is currently going strong and we’re not too far away from the All-Star Game in July. But it’s also a philosophical declaration. Because even if the idea of hitting a small white orb with a piece of wood and then running around a field were to disappear from the popular consciousness, it’d still be baseball cap season. It’s summer, baby! The sun is shining, the temperatures are soaring, and headwear that keeps the glare out of your eyes and the sweat off your brow is more essential than ever.

Of course, the prevalence of the baseball cap during the warmer months raises some questions. Should I be wearing one? What kind? Where? These are all valid queries, and the short answers, if you’re feeling impatient, are: sure, it depends, and it also depends. But you’re not here for the short version. You’re here to examine the nuances of the baseball cap in 2025 and figure out what works for you and when.

That’s where we come in. We’ll walk you through the key types of caps, a couple additional style considerations, and—crucially—when and where to wear yours. Let’s get into it.

Spike Lee, lover of caps.

This is the one we think of when we read the words baseball cap. It’s the quintessential accessory for America’s pastime. But unlike, say, the trench coat, the baseball cap didn’t arrive as a fully formed idea. Instead, it took most of the back half of the 19^th century and a good chunk of the 20^th to distill down into the design we know and love today. That design, which became popular in the ‘40s, features a stiff brim to block the sun and a soft cap with a higher, structured crown (often comprised of six panels) that’s perfect for displaying the logo of your favorite team. By the ‘50s, New Era—which has been the official supplier to Major League Baseball since 1993—arrived with the 59Fifty, still a part of the brand’s lineup and arguably the most iconic baseball cap of all time. These days, of course, you can find the design from a range of makers. Mitchell & Ness and Ebbets Field Flannels specialize in throwback designs, ’47 Brand offers a range of team logos and blank options, and sportswear juggernauts like Nike and Adidas are easy picks, too. You can opt for a fitted (as in, sized to your actual head) or get an adjustable version. You can also leave the brim flat or put in your own curve, depending on which brand you buy. These are entirely matters of choice. You do you.

Wear it with: Team gear (duh). Your favorite chino shorts (also duh). The goddamn coolest sneakers in your rotation right now (but consider not matching the color of the shoes to the hat). Streetwear-influenced fits that reach back to the early days for their inspiration.

Pharrell knows that dad hats can be high fashion.

The classic baseball cap can stand a little too tall or feel a little too structured for some guys. Enter: the dad hat. It utilizes the same core components as the classic baseball cap—stiff brim, six-panel cap—but softens things up for maximum casual vibes. The crown is shallower and unstructured, meaning there’s a little less real estate for huge team name—though that doesn’t stop folks from emblazoning that space with logos and graphics galore. It also sits a little more snugly on the top of your head and doesn’t ride as high. It’s a personal preference thing, but many guys who feel uncomfortable with the visual oomph of a baseball cap find the dad hat easier to wear. As far as makers go, the list is long. Like, impossibly long. Pretty much every merch collection—whether it’s from a megawatt musician or your local coffee shop—has a dad hat in the lineup. But if you’re looking for a few brands that specialize, check out Rowing Blazers, Corridor, and Todd Snyder for something special that’s not going to break the bank. If you want to invest? Well, there’s always Loro Piana, Brunello Cucinelli, or Zegna; all three luxury Italian labels make one hell of a dad hat, offering the style up in opulent materials like cashmere, linen, and ultrafine merino wool.

Wear it with: Baggier jeans and chinos. Preppy staples like oxford cloth button-downs and nubby sweaters (when the weather can accommodate the latter). New Balance 990s. Gramicci climbing pants, crinkly nylon shorts, boat shoes, and everything else that has a whiff of "father figure" but also looks freakin' great.

Ryan Gosling loves a trucker hat.

If it’s good enough for Gosling… The trucker hat was, for a good long while, consigned to 2000s-punchline status. It had earned its position, showing up with gaudy embellishments and aggressive artwork on some of the least likeable stars of the era. But after a couple of decades, it’s starting to feel fun again. The trick is treating the trucker—with its mesh paneling for breathability—more like you’d treat any other cap in your collection. Instead of going over-the-top and ironic, you can opt for an understated logo (or none at all). Leaning into a vintage vibe is a good idea, too. But instead of looking a mere two decades back, set your sights further. Channeling a bit of ‘70s or ‘80s inspiration for a logo, even a contemporary one, is rarely a bad idea. If you’d rather go for the real deal, you can find all sorts of great stuff from years past on eBay. And if you’d like to shop new, Western label Tecovas make a mean trucker, ’47 Brand has a whole collection of ‘em, and you can find versions from a ton of mass brands (like American Eagle and Urban Outfitters) with a younger customer base. Just don’t wear one if your jeans have bedazzled pockets (which the shouldn’t in the first place).

Wear it with: Bootcut jeans and slim denim jackets. Thrifted NASCAR tees and anything that has a Coors logo on it. Any and everything with a vintage feel, basically. On the other hand... Hyper-precisely cut suits, if you're Parisian and so cool that everyone's afraid to talk to you.

Now that you know the core styles, it’s time to dig into two key questions. The first is whether you want a blank cap or something with a logo or graphic. If your look is avowedly minimalist, then opting for something without even the slightest ornamentation is a good call. But don’t be afraid to have a little fun. Repping for your team is, of course, encouraged. But unless you’re a diehard fan or philosophically opposed to hat-based art, the best option in our book is a graphic of some sort. Maybe it’s a brand logo. Maybe it’s a picture of a skeleton or a dodo bird. Maybe it’s a location, a restaurant name, an in-joke. Just something to liven it up. Style can be serious business, but hats don’t have to.

The second question is whether to wear your hat backwards. Unless you’re JFK Jr. in the ‘90s, we wouldn’t advise it.

JFK Jr. makes this look good. You may not be so lucky.

The general rule of when to wear a baseball cap is very simple: the more casual the setting, the more likely a baseball cap will work. If you can see your toes, your calves, or the ocean, you can wear a baseball cap. If a large group of people is cheering for a group of men engaged in a ball-based competition, you can wear a baseball cap. If it’s the weekend and you’re doing your normal, off-the-clock routine, you can wear a baseball cap. If, on the other hand, it’s the weekend and you’re meeting your new partner’s parents for the first time, you may want to reconsider. Are they baseball cap people? Or are they brass-button blazer people? The answer may be a bit of both. You’ll need to calibrate your approach based on these nuances—and if in doubt, it’s better to ditch the cap. Same goes for the office, unless it’s a particularly chill dress code, and anywhere you’re required to wear a suit. That said, there are some notable exceptions, so let’s delve into a few potential scenarios.

Nic Cage proves that you can (and should!) wear a baseball cap while dodging paps at the airport.

…To the Office?

It’s probably best to take it off as you enter the building, especially if your company has anything approaching (or more formal than) the good ol’ “business casual” dress code. Baseball caps are all casual and no business.

Notable exceptions: You’re the CEO. You work in a creative office and you’ve seen at least two coworkers rock shorts this summer. You are employed by a baseball team.

…To the Game?

Of course! Wear it in good health, and go team!

Notable exception: Being the only guy at Yankee Stadium with a Boston hat on is counter indicated by most etiquette experts and medical professionals.

…To the Beach?

This is another no-brainer, my guy. Rock the hat and enjoy the sun-shielding benefits it provides.

Notable exception: If the beach has chairs that you pay for, a baffling amount of beautiful people, and a bunch of “private property” signs scattered about, you might want to opt for a seaside look that’s a bit more sophisticated. Big shades and SPF 75 are a good combo.

…To the Bar?

Depends on the bar. If there’s a game on, you’re good. If it’s still light outside, you’re also good. If the place serves $28 martinis and they’re brought to you by a man in a white dinner jacket, you are not good.

Notable exception: As with all things style, there are guys that can just plain pull it off—and that includes wearing a baseball cap while surrounded by folks in black tie. But you better be damn sure you’re one of them before giving it a go.