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Aside from watches, there are few accessories men feel more impassioned about than hats.
Specifically?
An SG follower once put it to us, “You’re either a hat guy, or you’re not.”
While this might be true—it’s not so simple. A quick poll of a few members of the SG braintrust (read: our guy friends) revealed that, for guys who give a lick about looking good, a well-chosen cap can go a long way.
For some, it’s a personal signature and weekend fixture. For others, baseball cap styles are an easy way to put a casual finishing touch on an otherwise more put-together look.
And then there are those who feel a baseball cap is only for keeping your hair out of your eyes while driving with the windows down and sunroof open.
Fair enough!
Practicality, personality, bald spots…the point is: there are a million reasons we love and fully support guys rocking baseball cap styles with panache and confidence.
When it comes to choosing your hat style, everything from team loyalty to coastal heritage can come into play. There are so many different types of hats for men and being familiar the different types of baseball caps is also critical so you can figure out which one suits you best.
A fitted cap is a brimmed hat has no closure in the back at all.
SG’s verdict: At SG HQ, we’re of the mindset that fitted caps are all about showing love. For a team, for a city, even for a well-loved brand.
That’s why our favorite versions—and the ones most highly endorsed by the fashion braintrust at large—rep cities, teams or even a brand (like Nike, for example).
The tl;dr? Don’t just pick a fitted cap off the shelf because you like the color! That would be weird. Instead, choose your allegiance and get the size right (oversized hats are not a thing).
Another note? Take the stickers off!
We’ve seen a lot of chatter about this topic in the past, and the consensus is definitely, peel ’em.
Dad hats are a little less structured than fitted caps, and have an adjustable closure (often metal or leather) in the back.
They’re usually super-simple, and often embroidered with silly or ironic images or slogans, rather than a sports team’s logo.
SG’s verdict: If you’re worried about looking out of touch or not in on the joke, don’t be. By now, the dad hat is ubiquitous and the style is too cool and comfortable to pass up.
It’s also great for guys who want to rock a hat but don’t want to rep a sports team on their headwear. We’d also rank dad hats among the best baseball hats for small heads because they’re designed to mimic the shape of your head; not too tight not too loose, and you can easily adjust them to fit without changing the overall aesthetic or shape.
Your best pick: You might have had a Polo Ralph Lauren version (you remember, with the polo horse?) back in the late 90s or early aughts. Since everything old is new again, you could go with that same style in 2021.
Otherwise, consider opting for something a little more offbeat.
A snapback hat is one where the adjustable closure in the back is made from plastic. You can make the hat larger or smaller by snapping the buttons on one side into the holes on the other. These along with dad caps are great options for twill baseball caps.
SG’s verdict: The snapback has been adopted within just about every “style camp” you can imagine, from streetwear to athleisure, preppy, hipster, California cool… We could go on.
Your best pick: On a practical note, dark color caps will go with most anything, and best hide signs of frequent wear (sweat on the inner band, anyone?).
A 5-panel cap is a hat with a more shallow crown, and often a flat bill. You can see in the picture above four of the five “panels” referred to in its name – one in front, two on the top, and one each on the side.
SG’s verdict: What started as an ’80s skater thing, then turned into a Brooklyn hipster-on-a-bicycle thing, has now become a surfer-hipster-city dweller-anyone-with-a-head thing.
Meaning? With the right outfit, we definitely dig it.
Lean into its skater roots by pairing it with workwear pants and a coach’s jacket. Or, keep things casual in joggers and a hoodie.
It’s also probably the only style of hat that looks cool with an all-over print or pattern.
Your best pick: In most cases, anything overly fussy or busy in design looks foolish, but not so with a 5-panel cap. So if you’re a fan of this style, seize the moment and get bold with pattern.
While a regular baseball cap is typically constructed of cotton, the sides of a trucker hat are plastic mesh while the front is made of a stiff foam.
One other critical difference in the great trucker hat vs. baseball hat debate is that trucker hats are also generally taller than most baseball caps.
SG’s verdict: I’ll be honest. We were tempted to go with a hard-and-fast “No” on this one.
The trucker hat draws up cringe-worthy flashbacks to the Ed Hardy days of the 2000’s, and the truth is there’s not a ton of style appeal to this type of hat.
However! The mesh paneling does allow for a breathable, cooler fit. Which means, in certain settings (Camping! On a boat!), we give the trucker a pass.
Your best pick: Let’s just say…proceed with caution when it comes to trucker hats, and keep the occasion in mind.
No matter which type of cap you rock—it’s a personal preference, after all— there are a few guidelines to follow.
The rules around wearing a baseball cap are changing. Hats used to be for weekends, errands and ballgames, of course.
Our advice used to be: don’t wear a hat anywhere you wouldn’t wear a t-shirt.
But that’s not true anymore!
If the men of Succession have taught us anything, it’s don’t go into business with family. If they’ve taught us two things? It’s that wearing a baseball cap with serious style is totally possible.
When it comes to wearing one with sports teams, brands and logos…anything subtle and/or obscure is best. Think long-retired team colors, and vintage brand names. It’s counterintuitive but the most trendy baseball hats for guys are actually the most classic.
Keep it clean—ladies rarely go for “grungy hat guy.”
Most important? Be proud of the baseball cap styles you choose to wear. Don’t stress too much about what you think might be a “cool” baseball cap and instead focus on the one that feels right for your day to day style. And remember, a cap doesn’t hide you.
On the contrary, it’s a huge indicator of your personal style, so embrace it and wear yours with confidence!
Wear it Well: Get creative with your outfit by juxtaposing floral shorts with a more rugged all-American baseball cap.
A linen henley is a great way to switch up your usual shirt routine, but keep in mind it may be quite thin and throw a white tee underneath. Round out the look by sliding on the most laid back of loafers with an espadrille feature.
A baseball cap is one of the best ways for a guy to instantly show something of his personality.
Women have tons of options for expressing themselves – skirts, dresses, weird culottes that you can’t tell if they’re shorts, or like…a romper, or something… Pile jewelry and accessories on top of that, and us ladies have about a trillion and two ways for her outfit to say, “This is who I am.”
Guys have – thankfully, or unfortunately, depending on how much you enjoy digging into your closet each morning – far fewer options to convey personality through their clothes.
So accessories play a bigger role.
A well-chosen baseball hat says a lot about a guy. Your chosen or inherited allegiances can be as much a part of your upbringing as Sunday dinners at your great aunt Melinda’s. Maybe more so.
That means, when a guy sports a baseball cap touting his beloved [insert team name here], it’s expressing a piece of himself the same way a woman might wear her grandmother’s wedding ring on a chain around her neck.
So what makes a great baseball cap? For starters, duration of ownership. Longer is better!
Think about it, your favorite hat is the one you’ve had since forever. Second, character. A great baseball cap’s brim is perfectly bent. Free of (visible) sweat rings, but bearing scuffs and fading from years of use – those marks show that your hat has seen you through a lot of life. And that’s a story we want to know more about.
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If you’re excited to invest in some new duds but dread the thought of shopping for them…consider having Team SG shop for you! We’re obviously biased, but we swear it’s really great!
Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are! If you’re ready for a style upgrade that’ll seriously improve your closet and your confidence, give us a shout.
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Baseball caps are, in many ways, the lazy option for headwear. They’re ubiquitous, they’re cheap and they go with everything. I completely understand those that fight the good fight for brimmed hats, and feel it necessary to attack ball caps in the process.
But a baseball cap can have an elegance to it, even with smarter clothing and tailoring. There are also good ones and bad ones, and people they suit more or less. So it’s likely worth writing some bits on PS - starting today with a personal piece on logos.
A baseball cap worn with fine clothing appeals (of course) because of the contrast. Here's a piece of sportswear being worn with something that is certainly not sportswear. One’s fine and sharp, the other (ideally) worn and battered. It’s a species of high/low dressing - which is always easiest with outerwear and accessories.
Though hasn’t this look been done to death? Haven’t Drake’s and related preppy brands, before them and since, made it trite? This is a question every reader has to answer for themselves, because it’s heavily dependent on their environs, their milieu.
Just keep in mind that you don’t live online. Despite the apparent prevalence of that style, I have yet to see a single person wearing it where I live in my little pocket of south London, and hardly anyone in Mayfair. Beware the perspective-distorting effects of the echo chamber.
There are levels of quality to a baseball cap, but as long as it’s 100% cotton (or leather, or wool - not a synthetic) it’s hard to go wrong. Even the little plastic adjustor on the back has some retro appeal, though personally I prefer cotton or leather.
However, I do think a cap is better with a logo, something personal.
A logo seems to look better to me because of the cap’s sportswear origins, and the fact so many of those have a prominent device. Without it, a baseball cap (not a military cap, or anything of that ilk) feels lacking.
A useful example is the growth of ‘luxury’ caps in recent years, particularly those that became a subject of discussion around the ‘stealth wealth’ of Succession.
To me, those caps, often from Loro Piana, feel rather lifeless. Like they’ve had the character and style sucked out of them. In the same way as cashmere denim, it's the result of someone trying to make a luxury version and removing its essence in the process.
My antipathy towards that type of cap is about the luxury material as well as the lack of logo, but they both feel symptomatic of the same neutered approach.
As to what a logo could be, my answer is anything meaningful.
You wear a band T-shirt to proclaim your passion for that band; you wear a football top to declare your loyalty to the team. I feel like a cap should be similar.
Mine tend to be souvenirs or brands I’m happy to represent. Ralph Lauren, Rubato, a red one from Holiday Boileau that reminds me of a nice day with the team in Paris - and which feels particularly significant given the shop no longer exists, and the whole 16th scene seems to be fading.
My favourite of course is my ‘Cal’ cap, from Berkeley in the US. I didn’t go, but it was a gift from a friend that did, so that feels OK. It still feels authentic.
It shouldn’t be a surprise that given all this, I’m not a big fan of the ironic logo, of a made-up club or team.
Wouldn’t it be cooler to actually wear the name of your local gardening club, where you volunteer on Sundays? Or the local tennis club? Perhaps the issue is people aren't members of such clubs any more.
Last June we took these shots in the Circolo del Tennis in Florence, which is the most wonderful place - old school style, baize tables and newspapers on sticks, kids running around in their white kit on the blazing clay courts.
The following week I was on Chiltern Street in London, and the back half of a shop had been taken over by an imagined tennis club, the Rochambeau. The idea was to promote a particular rosé wine - Racquet - that otherwise didn’t have a back story like other French wines.
It was all very clever, very well done - but it was really just another type of hype. After Florence, it felt a little hollow.
The one cap I have without a logo is from RRL which seems different because the rough-out suede is so rugged: it’s a whole outer layer on its own. Waxed caps feel similar.
Other exceptions include recreations of military caps that would never have had something on them, and of course actual vintage models.
Thinking about it, what I really want to push against is the prevalence of plain caps worn as just another piece of practical headwear, like a beanie (below). And perhaps the artificial distressed ones, which look so artificial. Just wear them and if you absolutely need to, sticking them in the washing machine a couple of times.
As with many rants, I’ve started with a feeling and rationalised my way through it. It’s cathartic. Hopefully some useful points rubbed off along the way.
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