The 5 Baseball Cap Styles Every Guy Needs to Know

What's your go-to topper?

By Taylor Davies | Last Updated: Sep 8 2020

Aside from watches, there are few accessories men feel more impassioned about than hats.


Baseball cap styles.

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.

Keep scrolling for the 5 most popular baseball cap styles, and how to wear them:

#1 The Snapback

Most guys we know prefer this style of hat. 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.

Our favorite versions—and the ones most highly endorsed by the braintrust—rep cities, teams or a select brand like Nike, for example.

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?).

Shop #SGapproved snapbacks:

#2 The Fitted Cap

At SG HQ, we’re of the mindset that fitted caps are all about repping love. For a team, for a city, even for a well-loved brand. You can’t just pick a hat off the shelf because you like the color! That would be weird.

So 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 off chatter about this topic in the past, and the consensus is definitely, peel ’em. Now.

Shop #SGapproved fitted caps:

#3 The 5-Panel Hat

This hat is oh-so menswear. What started as a Brooklyn hipster-on-a-bicycle thing has become a surfer-hipster-city dweller-anyone-with-a-head thing.

So what’s the verdict? With the right outfit, we dig it.

We’d also add that this is probably the only style of hat that looks cool with an all-over print or pattern. 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.

Shop #SGapproved 5-panel caps:

#4 The Trucker Hat

Shop: Patagonia

We were tempted to go with a hard-and-fast “No” on this one, but we’ll give graces for a few select styles. The trucker hat draws up cringe-worthy flashbacks to the Ed Hardy days for many of us, and the truth is there’s not a ton of style appeal to this type of hat.

However, the mesh panel in the back does allow for a breathable, cooler fit, and perhaps in certain settings (Camping? On a boat? As a costume?) we could give the trucker a pass. Maybe.

Let’s just say: proceed with caution when it comes to trucker hats, and keep the occasion in mind.

Shop trucker hats:

#5 The “Dad Hat”

You know the kind of baseball cap style we’re talking about here. Made popular by the young folks in the early aughts thanks to Polo Ralph Lauren, these soft-style hats have become a kind of signature for dad-style and über-prepsters.

By this time, the dad hat has been around long enough for you to skip over any unintended connection to the dad-bod/dad-core phenomena.

If you want to wear one, opt for a logo-less cap in a unique hue or texture. And if you’re so inclined, apply the snapback logo trend to your soft-style hat.

Shop #SGapproved dad hats

No matter which type of cap you rock—it’s a personal preference, after all— there are a few guidelines to follow.

How to wear baseball cap styles with care:

  • Never wear a hat on a date.
  • Hats are for weekends, errands and ballgames, of course. Think of it this way: don’t wear a hat anywhere you wouldn’t wear a t-shirt. Meaning? They’re not for meeting your girlfriend’s parents the first time, on an interview, or to a place of worship. So wear wisely.
  • When it comes to sports teams, brands and logos…anything subtle and/or obscure get extra points. Think long-retired team colors, and vintage brand names.
  • Keep it clean—ladies rarely go for “grungy hat guy.”
  • Take the stickers off, you heathens! Seriously.
  • Most important? Be proud of the baseball cap styles you choose to wear. 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 final word on baseball cap styles…

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.


Ready to upgrade your style?

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.