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Menswear Essentials: Want To Build Your Hat Wardrobe? Start With These 10 Styles

The perfect pair of jeans. A flawless white dress shirt. A well-fitted navy suit. Black cap-toe oxfords. Air Jordans. There are just certain pieces that are key to building the perfect modern wardrobe. Oft overlooked, though, is the wardrobe that we put on our heads. Too many of us are happy wearing the logoed ball cap from some goodie bag or toss on a mascotted beanie left from college days. Just like clean, perfectly polished shoes, we will be judged by the way we top off our outfit.  Let’s do it with some care. Don’t get us wrong. We recognize that wearing hats can be daunting. We can’t all look like insouciant Instagram influencers whose every inch is curated, styled, and sponsored. But with a little practice, and by building up a foundation of hats that are easy-to-wear, soon we’ll be posing with the pros. Maybe best of all, by starting during the dog days of summer, we can not only practice looking good, we’ll also help protect ourselves from the sun’s damaging influence. 

The Baseball Cap

Southern Tide Thank A Trucker Performance Hat

It’s almost a given. A throwaway. Of course you have a baseball cap in your wardrobe. Don’t you? Derided by some, worn by many, this may be the most American of hats, MAGA notwithstanding. The trucker is the baseball cap’s country cousin. We can’t not talk about it. It’s the foundation of a man’s hat wardrobe. Find one with a message. Find one with performance. Find one with both: The Southern Tide “Thank a Trucker” not only broadcasts your appreciation for the essential service that America’s truckers have been providing — keeping us supplied with everything from toilet paper to masks to whatever else you’ve been ordering on Amazon this year — it also offers moisture-wicking, UPF protection, a performance sweatband for moisture management and padded comfort, and a Velcro adjustable fit. 

The Visor

Kühl Überkühl Visor

It’s barely a hat. It’s pretty much all brim. It’s not gonna offer you a lot in the way of sun-protection. So why bother? ‘Cause it’s cool, both literally and figuratively. Suddenly we’re moving from just throwing something on our heads to making a statement. A visor shades the eyes just so, while allowing the top of the head to be free in the breeze. It functions as an ersatz headband. It offers a bit of mid-century modern style. This one from Kühl is made from a quick-drying cotton-blend fabric that is also extremely lightweight. We like it with tennis shorts, but it’s also a great complement to track suits. 

The Bucket Hat

Obey X Dickies Bucket Hat

Obey X Dickies Bucket Hat

Inspired by WWII sailors, Gilligan’s Island, and the birth of hip-hop; the bucket hat moved from utilitarianism to iconic urban chic. It’s possible the perfect summer hat — easy to throw on, easy to roll-up into a back pocket—offering a slightly goofy but still cool attitude. This limited edition Obey collaboration from Dickies Life is reversible, offering Obey’s signature Andre The Giant motif on one side and a solid on the other. Wear it with camp shirts and jeans. Wear it with a suit. Wear it. Obey. 

The Cap

Tenth Street Moher Ivy Cap

Tenth Street Moher Ivy Cap

You know we’re fans of a good cap. The style offers a more grown-up take on the cap than most baseball caps; while offering a minimal, easy-to-wear silhouette. They are also available in a wide range of fabrics: Sure you’ll find everything from performance blends to comfortable cotton to authentic tweeds, but we like this leather version for its slightly vintage, slightly tough-guy stance. It’s perfect for throwing on for video conference calls when the hair’s not camera ready, and it’ll serve you well when fall’s cooler days set in. 

The Panama

Hampui Hats Atlantean Hills

Hampui Hats Atlantean Hills

It’s a misnomer. The classic Panama isn’t even from the South American isthmus. It’s actually from Ecuador. The classic white straw fedora was christened with the name when Teddy Roosevelt visited the construction of the Panama Canal and was photographed wearing the style. Since then it’s become a kind of standard for easy summer style with a bit of Hollywood flair. While classically rendered in white straw, we like this caramel-colored version from Hampui (be sure to check out their video about how Panamas are made) with its Shibori dyed band. It’s the perfect hat to keep on a hook next to the door. Throw it on for dinner out, a stop at the farmer’s market, or to mow the lawn with finesse. While it can finish a seersucker suit nicely, we like it tossed on with a simple t-shirt and chinos or shorts. 

The Lifeguard Hat

Sunday Afternoons Sun Guardian Hat

Sunday Afternoons Sun Guardian Hat

We’re just gonna say it and then apologize. Yes. Skin cancer is a thing. It’s very bad. That is no excuse for bad style. Yes, there is some one percent of the male population that can make those floppy canvas wide-brimmed sun hats look good. They are all male models. The rest of us look like dweebs. There. We said it and we’re sorry. (But not really.) Yes. There are those days when you are nowhere near a beach umbrella or shelter of any kind. You should be protecting your noggin, your face, your neck, and as much of you as possible. The lifeguard hat offers the kind of coverage that, well, a lifeguard needs, without the nerdy affect. This one from Sunday Afternoons offers even more protection with a UPF 50+brim and liner, and an elasticized headband for an awesome fit. 

The Cowboy Hat

Stetson Open Road 

Stetson Open Road 

Tread lightly here. There are places where only a true cowboy hat will work. Usually that’s where a true cowboy actually works. Maybe it’s a bar where a properly executed two-step is a rite of passage. The rest of us need a cowboy hat that can handle a family picnic or an outdoor concert. This hemp straw version from Stetson provides vintage-inspired style that feels classic and oddly modern.  Pair it with a crisp white linen shirt or a serape-blanket inspired pullover. 

The Fedora

Brixton Messer Fedora

Here is where we cross the line. The fedora is your introduction to the world of grown-up hats. A felt version provides a little welcome extra warmth as we head into fall. Once the uniform of Everyman, it both requires and instills a level of confidence. It can dress-up a pair of jeans and a t-shirt and lend Silver Screen credibility to a suit. Take your time. Wear it around the house. Get used to it. Then wear it everywhere with everything.  

The Knit Cap

Mack Weldon Tech Cashmere Hat

Mack Weldon Tech Cashmere Hat

From beanies to watch caps and beyond, the knit cap is the winter version of the baseball cap. If you don’t have one we’re just assuming you have a really thick head of hair and don’t live north of the Mason-Dixon Line. From rappers to skaters to baristas, it’s become a uniform of sorts; sometimes worn ironically, perched atop the head, over the ears where it’s little more than ornament; sometimes pulled down tight for braving arctic tundra, ski slopes, and windy city streets. We like them best when kept simple. Eschew graphics and pom-poms for neutral or bright colors (have a few of each!). We’re particularly partial to this cashmere/merino blend that not only feels soft against the scalp, but also holds its shape and keeps your head warm. Wear it with an oversized t-shirt or a puffy jacket, but this one even looks great with a classic overcoat. 

The Trapper

Nobis Nico Trapper Hat

In the 1950s hats with warming ear flaps were de rigeur for everyone from lumberjacks to rangers to sled-riding kids. By the end of the 20th century they’d been relegated to cartoonish characters embracing an Elmer Fudd sensibility. Today they are back, worn with more than just a little savoir faire; perhaps best worn when providing a kind of furry crown atop minimalist atonal silhouettes. We like this one from Nobis with a faux rascally rabbit lining. It’s a perfect way to round out your headwear wardrobe for winter’s coldest days while still maintaining your personal flair. 

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