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Hats are the unsung hero of a wardrobe. Not only do they protect your face from the sun and hide a bad coif, but they also make a statement in their own right. Just look at all the fuss caused by Loro Piana’s luxurious toppers on Succession: The show has been off the air for nearly a year and it is still inspiring would-be Kendall Roys everywhere. His fitted hat, also known as a baseball cap, from Loro Piana offered the right mix of sporty and stylish, becoming a core characteristic of the quiet luxury trend that overtook the fashion industry.
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Suffice it to say, Roy wasn’t the first billionaire—imaginary or otherwise—to wear a fitted hat on his private jet, but the attention Succession has brought to this distinct style has positively spurred a renaissance in the world of headwear. Myriad colors, patterns, and materials: There’s never been more fitted hats available.
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Personally, I love pairing a classic baseball cap with a wool overcoat—the tension between a refined Chesterfield with a seemingly unpretentious chapeau feels modern. It’s a combination that works for the office, as well as for happy hour with your colleagues. Basically, you’ll get a ton of mileage out of a good fitted hat.
If you’re new to the trend and are looking to partake in the fitted-hat revival, or are a card-carrying member of the cap club and are looking to add to your collection, we’ve rounded up the best options, styles that’ll have you looking like a billion bucks.
A Brief History of the Fitted Hat
The modern fitted hat draws its origins from the world of 19th-century baseball, when the Brooklyn Excelsiors used to wear caps with a long, rounded brim that featured a button on top. Over time, MLB teams began to emblazon their own distinctive logos on these toppers, eventually becoming coveted by fans who wanted to show their support. Then, in 1920, Ehrhardt Koch founded what became New Era, an American hat company headquartered in Buffalo, New York, that sold these styles to the masses. Flash forward to today, over a century later, and the label holds over 500 different licenses in its portfolio. It is the exclusive cap supplier for Major League Baseball.
Of course, the history of the fitted hat goes beyond just sport. Many pop-culture icons have turned baseball caps into fashion moments—from Mark Wahlberg to Princess Diana to hip-hop legends like Jay-Z. This style of hat has been seen on designer runways numerous times over the last decade at brands such as Burberry and Balenciaga. But it wasn’t until Loro Piana’s perfectly placed Succession cameo on Kendall Roy that a certain style of baseball cap truly became a symbol of luxury.
The Anatomy of a Fitted Hat
Fitted hats are typically sewn in six sections and topped with a fabric-covered button on the crown. They may or may not feature grommets or fabric eyelets for ventilation, and they tend to have a bit more stiffness than the more casual, athletically minded baseball chapeau. They also differ from traditional baseball caps in that fitted hats—as the name implies—come in various sizes to, well, fit the wearer’s head. Read: They aren’t usually built with an adjustable strap. But nowadays, fitted hats and baseball caps are interchangeable terms.
Best Original Fitted Hat
New Era Authentic Collection Low Profile 59FIFTY Fitted Hat
Buy Now on New Era Cap: $42
Here’s the alpha and omega of fitted hats, updated for today. Even if you’re not a Yankees fan—heck, even if you’re not a baseball fan—a New Era fitted Yankees cap is an enduring, timeless style statement. It features the embroidered logo of the Bronx Bombers, a classic six-panel construction, and a gently curved bill. It definitely pairs well with camel coats and private jets.
Date of Brand Origin: 1920.
Best Luxury Fitted Hat
Loro Piana Logo-Embroidered Storm System Cashmere-Felt Baseball Cap
Buy Now on Mr Porter: $525
The hat that launched a thousand lookalikes: If it’s good enough for Kendall Roy, it’s good enough for every man. Crafted from the brand’s luxurious Grade A Mongolian cashmere, it features a discrete tone-on-tone embroidered logo that whispers—never screams—luxury. And though the hat is made of cashmere, don’t assume that it’s delicate; it’s treated with the brand’s water-resistant and windproof “Storm System” technology. Because you never know what conditions will be like when you step off the company helicopter.
Date of Brand Origin: 1924.
Best Performance Fitted Hat
Varsity Headwear Active Tech Baseball Cap
Buy Now on Neiman Marcus: $95
The adjustable strap in the back makes this Varsity Headwear number categorically more of a baseball cap than a proper fitted hat, but the overall sleek silhouette and six-panel construction stays true to the fitted MO. Plus, it is made of a moisture-wicking, breathable tech fabric, allowing you to have the snuggest fit for your next jog.
Date of Brand Origin: 2013.
Best Sustainable Fitted Hat
Stone Island Econyl Regenerated Nylon Metal Hat
Buy Now on FWRD: $167
If eco-consciousness is something you value in your purchases, take a look at this Stone Island fitted hat. It’s made from Econyl recycled nylon fibers—the same luxe stuff that Prada uses in its Re-Nylon collection. Not to be outdone is the elasticized contour drawstring in the rear, which ensures that the hat won’t fall off as you run around town.
Date of Brand Origin: 1982.
Best Corduroy Fitted Hat
Brunello Cucinelli Cotton-Blend Corduroy Baseball Cap
Buy Now on Mr Porter: $650
Brunello Cucinelli, the king of cashmere, knows a thing or two about texture. If other quiet luxury hats are a little too, well, quiet for your taste, turn up the volume (slightly) with this textured corduroy cap. It’s made from a plush cotton-cashmere blend with just a hint of stretch for a reliable fit.
Date of Brand Origin: 1978.
Best Suede Fitted Hat
Paul Smith Suede Baseball Hat
Buy Now on Neiman Marcus: $175
Nothing exudes style quite like the fine texture of suede. Paul Smith offers his take on the fitted hat by making the six-panel construction in a supple, soft suede—finished with the brand’s signature multi-stripe adjustable band in the back.
Date of Brand Origin: 1970.
Best Cashmere Fitted Hat
The Row Caspian Cashmere Fitted Hat
Buy Now on Mytheresa: $690
Leave it to the Row to create something so quintessential, so luxurious that it makes even a baseball cap feel like an investment piece. This sleek style comes in a decadent midnight cashmere, with a curved brim and covered button.
Date of Brand Origin: 2006.
Best Textured Fitted Hat
Todd Snyder x New Era Red Sox Nubby Camel Cap
Buy Now on Todd Snyder: $98
We love Todd Snyder for his modern updates on all-American style—and this collaborative cap with New Era is no exception. It is made of a nubby camel hair fabric that looks just different enough to be visually interesting. But it’s still low-key enough that it won’t detract from the rest of your outfit.
Date of Brand Origin: 1920 (New Era), 2011 (Todd Snyder).
Best Drawstring Fitted Hat
Supreme x The North Face Trekking Soft Bill Camp Cap
Buy Now on Farfetch: $108
If you’re wearing your fitted hat for outdoor pursuits—trail running, hiking, kayaking, and so forth—you may appreciate the functional properties of this style. A collaboration between Supreme and the North Face, it’s made from a lightweight, water-resistant nylon, and features a drawstring fastening for the cozy fit. Rest assured, this one will keep you looking cool, feeling cool, and won’t go flying off at the first gust of wind.
Date of Brand Origin: 1994 (Supreme), 1966 (The North Face).
Best Wool Fitted Hat
Eton Wool Six-Panel Baseball Cap
Buy Now on Neiman Marcus: $215
If you know Eton for its signature shirts, you’re fully aware that the brand’s attention to detail and quality is fantastic—and this hat fits the bill. It’s made from a sturdy wool felt that’s perfect in colder weather, and it’s finished with a contrasting piped trim at the brim—a slight and cool flourish that we’ve come to expect from the label.
Date of Brand Origin: 1928.
Authors
Todd Plummer
Todd Plummer is a Boston-based style and travel writer. His work has appeared in the Wall Street Journal, Harper's Bazaar, New York Times, Vogue, W and more.
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