Since the brand opened its doors in 1994, the five-panel camp cap has played a pivotal role in the [Supreme] legacy. Nearly as iconic as the label’s hallmark Box Logo T-shirt, for more than 25 years, skaters, punks, and downtown kids galore have rocked the paneled camp hat. With an adjustable strap and a miniature box logo on the front panel, the Supreme camp cap is a slightly more subdued but still just as respected brand signifier. For decades before Supreme was a household name, its five-panel hats—perhaps more than limited T-shirts or decks—were a sign that you were in the know.

Today, the brand releases countless versions each year, including multiple colorways and materials per season. While there are dozens of options, our personal favorite is the wool version from the label’s on-going collaboration with Italian wool mill Loro Piana. One of the most illustrious wool mills in the world, Loro Piana traditionally produced fabric for some of the most revered fashion houses in Europe before launching its own in-house line. In an unexpected turn of events, the brand began collaborating with the New York streetwear brand on wool caps as well as highly sought after topcoats. Today, the wool camp five-panels are some of the most luxurious hats the streetwear label makes, and a personal favorite amongst collectors. A perfect year-round hat ideal for spring.

When talking Gucci, one of the first things that come to mind is its infamous bucket hat. Celebrities from Kate Moss to Jay-Z have worn the twill monogram bucket hat in magazines and fashion shoots galore, and through numerous music references and appearances the hat is a modern pop culture stalwart. That said, over the past few seasons, a new Gucci hat began to dominate headlines, its Yankees baseball cap.

Initially unveiled during the Fall/Winter 2018 runway show, the collaboration between the Italian fashion house and the MLB team is the brainchild of creative director Alessandro Michele, who himself is rarely seen without his trademark Yankees cap. Releasing in tandem with the label’s on-going partnership with Harlem-based designer and New York icon Dapper Dan, the capsule showed a renewed commitment and interest in New York culture at large. Featuring a repeating monogram and an embroidered vintage Yankees logo on the front, the hat adds a modern fashion edge to a classic '50s ball cap. As much a fashion accessory as memorabilia, the hat is equal parts Italy and New York in the best way possible.

When it comes to the outdoors, few labels can compare to Arc’teryx. The Canadian label produces everything from hiking and ski gear to military grade gear for the country’s army, specializing in technical fabric and weather resistant materials. While it’s pricepoint is normally steep, a few of its hiking pieces are more reasonably priced, its beloved Sinsolo hat included.

Made from a polyester plain weave fabric, the Sinsolo is water resistant, sun resistant and entirely packable. Despite being crushable, a specially designed weave allows the hat to stretch and the brim to keep its shape, meaning it will still be snug no matter how many times you wear it. Available in Arc’teryx’s usual vibrant array of colors, the Sinsolo is now especially popular following the rise of gorpcore and hikingcore thereafter, with street style regulars wearing them across the fashion circuit. Incredible quality for the price, the Sinsolo is ideal for the outdoors or a bad hair day.

When Hedi Slimane arrived at Yves Saint Laurent in 2012, he overhauled the entire house, famously changing its name to Saint Laurent Paris and retooling the entire aesthetic. With a renewed focus on menswear, the designer embraced rock and psychedelia in a way few other designers had, producing luxury skinny jeans, flannels, suede boots and, strangely enough, fedoras. Far from your lame uncle’s short brim straw party hat, these beaver fur wide brims in brown and black featured a satin bow and a subtle crown, almost reminiscent of cowboy hats.

Though difficult to pull off, for those who commit to the aesthetic, the Johnny Cash-esque “Man in Black” look is preternaturally cool. While the head-to-toe Saint Laurent look peaked a few years back, with a return to tailoring in sight, wide brim hats may very well be on the come back. If you’re interested in the Venice Beach psych-rock aesthetic, the Saint Laurent Paris fedora is a pivotal part of the look. With a serious price tag, these are not for the faint of heart—or wallet—and requires one to seriously commit. But, if you have the matching Wyatt boots and L17 leather jacket, it’s a must.

Italian-based Stone Island cleverly toes the line between tech and leisurewear, made with the elements in mind but—apart from specialty pieces and the notorious compass patch—for the most part, fairly tame. Its ongoing Supreme collaboration, however, is a bit less subtle. While the outerwear is the focus of each drop, on occasion the collaborative accessories have made waves, including the best in class boonie hat.

Released as part of the Spring/Summer 2019 capsule, the boonie hat was available in two colorways, a black and red desert camo. Floppy and entirely packable, that hat features two vent holes for breathability, a drawstring closure and loops running along the crown akin to a fishing hat. While resembling the sort of hat you would find at a military surplus store, given that this was a Stone Island collaboration, the material, construction and fit are all impeccable. Yes, this is the second Supreme hat we included, but when it’s this good, it’s hard to argue. While the collaboration—like any with Stone Island—sold out immediately, thankfully these still pop up on Grailed regularly. But, be wary, as they tend to move quickly.

Though the dad style trend may have peaked early last year, dad hats—and novelty caps in general—continue to pop up everywhere from the streets to the runways, and ironic fashion icon Demna Gvasalia is partly to blame. The designers quirky anti-fashion approach has always played a central role in his designs, from his time at Vetements to his current role as creative director at Balenciaga. With a fascination with the mundane, Gvasalia takes items rarely considered fashionable and recontextualizes them in a capital-F fashion context. The most obvious example is the Balenciaga dad hat.

Officially titled the “Logo Baseball Cap”, since his very first menswear collection Gvasalia has released hats that more closely resemble novelty merchandise than fashion accessories from a French luxury house. Yet, the juxtaposition is always incredibly well received, and in this case (alongside his gargantuan oversize tennis shoes) laid the foundation for the emergence of dad fashion as we know it.

Available every season, the hat shape and material stay the same, while colors and logos vary, from the Bernie Sanders campaign typeface to parent company Kering’s insignia. Simultaneously logo-heavy and nondescript, the Balenciaga dad hat is a modern fashion fanatic favorite. If you have one, you’re in on the joke. If you don’t, you simply don’t get it.

When Richard Stark founded Chrome Hearts in 1988, the brand was a small accessories line specializing in sterling silver jewelry and leather goods. Over the past 30 years, the Los Angeles label has evolved into a full-fledged lifestyle brand, with a ready-to-wear collection and special projects ranging from mahogany dining room tables to sterling silver inlaid chandeliers. While the jewelry is still its main selling point, the T-shirts, hoodies, and most importantly trucker hats have grown immensely popular following numerous co-signs from rappers and influencers galore.

While Chrome Hearts makes many trucker hats each season, by far the most popular is the F*ck hat, which features the expletive across the front panel in the label’s trademark old english typeface. Worn by celebrities ranging from Lil Uzi Vert to Bella Hadid, the hats notoriety on top of its exclusivity—Chrome Hearts is not available online and only sold at approved boutiques and its own retail stores—makes it a grail for many, selling well above its already steep retail price. Though the ostentatious aesthetic is certainly not for everyone, for those into the LA goth glam, the Chrome Hearts F*ck hat is fashion de rigueur.

For our avant-garde fanatics and serious fashion followers alike, a beret is an eternal symbol of chic. For others, it’s snooty, self-involved and unnecessarily elitist. Whatever your take, if you pay attention to Paris runways and street style photos, the beret is having a serious moment, with every designer from Dior Men’s to Louis Vuitton sending berets down the runway. While the trend may be peaking, if you plan on participating, you may as well honor the original.

A Noted francophile, Yohji Yamamoto has embraced the beret for decades, offering various iterations from overly slouchy to tightly fitted across his numerous sub-labels. While Y’s for Men makes plenty of respectable options, our personal favorites are the wool, droopy versions the designer includes in nearly every Yohji Yamamoto Pour Homme collection. The perfect addition to has delicately layered black silhouettes, Yamamoto is able to eliminate the air of superiority and pseudo-intellectual aura surrounding the beret and make it somehow incredibly endearing—even covetable. If you plan on giving the beret a go, trust the master to do what he does best. He won’t let you down.