Big Boots Are Back, Big Time
From ’90s hip-hop staple to Y2K uniform component to 2024 outfit essential, the resurgence of oversized footwear confirms that time is a flat circle.
“My first reaction when I saw them online was ‘Oh my god, let’s f—--- go!” says A$AP Nast, capturing the excitement many felt when seeing Louis Vuitton’s internet-breaking Timberland boots for the first time. "I went to the LV studio in Paris and got to see them in person,” Nast continues. “I was just so excited that the collaboration was actually real.”
Big boots, like many high-fashion reference points, are rooted in utility. From the marshes and swamps of the Southeast to the dusty plains of the Midwest, this type of footwear aims to keep entrants out while maintaining stability. In the past year or so, this everyman practicality has been applied to the runway, with the trickle-down effect resulting in a renewed appreciation for boots typically associated with the cold-weather months. For people like Nast, they never truly went away.
“I can't imagine my life without a pair of what we call ‘constructs,’” he says. “They're a staple because you can wear and style them with just about anything. They pull together even the most lackluster outfits—it's almost like magic. New York City and the entire hip-hop community have glorified them for so long. They're not going anywhere.”
The Pharrell Phenomenon
For Fall/Winter 2024, Pharrell Williams riffed on the idea of Americana, bringing Western-themed looks to his second show as creative director of Louis Vuitton menswear. Among the flared denim, cowboy hats and “Cowmooflage” Canvas trunks, Timberlands rounded out key looks. It’s a melding of opposing styles: Timberland’s resilience and durable nubuck leather combined with the shimmering glamor of Louis Vuitton.
The incorporation of Timbs into the show—LV’s monogram is pressed into the classic 6 Inch Boot’s upper and inner tongue—may have elicited some skepticism: What has become a symbol of hardened, working-class life, is being repurposed for those removed from that world. But Pharrell came of age during an era where Timberland was ascending as a cultural touchpoint and has even paid homage to the big boot already.
In the mid-2010s, the multi-faceted creative released a slew of Timberland collaborations through Bee Line, a colorful subdivision of Billionaire Boys Club. Instead of electric blues and hot pinks, Pharrell took a more muted approach, creating what looked like Timbs soaked in dye, while enlisting peers in his network for more statement interpretations. This eclecticism would define Bee Line’s relationship with Timberland going forward. 10 years later, this moment in streetwear history makes the Louis Vuitton collaboration feel like a full-circle moment.
“Dressed in White, I Like Black Timbs and Black Hoodies”
As rap penetrated the ’90s mainstream, Timberland enjoyed a wider cultural cache, made possible in part by its unofficial East Coast ambassadors: Jay Z, the Notorious B.I.G., Mobb Deep, Wu-Tang Clan and Nas.
“Suicidal Thoughts,” a track off Biggie’s magnum opus, Ready to Die, abandons the idea of nature vs. nurture, trailing off into eery nihilism. Before taking listeners on this journey, B.I.G. opens up his verse with a couplet that juxtaposes grim fantasy with material reality (“It don't make sense, goin' to heaven with the goodie-goodies, dressed in white, I like black Timbs and black hoodies”). White clothing gets dirty too easily, but black Timberland boots are built to survive.
Hip-hop’s lasting impact on the big boot is traceable not only to Pharrell, but designers like Virgil Abloh. During his prolific run throughout the 2010s, Abloh successfully eroded the barrier between streetwear and luxury. He also lent his touch to Timberland, putting out an all-velvet version of the 6 Inch Boot through Off-White, toying with the idea that creasing one’s Timbs is sacrilegious. Aesthetically, it was a stark contrast to the deconstruction that defined his work with Nike. Perhaps Abloh recognized that Timberlands were luxurious in their utility and didn’t need to be surgically taken apart for this to be understood.
The Rise and Rise of UGGs
UGG boots, a fuzzy, altogether cozier member of the big boot family, are more at home on Los Angeles sidewalks and McMansion carpets than steely, factory floors. For all their differences, the two brands find a common thread in creating oversized footwear that lasts. A cursory look at some of UGG’s creative partnerships in 2023 hints at the sheepskin-lined boot’s omnipresence: Palace, Telfar, Madhappy and The Elder Statesman.
While the Telfar x UGG collection hones in on the New York label’s signature motif, the Palace collaboration takes the brand into stranger territory, emerging as an irreverent wink. Embroidered motifs of tiny devils, surrealist suns and a flipped Snickers logo adorn Palace’s UGG Tasman Slipper. Both interpretations—one maximalist, the other minimalist—highlight the versatility of UGGs and why brands enjoy working with them as a canvas for expression.
Another collaboration, this time with Collina Strada, looms on the horizon, blending saccharine pastels and literal spikes through the vehicle of a mary jane. It’s an aggressive reimagining that one could imagine a cold-blooded schoolgirl from Battle Royale throwing on. Far removed from in-line releases, this open-minded way of operating has allowed UGG to maintain its ubiquity in an era defined by collaborations.
Y2K Comes Back Around
As the 2000s rolled around, the defining aesthetic frameworks included technological optimism and oversized garments. The latter manifested across both popular culture with NFL jerseys in triple XL sizing and subcultures, as ravers, skaters and pop-punkers rocked JNCOs, Girbauds and ICEBERG denim. Baggy fashion was on its last metaphorical legs as the Hedi Slimane-driven era of skinny jeans was primed to take over.
UGGs, meanwhile, found themselves saddled to Juicy Couture tracksuits. Celebrity It girls of the era like Paris Hilton, Kim Kardashian and Vanessa Hudgens were notable proponents of the look, creating some of the decade’s most iconic street style snapshots. The Y2K version of the girl-next-door look may begin with velour on top, but it ends with UGG boots on the bottom. Detractors at the time were quick to paint this kind of outfit as trashy, something best suited for morning voyages to the cafe.
Perhaps ironically, this artful dishevelment would continue to persist years later, best exemplified by the likes of Jonah Hill and the “scumbro” movement. On the runway, these styles come to mind through Glenn Martens' Y2K-indebted, extra baggy pants at Diesel, while Miuccia Prada has revisited micro mini skirts and other low-waisted denim creations at Miu Miu.
Although its members weren't fully present to experience the early 2000s, Gen Z is immersed in Y2K nostalgia and fixation. PinkPantheress’s “Just for Me” video could fit seamlessly into a TRL countdown, arriving with all the fixings of the era: moody text written in handwriting that may or may not be tear-stained, a sound system juxtaposed against an all-white physical encasement, flip phones and fish-eye cutaways.
The Expressive Allure of Big Boots
Today’s wardrobe consists of everything from baggier bottoms to mesh tops to butterfly clips. UGGs and large boots in general—see how Danner boots are currently footwear de jour for cool kids everywhere—are able to blend into this canon of contemporary outfits.
The big boot resurgence is indicative of how personal style and expression are becoming far more customizable. Our conception of footwear has been steeped in a binary for years: sneakers and non-sneakers. It speaks to a new generation’s broader worldview where rigid classifications are out and fluidity is in. Timberlands and UGGs have asserted themselves as the ideal canvas: Malleable silhouettes that can be stretched in infinite directions while retaining a DNA immune to changes in taste.
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