
Is it just me, or are there saggy boots everywhere? Whether it’s flats or heels, mid-thighs or knee-highs, leather or denim, the options seem endless – and ubiquitous. The sheer versatility of the accessory makes it an endless accessory that can be worn for almost any occasion, complimenting almost any aesthetic, from indie rock to coastal grandmother. While ruffled silhouettes can be a turn-off for some, when paired properly, they quickly become a timeless staple, adding texture, volume and casual sophistication to any capsule closet.

For the layman, loose fitting boots date back to the 17th century – when the royalist supporters of King Charles I’s Knights wore tall moccasin boots that folded down to the ankle. These precise boots were later worn by naval officers and coxswains into the 20th century to protect against wind and cold weather. Notably, in 1981, the late Dame Vivienne Westwood debuted her now-popular pirate boots in her famous “Pirates” collection, which ran counter to punk’s underground anti-fashion movement and favored the New Romantics. Bringing punk into the glam rock era, the new collection echoes the theme of fetish wear: the sexy unisex look and glamorous style that still dominates the runways, mainstream fashion and social media today.

viviennewestwood.com
$835.00
It was only a few years later, in the late 90s, that this casual style gained traction in the streetwear scene when supermodel Kate Moss was photographed wearing her own pair of Westwood pirate boots. A product of punk attitude and sartorial anarchy, they quickly became one of the most desirable and revolutionary fashion trends of the decade and continued into the early 2000s – both in real life and on the silver screen. Prada-wearing femme fatale Anne Hathaway recently revealed that her favorite on-screen outfit was a revamped Andy Sachs, which included a pair of knee-high suede lounge boots. Not to mention Vivian Ward’s iconic thigh-high patent leather boots from Pretty Woman, a staple of Halloween costumes and etched into our eternal collective fashion memory. (In 2020, the boots sold for £31,250 at an auction in London.)

Since then several vintage revivals have occurred. In the past, baggy boots were usually designed in neutral, earthy colors with little embellishment. According to Fashion Snoop’ accessories director Anoush Mirbegian, we are now seeing a decidedly more eccentric adaptation, influenced by the rise of avant-garde, motocross and “sentimental” fashion – a trend driven by shoppers’ desire to connect with their purchases. This trend also returns to Westwood’s subversive roots of her own creation.
Balenciaga memorably embraced accessories in its early fall 2016 collection, designed by creative director Demna, showcasing knee-high reflective silver stiletto heels. vetements’ spring 2017 collection followed with colorful, high-waisted satin casual boots that blurred the line between boots and pants (hello, pant boots). for fall 2019, the collection was a mix of the best and the brightest. luxury brands like Saint Laurent, Gucci and Isabel Marant experimented with unconventional toe shapes and ruffled silhouettes. For the Y/Project Spring/Summer 2023 collection, creative director Glenn Martens took oversized styles to a whole new level by twisting structures to create mise-en-scène pieces that amplify the Belgian’s innovative approach to fashion. In the past year, we’ve seen the likes of Kim Kardashian, Hailey Bieber, Rihanna and Ari Lennox don their own big pairs of shoes. Hathaway clearly stands out in a way that is unique to her newfound personal style.

It’s been proven time and time again that casual boots dominate the turbulent trend cycle. Of course, we’re all a little tired of the relentless and exaggerated micro-trends that dominate our social feeds, especially our TikToks. So we usher in the season of the baggy boot – the epitome of comfort, practicality and raw rebellion. Wear yours with maxi dresses, mini skirts, fitted pants, or just leggings and embrace the distinctive pants-free look (and why not?). . Over-accessorize your heart or let the shoes say it all. Do what you want to do. Slouch!