![]() This is why a younger man in prep clothing dresses essentially the same as the seasoned man in his 50s or later. In fact, the prep fashion is about authentically preserved clothing and looks. The prep style is not about buying into the latest trends or paying for flashing new clothes every year or less. A large part of that spirit is European legacy, longevity, tradition, and heritage. By that measure, good old-fashioned penny loafers can be infinitely cooler than any four-figure sneaker.To first get the style, you have to understand the spirit behind the look. “These edgier streetwear brands are less democratic than a brand like ours,” Bastian says, “which has great price points and high quality and is enduring.” Ultimately, maybe that’s why prep has remained: It’s a sort of anti-hype, the elements so attainable and unassuming that it’s up to the wearer to add the swagger. Their simplicity and lack of fuss leave ample room for every man to make them his own. In one man’s hands, they’re Main Line blue blood in another’s, Silver Lake fashion bro-or maybe both at once. “It’s all how you put it together yourself.” “The basic elements, like chinos and oxford-cloth shirts, cashmere V-necks, down vests… they’re all very simple,” he says. His first collection, in stores now, began with perfecting the staples that the brand made famous. “Twist it any way you want to twist it, that’s the beauty of it,” says Michael Bastian, the designer who is guiding Brooks Brothers-the preppy mothership-back from the brink. The new school is a diverse class, cross-pollinating Ivy with everything from streetwear to Neapolitan sprezzatura. What differentiates the current wave is an appreciation of technical minutiae coupled with a more expansive view of the style’s potential. “We’re going through an unstable phase,” Jules says, so “it makes sense for people to look back toward this touchstone that’s reassuring.” So why, at a time of great social reckoning, is preppy style striking a pinwale cord? Actually, it fits a pattern: The golden age of Ivy style overlapped with the Civil Rights Movement the ’80s Preppy Handbook resurgence followed the counterculture turbulence of the 1970s. Trunk cotton needlecord jacket, $929, and trousers, $310 Jake’s oxford-cloth button-down shirt, $205, and silk repp tie, $135 Sid Mashburn calfskin tassel loafers, $495 Bottega Veneta sunglasses, $455. “The white picket fence, a good education and all the rest of it, the things that Black generations weren’t permitted to have… Ivy democratized the idea of having access to luxury, that we could all have a piece of that rock.” ![]() “It signifies social access,” Jules says. and James Baldwin, who gave it political resonance. According to Jason Jules, coauthor of Black Ivy: A Revolt in Style, out in December from Reel Art Press, the style has been re-appropriated for almost as long as it has existed, including by Black Americans of the ’50s such as Martin Luther King Jr. That attitude was perpetuated in various forms, as different subcultures from skaters to musicians adopted elements of Ivy-think of Kanye West’s prep-hop look from his early-2000s The College Dropout days or LeBron James walking the tunnel in a Thom Browne sack suit, oxford-cloth shirt (and shorts) included. “The irony of preppy style is that it was born out of a spirit of rebelliousness.” While prep today is associated with a certain type of country-club politesse, the aesthetic “began with college kids around and having fun,” says Jack Carlson, founder of Rowing Blazers, a brand that’s bringing irreverence back to Nantucket Reds and needlepoint belts. What those principles are, however, is endlessly up for debate. It’s a uniform, he explains, which communicates that a man “still adheres to certain principles.” ![]() “You go to work in an oxford button-down shirt, a blue blazer, khaki slacks and that, today, is dressing up,” Press says. Equal parts laid-back and decorous, it’s also particularly well-suited to the current moment. Press, an elder statesman of Ivy outfitters. “It’s the quintessential American look,” says Richard Press of J. Ralph Lauren has been riffing on it since he first set up shop, and a slew of young brands, including Brooklyn’s Wythe and London’s Jake’s, have sprung up with gimmick-free re-creations of the original Ivy staples. Prep is the rare fashion trend that has endured largely unchanged since it was popularized. Ivy style came to the fore almost a century ago, and you can probably already picture the look: soft-shouldered sack suits, hardy oxford-cloth button-downs, rugby shirts and repp ties. Of course, little about this is really new. How Dickies Went From Blue-Collar Bastion to High-Style Staple TAG Heuer Just Dropped a Limited-Edition Carrera Chronograph With a Striking Crimson Dial Prices on the Luxury Watch Market Are in Flux, But Dealers Say Business Is Better Than Ever
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