The Latest Look From the Preppy Handbook Is a Real Winner

This fall, letterman sweaters are the reigning champs of style.

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Band of Outsiders
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When I graduated from high school, I couldn't get rid of my pleated uniform skirt and shiny penny loafers fast enough. Sure, I may have loved them as a teenager—so much so that I would have worn them every day even if they hadn't been a dress code requirement—but now that I was heading to college in New York, those beloved wardrobe pieces didn't quite fit into my vision for my new, cooler self and I gladly traded them in for a more "grown-up" kind of uniform. But these old-school items have recently re-entered my life (and my closet). The fashion world is a pendulum, and certain preppy essentials, especially, have re-emerged as major trends over the past few seasons. Everything from pleated skirts to loafers have experienced a resurgence lately, but my latest favorite, the letterman sweater, is truly in a league of its own.

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Rendered in both V-neck pullover and cardigan styles, this iconic knit is distinguished by one or two large letters stitched just under the left shoulder. Originally, the initials represented the school of the athlete wearing it. Sometimes they'd feature stripes on the sleeve, which indicated the number of years the wearer had played on the team. The style dates all the way to 1865, when each star player on the Harvard University baseball team was awarded a giant "H" to pin to the front of his gray uniform shirt. The trend was slow to catch on, but once the Harvard football team followed suit a decade later, the sweater picked up steam.

Alexander Wang
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Sports teams across the country adopted the varsity sweater as a sign of athletic prestige (it also served as the universal sign of "going steady" when a male athlete gave it to his girlfriend to wear). Good news: these days, you don't have to be an MVP, an athlete's steady, or a benchwarmer to slip one on. The classic V-neck or pullover styles are still used as official athletic merch in high schools and colleges all over the country, but fashion designers have also added modern updates with unexpected fabric choices, colorways, and prints.

Alexander Wang showed a sweater-jacket hybrid for the label's sportswear-inspired spring 2010 collection that featured a double-breasted front, patent leather details, and a glittery "A." In true Wang fashion, the designer proved that with a few embellishments, even the most collegiate items can be edgy. Jil Sander kept things simple with a striped pullover during the pre-fall 2012 show; Beyoncé famously wore it on her much-photographed south-of-France vacation a few months later. Then, Rag & Bone debuted a deep V-neck version for spring 2014 that quickly became an editor's favorite. Finally, there's Maison Martin Margiela, whose recent fall 2015 heather-gray sweater nods back to the style's Harvard roots with large black lettering across the chest.

Maison Margiela

Despite its runway clout, the style has seen its fair share of hurdles over the years. Many people ignore it in favor of the wool varsity jacket (which actually came afterward, around 1930, but has since surpassed it in popularity on mall racks and bookstores alike). The varsity sweater deserves better. The classic knit is more versatile than its flashy, leather-sleeved counterpart. This is a sweater that can swing from Ivy League prepster to sports star and back in a second—and the versatility doesn't end there. Who can forget Grease's resident bad boy, Danny Zuko? Paired with a black tee and slicked-back hair, he managed to make his white and red Rydell High cardigan look rock-and-roll.

My first varsity sweater wasn't mine, technically. It was passed down from my dad when I was a teenager, an oversize navy cardigan with a giant "C" just below my right shoulder. It was so comfortable I could wrap myself up in it, and that's why I wore it with almost everything. Even though you can find a new version at pretty much any retailer now, I still prefer my varsity sweaters secondhand. Luckily, there are more than enough places that sell them. I found my second one, a pullover with an "R" stitched across the chest, buried under a pile of clothes in a Brooklyn thrift shop.

Just like donning collegiate-inspired pieces like plaid skirts and prepster slip-ons, wearing varsity sweaters today makes me feel nostalgic for those quintessential school experiences. It reminds me of football games and hanging out on the quad—even though the earliest memories from the sweater aren't even my own. Whether you get yours from a thrift shop, your grandfather's closet, or a school bookstore, knowing that the style comes embedded with this kind of history is exactly what makes it so special.

Edwin

Band of Outsiders, $198, lagarconne.comAlexander Wang, $275, farfetch.comMaison Margiela, $955, net-a-porter.comEdwin, $139, edwin-europe.com.

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