It used to be that men’s style evolved at a glacial pace. But in recent years, as guys have started taking a greater interest in what they wear and and the design process and inspiration behind those garments, trends have turned over at a far greater rate. Right now, the goth ninja look is having a moment. Before that, it was the urban lumberjack and before that it was the traditional prep.
Here’s the thing about that last one, it never really went away. Classic prep style—aficionados also refer to it as “trad” or “ivy” style—will always have a place because the items are the foundations on which American menswear is built. From time to time, the world of high fashion may anoint preppy style “in,” but true trads could care less, because they’re confident in the knowledge that what looked good on their father and grandfather before them will always hold up, regardless of whether or not it coincides with a reprinting of prep style bible Take Ivy.
To help you pull off the prep look, we curated a selection of garments that will have everyone wondering where you went to boarding school.
1. MICHAEL BASTIAN COLLAR SWEATSHIRT
A graduate of prep bastion Babson College, designer Michael Bastian is an expert at taking traditional Americana style and adding his own tweaks to make it feel current today. With its winged logo and suede elbow patches, this sweatshirt fits in just as well at the University Club as it does at a downtown club.
2. QUODDY TRUE PENNY LOAFER
All of Quoddy’s shoes are handmade in Maine on wooden benches with just leather, needles, and thread…and centuries of passed-down craftsmanship. These penny loafers are constructed of beautiful Horween leather and a glove leather lining. And yes, you should definitely put the penny inside.
3. DANIEL WELLINGTON CLASSIC GLASGOW
Preppy style isn’t about being ostentatious, it’s about being understated and refined. With a classic blue-and-white ribbon band (Yale colors) and a minimal dial design, this ultra-thin watch embodies that spirit to a T.
4. HARROW SQUASH RACQUET
Squash is one of those sports that you probably only know about if you went to prep school, or are friends with someone who did. But if you ever get a chance to play, do it. It’s a ridiculously fun game that is considerably more physical than tennis because it’s played in tight confines that make running into your opponent and the wall a regular occurrence. And like other preppy sports such as golf and tennis, it’s a great way to network.
5. TUCKER BLAIR NEEDLEPOINT BELT
We can’t all have a girlfriend named Muffy to stitch us a needlepoint belt. That’s why there’s Tucker Blair. The brand specializes in the casual belts and puts a fun spin on them with patterns like this with Jeep Grand Wagoneers, the ultimate wood-paneled preppy SUV.
6. MOSCOT ACE
From $290, moscot.com
A New York City stalwart for 100 years, Moscot eyewear teamed up with the Ace Hotel, which is becoming an institution of its own with outposts in every cool city in the U.S. The collaborative sunglasses have a two-part frame, where the upper is a black acetate and the bottom is gunmetal titanium. It’s easy to picture a Kennedy wearing shades like these.
7. J. PRESS TRIM FIT OXFORD
Started near the campus of Yale University in New Haven more than 100 years ago, J. Press is an Ivy League institution so you can feel confident in their ability to produce the preppy staple that is the oxford button down shirt. They’ve slimmed down the fit, but still make them in the U.S. with the signature flap pocket on the chest.
8. RRL SLIM FIT CHINO
Whether you call them chinos or khakis, they are a must-have in any trad wardrobe. RRL has nailed the look with a pair whose design is modeled after the pants worn in the 1960s. They have a straight leg that tapers a little bit so that they fall perfectly on those penny loafers.