My kinda clothes are just that, my kind. I draw heavy influences from both traditional Ivy and ’80s prep, but try to maintain a unique look. Adding my personal taste into an outfit means adding a dash of fun but always keeping it tasteful. I’m definitely a glass-half-full kinda guy, which can sometimes be tough in a genre of clothing outlined by ridgid rules. But I try to add my own flair into my outfits within those parameters, and if it means (respectfully) breaking some rules, so be it.
Some of the Ivy rules matter greatly to me while others don’t. My philosophy is that you have to know what you like and know what looks good on you. I’m a measly 5’5”, so vertical stripes are good for me, as are pants that cuff right at the ankle, so I incorporate these by necessity, so to speak. On the other hand, I like embroidered pants and polo shirts so these items make frequent appearances by choice.
The six items I wear most frequently are bengal-striped OCBDs, cashmere v-neck sweaters, corduroys, boat shoes, GTH pants/shorts, and polo shirts. These items allow for a lot of versatility as they’re all (minus the embroidered bottoms) practical. Additionally, they are canvases on which, paired with other items, let me add my own personality into the outfit. Above all, I think being comfortable and well dressed are not distinct notions.
The item I most wear in the winter months would be a sweater. I have many wool and even cotton sweaters, but my favorite is the cashmere v-neck. I often pair them with corduroys or chinos and either loafers or boat shoes. The shirt underneath varies between bengal stripe and turtleneck. A tweed sportcoat is a nice way to keep things a little more sophisticated while still being comfortable. When wearing one to class, usually I don’t wear a tie unless it’s the day of a tennis match. I typically pair it with corduroys or chinos, an OCBD, and loafers. When I do wear a jacket and tie, as a rule I try wear a full suit as little as possible and mismatch the jacket and pants. This is an example from the summer months when I can get away with seersucker. Staying true to my go-to-hell streak, I like to incorporate one bright or fun-patterned item into an outfit during the warm weather, contrasted by a solid item on the other end. My favorite way to do this is through pants.
Layers, I think, are the ultimate preppy device. One way I like to add a little more complexity to an otherwise one-dimensional outfit is by adding either a rugby over an OCBD or an OCBD over a polo, always worn with chinos and either boat shoes or sneakers. It creates a casual but put-together outfit, perfect for the weekend. — TREVOR JONES