Penchant for Preppy: Pull Off the Look of Success

Ralph Lauren. Brooks Brothers. Ovadia & Sons. No, not your bros in another state. Conservative clothing brands that are your fashion gateway to the good life. You hear that? If you wear a three-brass buttoned navy blazer with notched lapels you’ll soon be drinking diamond-flavored champagne and driving a McLaren F1. Yes, you will.

No, you won’t. But that’s just because preppy actually has nothing to do with affluence. It has to do with dreams, man. That’s right – big wet dreams about pulling up to the country club in madras shorts and hopping out to play cricket.

While you may think that’s not you, you have some variation of that dream. And if you want to show people what you’re worth, you have to get off the clearance rack once in a while and put on some respectable classic clothing. Start dressing with a little conservative flair and all the stupid shit you do suddenly get wiped away just like an NFL player’s suspension.

Just because the look might be high on tradition does not mean its low on sex appeal. Leave the putrid plaids, lobster-embroidered shorts and over-sized emblems for the dudes who actually do attend classes at Yale. You’re more interested in looking like a part of the rowing team. You do this by sporting juicy colors like grapefruit, lemon, Kelly green and lavender, in addition to bold hues like red and blue. Just no black. But you knew that.

Start with the basics. You don’t need a lot of choices; you just need the right choices. Get yourself a well-fitted, nicely made navy blazer. Then shop for tailored chino pants in classic khaki from J. Crew. When things are feeling right, add in a pair of red pants and you will have arrived at the pinnacle of prep. Like, damn you look dapper. Oh, and when you add in denim, make sure it’s a little shorter and slimmer than your other jeans.

Then saddle up to some colorful button-downs. Ralph holds the fashion reins in this area, so pony up the sixty bucks and purchase some pinpoint cotton oxfords. Top off the look with a bow tie, and you’ll get some serious clout with your boss and your buddies. Next you’ll need some solid and striped polos from Lacoste and about three finely knit v-neck sweaters. 

Now for the shoes. Kick your sneaks to the curb and add in a boat shoe from Sperry, driving moccasin from Tod’s or wing tips from Cole Haan.

Perhaps the most important aspect to pulling off preppy is that you infuse your own distinct style into the mix. Take tradition and tweak it. Try ditching the brown leather belt and wear an embroidered one from Smathers & Branson. Buy a watch that sets you apart or a cool pocket square that will give your blazer a boost. Or change the laces on your shoes. These are little things that will make you stand out from your preppy peers and ensure you don’t end up looking exactly like a page out of a J. Crew catalog. Just remember, when it comes to preppy, you’re dressing the dream, not taking over the personality of someone who might be living that dream.

Oh, and here’s what you’re not going to do: wear a sweatshirt from Dartmouth if you didn’t go there. And, unless you’re on a boat and seriously worried about a sunburned neck, you’re also not popping a collar. Got it?


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