When you’re unsure of how to dress, you can default to preppy style. There’s no blunder in appearing put together and clean, and this timeless look, originating from the early 1900s, has outlasted any and all trends.
But there’s a line between a respectable, thoughtful gentleman and some guy named “Winston” who complains incessantly that Papá’s boat is too big to berth at the Marina. Here are some comprehensive tips on how to dress preppy without inviting eye-roll emojis:
Table of Contents
Preppy Style Essentials
Sweaters are that cozy garment you spend hours snuggling up in at the library (or so it appears). This collegiate staple is comfortable, versatile, and it works on-the-go. Crewnecks and V-necks can be layered over button-downs to show off the quintessential preppy collar.
What sets preppy sweaters apart from athletic ones is the difference in fabric. Ivy-inspired preppy sweaters are woven with cotton, wool, and cashmere, while other sweaters may be made with a polyester and nylon blend. You can have some fun with patterns like argyle and cable-knit, but try to limit mixing and matching. Prep school style, rooted in early 20th century New England fashion, is intended to be pretty tame.
You may have seen badminton enthusiasts and Wolf of Wallstreet characters tying sweaters around their necks and waists. We suggest you pass on this one. It looks pompous, like a Pomeranian wearing a bowtie.
Whether on a Polo, an Oxford button-down, or a seersucker shirt, the collar is a preppy hallmark.
Polos, created by the Brooks Brothers’ early president, are adapted versions of 19th-century athletic shirts worn by polo players. These shirts had buttoned-down collars to prevent them from flapping in the wind. And thus the smart, casual, sporty polo shirt was born.
Wear polos in pastel colors, even in striped prints, but do not pop the collar. You won’t look like a colonial general or a fancy Britishman (though why would you want to?). You will, however, look like a figurative tool.
The gist of preppy style is that it’s somewhat formal, somewhat elevated, but definitely not Monopoly-man chic. This Ivy-inspired aesthetic hits a healthy balance between student and professional for a smart everyday look. Chinos are the perfect pants to fit this mold.
Chinos are straight-fit pants made from lightweight cotton with a tighter fabric weave than khakis. Due to its polished fabric finish, and its slimmer fit, these pants reside in the class of formal casual wear.
Chinos are typically beige, navy, or blue, but feel free to go pastel and even try bold colors. We’re going to discourage full-on Go To Hell Pants, though. For a presentable daily look, you don’t want “guffawing on astroturf while wearing a peacock feather hat” vibes.
As Tommy Hilfiger the man himself once said, a navy blue blazer “can take you from office meetings to dinner out with friends.” This prep style staple can be dressed up, dressed down, and accessorized. The right fit blazer should hang straight down, without being too restrictive or oversized.
Here’s a mashup we’re excited about: the sweater blazer. Comfy, huggable material with lapels so that you can look mind-twistingly casual formal, but casual? Yeh.
Clearly our favorite component of prep style. Long live ties, bowties, pocket squares, and lapel pins. Accessories add a flair of color, and just general “tricked outness,” to this overall conservative look.
Skinny ties and bowties can be worn with a blazer, a V-neck sweater, or with just an oxford button-down. Go for fun prints. A modest dose of bold design will allude to your keen eye and good taste; emphasis on “modest.” Try pairing an If the Shoe Fits Bow Tie with a pastel shirt.
Since we’re talking preppy style and not full-blown formalwear, you don’t need the whole gamut of accessories at once. If you’re wearing a pocket square, consider going tieless.
You can’t nail prep style without the perfect pair of semi-formal, but also nautical and sporty, shoes. Sperrys were invented when Paul Sperry, an avid boater, needed shoes that would prevent slipping on his watercraft. He cut patterns into his shoe bottoms for more grip, and voila: we have stylish boat shoes, a preppy man’s everywhere footwear.
Protip: never ever ever let your socks show when wearing boat shoes. You should definitely opt for no-show socks:
Another closed-toe lace-up shoe that looks smart as heck is the Oxford shoe. These shoes are characterized by closed lacing and can be dressed up or down. Remember the modest bold rule? Try pairing Oxfords with some neon laces.
Are you a nerd, goth, prep or jock?
The truth is, all of the above. This isn’t high school, though Riverdale might be repopularizing the retro preppy style. We’ve created this guide to help you navigate elements of preppy style so that you can shape your own personal look, in a way that’s natural to you. By all means, do you: wear chinos with high tops; wear blazers with tee shirts. Though if you’re ever at a loss for what to wear, just know that preppy style will always be “in style.”
What’s a pretentious preppy look you can’t stand? Let us know in the comments below.
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