By Olivia Muenter
Updated: Apr 01, 2019 @ 11:50 am
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Developing a sense of style is no easy feat. First you have to identify what it is you actually like, and then you have to go out and find pieces that fit your wardrobe, budget, and aesthetic. The idea of building a wardrobe full of preppy clothes can be overwhelming, even if you know that that’s your preferred sense of style. Say you’ve fallen in love with the outfits of people like Carly Heitlinger and Kiel and Sarah Patrick on Instagram. Maybe you can’t get enough of watching re-runs of Gossip Girl just for Blair’s wardrobe. You clearly love the idea of a preppy wardrobe, but all the Instagram inspiration in the world isn’t quite getting your closet where you want it to be. Your best bet? Start with staples.

Breaking a style down into a few must-have pieces to build a wardrobe around is key to creating a sense of style, especially one that centers around a very specific aesthetic. Whether you’re leaning toward the more feminine side of preppy style or have a thing for mixing classic staples with high fashion trends (looking at you, Gossip Girl fans), there are a handful of pieces that every preppy wardrobe should have front and center — and plenty of preppy brands to shop.

A Classic Button-Down

LOFT Chambray Button Down Shirt


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No preppy wardrobe is complete without a crisp button-down. It’s understandable if you mostly associate button-down shirts with middle-aged men, but it’s helpful to think less your dad and more Diane Keaton in Annie Hall. The beauty of a button-down is that it works with just about everything. Want to go casual? Find an oversized option and pair it with jeans. Interested in something a little bolder? Wear it buttoned under a vest or bright sweater. Not sure what to do with it at all? Not a problem, because a classic button-down looks good all on its own.

Shop Similar: Eloquii Premier Button-Down Top, Misha Nono Husband Shirt

Timeless Sunglasses

Tom Ford Eugenio Sunglasses


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Like any style of dressing, accessories are an important part of developing a preppy sense of style. And while plaid scarves and monogrammed canvas tote bags (you know the ones) certainly play an important role in any true prepster’s closet, there is arguably no item more essential than a pair of timelessly stylish sunglasses. Even if you’re not wearing them on board your family's sailboat anytime soon, classic Wayfarer frames make it look like you might be.
 

Shop Similar: Ray Ban Original Wayfarer Classic, Quay Australia Walk On Sunglasses

Boat Shoes

Sperry Women's Authentic Original Boat Shoe

 

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Speaking of boats: regardless of whether or not you’re going on them anytime soon, boat shoes are a preppy must-have. Even though Sperry’s Sahara-colored boat shoes are as classic as it comes in terms of preppy footwear, there are hundreds of other options if you want to switch it up for something a little brighter, too. Sperry offers basically every combination of pattern, color, and fabric available for their boat shoes.You could even match them to your button-down, if you want to go really wild.

Shop Similar: Sperry Women’s Sailor Boat Shoe, Sperry Women’s Seaport Boat Shoe

Layering Pieces

Gap Longline Open-Front Cardigan

 

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A big part of a preppy wardrobe is knowing how to layer. The best part of this is that layering can look like whatever you want it to. A quilted vest, zip-up fleece, or button-down cardigan are all preppy staples and can styled in dozens of different ways. Looking for something a little less casual? Invest in a blazer. Blazers are a preppy staple, but are also a staple of basically every style of clothing. Pair a navy blazer with a T-shirt for a more modern look, or a tailored button-down if you’re looking for something more traditional.

Shop Similar: Land’s End Women’s Quilted Vest, Eloquii Double-Breasted Blazer

Something Plaid

Tasha Knotted Gingham Print Headband


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A closet full of preppy clothing is nothing without at least a little plaid. Plaid is a pattern that can be intimidating for some people, especially outside of fall and winter, but there are so many different interpretations of this trend that it shouldn’t be something you’re afraid of. If you’re new to plaid, layer on a light plaid scarf on top of a plain sweater or T-shirt. If you’re into trends but unsure of plaid, try out a statement headband with a light tartan. And if you just can’t get enough of the pattern, invest in some bold cropped, plaid pants (navy and green is a great plaid combination, if you’re wondering where to start). And, of course, there’s always plaid boat shoes, too.

Shop Similar: J.Crew Martie Black Watch Stretch Wool Pants, ASOS Oversized Plaid Scarf