40 Cute Preppy Outfits That Put Gossip Girl To Shame

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Have you always wanted to look like a private schoolgirl with their cute outfits? If so, here are the cutest preppy outfits that you can recreate!

When we talk about preppy outfits, we think of Blair Waldorf and Serena van der Woodsen – the iconic queens of preppy outfits. In the world of Gossip Girl, it’s all expensive clothing – after all, private schools are exclusive, preppy, and chic. You can’t help but be a little envious at their outfits too: a little plaid skirt goes a long, long way.

Preppy outfits usually include plaid in any form – skirts, trousers, blazers, even hats. This aesthetic also includes sweater vests, sweaters, pleated skirts, pencil skirts, turtlenecks, button-down shirts, long-sleeve blouses, blazers, and sometimes hoodies.

It’s also important to note that preppy outfit colors are mostly understated, so if you want to go for a preppy look, it’s best to go with classy colors like beige, cream, brown, and black.

Of course, you can add pops of color but make sure they are on the pastel-ish side. It’s also safe to play around with patterns like plaid, argyle, and animal prints, just don’t go overboard1

The outfits featured below are completely shoppable, so if one (or two… or three!) has caught your eye, just click on the photo and it will take you right to the website to order.

Let’s go and build your preppy outfit!


The Cutest Preppy Outfits




Preppy houndstooth outfit with knee high black boots


Get this set on Storets




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Beige sweater vest with plaid skirt


Get this on Princess Polly




Cute preppy outfit with purple sweater vest and tennis skirt


Get this skirt on Storets




Cute pink preppy outfit with tweed skirt and jacket set


Get this set on Love Shack Fancy




Tweed skirt and blouse


Get this on YesStyle




Cute and preppy grey sweater vest outfit with thigh high boots


Get this sweater on Storets




Cream knitted sweater with white shirt and skirt


Get this on YesStyle




Michigan tee and white pleated skirt


Get this on Princess Polly




Light blue houndstooth preppy outfit with jacket


Get this jacket on Storets




Cute beige knit vest outfit


Get this knit vest at Storets




Cute preppy houndstooth dress


Get this dress at Anthropologie




Grey hoodie with plaid pleated skirt


Get this on Princess Polly




Argyle print sweater and black pleated skirt


Get this on YesStyle




Long pink tweed jacket


Get this coat at LoveShackFancy




Cute pink preppy tweed skirt and jacket set


Get this set at Pink Lily




Cute preppy houndstooth pinafore dress


Get this dress at In The Style




Long pink plaid coat


Get this coat at Lulus




Cute argyle sweater look


Get this sweater at Storets




White tank crop with green plaid pleated skirt and jacket


Get this on Princess Polly




Cute red and green preppy plaid dress


Get this plaid dress at Red Dress




Black and white tee with pleated skirt


Get this on YesStyle




White crop top with pleated plaid skirt and sneakers


Get this on Princess Polly




White long sleeve button shirt with printed sweater vest


Get this on Princess Polly




Cute Thanksgiving outfit with plaid tweet skirt and knee high boots


Get this skirt & outfit at Pink Lily




Beige blazer and pleated skirt and blouse outfit set


Get this outfit set on YesStyle




White ribbed sweater


Get this on Princess Polly




Cute preppy Christmas outfit with red plaid skirt


Get this skirt at Red Dress




Cute preppy outfit with brown plaid cardigan


Get this sweater at Pink Lily




Cute pink preppy tweed dress


Get this dress at Shein




White long sleeve collared top with black pleated skirt


Get this on Princess Polly




Cute grey pinafore dress


Get this on Pink Lily




Cute preppy taupe tweed dress


Get this dress on Red Dress




Cute beige tweed coat


Get this coat on LoveShackFancy




Ribbed bodycon dress with dark brown blazer


Get this on Princess Polly




Yellow blazer with white turtleneck and white pants


Get this on Princess Polly




Blue and white sweater vest with white pleated skirt


Get this on Princess Polly




Cute pink tweed dress


Get this on Red Dress




Brown argyle sweater with white pleated skirt


Get this on YesStyle




Cute preppy outfit with pleated skirt


Get this set on Storets




White blouse with bow and black skirt


Get this on YesStyle


Have you found your next outfit from this list? Let us know in the comments section! If you’re still looking for more fashion inspo, check the posts down below.


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