Preppy Winter Outfits

Zara Plaid Crop Top

Here on LivingLesh, I am constantly talking about how to live your luxurious lifestyle while still staying on budget. That luxurious lifestyle is inclusive of travel, home, and, of course, creating your own personal luxury style. We constantly debunk the myth that in order to live a luxurious lifestyle, you have to have a six-figure yearly salary to cover that lifestyle. One such style that is often thought of as luxurious is the preppy look. But I’m here to tell you that you can create preppy winter outfits without breaking the bank.

Just like the idea that luxury comes with a price tag, apparently, according to people I have spoken to, so does the idea of what preppy means. But at its core, the preppy look is just an aesthetic – not a social class. You don’t have to have a high-end budget or send your kids to private school to embrace the preppy look. You can just enjoy the aesthetic! That’s why I want to show you some of my favorite preppy winter outfits, so you can see for yourself how easy it is to enjoy the preppy look, no matter what your budget may be.

Preppy Winter Style

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actual top from Zara – cropped plaid top


As the weather begins to grow colder, I sometimes find myself running out of outfit ideas. After all, when you’re in the depths of a Philadelphia winter, no matter how much of a fashionista you are, you often find yourself more worried about how on earth you’re going to stay warm than you are about how you’ll look doing it.

That being said, I have recently become a big fan of the preppy look, and it has been changing the game for me. There are so many cute ways to style it, and it’s a look that works so well in the winter months due to the pieces and patterns naturally associated with it.



The definition of preppy and the style surrounding it has its roots in the style that students wear when they attend prep school. So while the style did originally originate with people with money, it has changed so much over the years. Now whether you actually attended a prep school, your children attend, or you just saw the style from watching various movies, you can make the preppy look part of your wardrobe.

Most of the style you see when looking at examples of the preppy look involves plaid or argyle, and in many cases, the style is not just worn by those who attend prep school. If you think about it even through the lens of pop culture, Cher from Clueless had a preppy style, but she attended a public school. Now, she was rich, but her style could be adapted to a more standard budget and not cost half as much money as she made it seem that she was spending in the film.

If you do some research on the preppy style, you can see that the bulk of the style deals with a lot of plaids, skater skirts, argyle, and layering – which makes it the perfect aesthetic to embrace for the winter season. A lot of the layering – which you all know is my favorite thing to recommend to extend your closet – deals with long-sleeved button-up tops and sweater vests. If you’re a fan of Gilmore Girls, think about Rory’s style. Much of what she wears, especially during her years at Chilton, is a part of the preppy look, and due to the show taking place in Connecticut, her outfits are always conducive to the colder weather.

Another reason that the prep look is great for the winter season is that many prep schools made their uniforms – which the prep style is based around – with the intention of covering up a good amount of the skin. This is ideal for winter, when it’s too cold to do anything else! But if you watched TV shows like Gossip Girl (we see you, Blake Lively!), you’ll see that many of those boundaries were pushed, and that is certainly true for the prep look in a day to day sense. You don’t have to stick to strict modesty standards to rock the prep look!


To dress in preppy winter outfits, start with layering variety of the standard preppy pieces. Whether you’re throwing a sweater vest over a button down shirt or throwing a chunky sweater over top your dress, layers are your friend! And don’t limit argyle and plaid prints to tops, skirts, and sweaters – try plaid pants and plaid dresses to reverse the norm.

Think back to classic preppy looks you’ve seen – what stood out about them? Maybe it was the clean lines of the slacks, or the chunky scarves that your favorite New England-style preppy looks are rarely seen without. Maybe it was the iconically stylish winter coats, the striped shirts, or the puffy vests that look so warm and cozy. Maybe it was the quality of the pieces – how so many looked hand-knit, or high end. 

Lastly, don’t be afraid to accessorize! Big hair clips and knee-high socks are perfect ways to play up the preppy winter style. Tights go well with nearly all preppy looks, and also keep you nice and warm. A great pair of boots or oxfords is a must, which, again – we love for their practicality as well as their style. You also can lean into fun jewelry – preppy looks often favor things like pearls or gold earrings. 


Need some extra inspiration? Don’t worry – I’ve got you covered. Here are a few of my favorite preppy outfits for the winter season – scroll to get inspiration and shop for your own closet!


Rory Gilmore meets Mia Thermopolis with this look that will have you feeling like you’re back in the early 2000’s. I love how chunky and warm this sweater is, and the plaid skirt paired with Doc Martens is the quintessential fun preppy look. Pair this outfit with tights on those days that are extra-cold to stay warm and comfortable all day long.


You can’t think about cute preppy winter outfits without thinking about sweater vests. I love how this burnt orange sweater vest ties to the burnt orange of the plaid skirt, and could this trenchcoat be any cuter? I don’t think so.


Layer up in this cute and outdoorsy preppy winter look. You can’t make it through a New England winter without a good beanie, and love the fluffy pom pom on top of this one. Throw a giant scarf over your favorite black turtleneck, and stay dry with a good pair of hunter boots. This look is super cute and super practical, so I am a big fan.

Keep scrolling for more photos of my current favorite winter preppy outfit!

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