Preppy, Gossip-Girl-Inspired Back-to-School Outfit Ideas

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Can you believe it’s already August? There are only a few weeks left before school starts again, at least for those of us who are on the semester system, and with the beginning of another school year, it’s customary to start preparing our back-to-school wardrobe! 


With the recent reboot of the mega-popular television series Gossip Girl on HBO Max, I’ve been obsessed with the preppy, private school look again, just like I originally was more than ten years ago when the original series first aired. Read on to see some of my favorite looks that will be perfect for the back-to-school season! 


1. Tweed Overcoat, Black and White Uniform, and Over-the-Knee Boots

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There’s nothing classier than a tweed overcoat, which first became a fashion industry staple following the popularity of Chanel’s take on this specific article of clothing. Typically, I shy away from tweed, since it can be difficult to wear it in a way that seems age-appropriate, but when paired with a private school uniform, it helps to add an air of sophistication to an otherwise youthful look. Try opting for a darker-colored jacket, since it’ll work for all seasons. While it may be common to wear loafers with such a classic preppy look, I’d opt for over-the-knee boots, just to add a rebellious flair to the whole ensemble. 


2. Knit Vest, Loose Button Up, and Skater Skirt

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If it’s a bit warmer where you live, try opting for a loose button-down instead of a tweed coat. To make the look more fun, try adding a knit vest on top. Not only does this give off an interesting textural contrast, but the whole look is also preppy without trying too hard. You can always wear


3. Slouchy Cardigan, Untucked Button-Down, and Tights

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This outfit is my personal favorite because of the slouchy cardigan. I love the oversized fit since it makes me feel extra cozy, and it helps to soften up the preppiness of the button-down, uniform skirt, and ankle boots. When choosing a cardigan, make sure to pick color schemes that work with your uniform, but don’t shy away from flashy details like intricate buttons or exaggerated sleeves—these add a fun and unique touch to your outfit that’ll make it distinctly yours. 


There are so many fun variations, and you can always mix and match any of the outfits above to create new looks! That’s one of the things that I love most about the preppy style—it’s so easy to put together chic and effortless looks that just look stylish without seeming like you’re trying too hard. What’s in your back-to-school wardrobe?