The New Preppy Aesthetic: Outfits That Are Polished, Playful, and Totally 2025

Think of this outfit as the perfect blend of Blair Waldorf polish and TikTok-era prep. The result? A collegiate-inspired look with a flirty, modern twist. It nails the schoolgirl aesthetic with sporty, preppy undertones that feel effortlessly wearable for everyday life. To amp up the charm, don’t be afraid to go a little kitschy—tall socks or tights add the perfect finishing touch.

When putting this look together, steer clear of tight fits or dated sweater patterns. Instead, opt for oversized, cable-knit styles to balance out the mini length of your skirt. The Quince Australian Merino Wool Cable Sweater Vest is a cozy, elevated pick that gets it just right and is on discount if you sign up for Quince emails. Layer it over a crisp button-down—Gap’s Organic Cotton Poplin Big Shirt is our top choice (and worth grabbing in more than one color with this Gap promo code).

For the skirt, we recommend going with a true tennis skort that moves with you. The Athleta Match Point High Rise Pleated Skort is a standout—it’s equal parts functional and fashionable, with a gorgeous spin and flattering fit that rank it high among our best athletic skirts. Score it for less with this Athleta promo code. (Image credit: @danielaboho)

This preppy-meets-prairie outfit delivers major picnic-core vibes with just the right touch of rugged charm. The star of the look is a chore-style barn jacket—equal parts farmhand and fashion-forward. Layer it over a gingham dress for a soft, feminine base, then ground the whole outfit with a pair of sporty sneakers. It’s the perfect example of the “wrong shoe theory” done right, adding contrast that feels intentional, not costume-y.

We’re loving the New Balance 327 sneakers for this vibe, they’re sporty, stylish, and come in all the classic NB colorways (shop them with this Macy’s promo code). Want to take it a step further? Top off the look with a worn-in baseball cap for that effortless, borrowed-from-my-dad finish.

Ready to shop this '90s-inspired look? Pin the Tuckernuck Catlin Showerproof Jacket and the Tuckernuck Jolene Dress to your style board, or better yet, snag both with this Tuckernuck promo code. (Image credit: @immillieholmes)

If we could live in one preppy outfit all summer, this would be it. This Y2K-inspired combo is clean, sporty, and effortlessly polished—no costume vibes here. A well-fitting polo dress is the key to nailing the look, giving you that timeless preppy feel with a modern edge.

We’re obsessed with the Ralph Lauren Striped Polo Dress, which blends old-school charm with a contemporary silhouette. Pair it with a crisp white sneaker—we recommend the Cariuma OCA Low Canvas Sneaker for comfort and cool-girl style (and yes, you can grab them at a discount with an Anthropologie promo code). Finish it off with a structured top-handle bag like the Mansur Gavriel Candy Hobo to elevate the whole ensemble from weekend casual to main-character chic. (Image credit: @danastargazertruitt)

If you’re a fan of Blair Waldorf-level polish, this timeless combo is a must. It’s preppy to the core, super versatile, and works just as well for a casual Friday as it does for Sunday brunch. Want to give it a coastal spin? Just sub in boat shoes for the loafers and you’re set.

The key to pulling this off is a crisp button-down. We love the Everlane Relaxed Oxford Shirt—it’s structured, comfortable, and endlessly layerable. For that signature over-the-shoulders look, try the Quince Boyfriend Sweater—its soft cotton knit and just-right slouch give off perfectly preppy energy. As for shoes, you can’t go wrong with trendy loafers from G.H. Bass, Rothy’s, or VIVAIA, but we’re especially into the VIVAIA Francesca Loafers right now. They add a little height and a lot of polish. Grab them with this VIVAIA coupon for a deal. (Image credit: @sweetsavleigh) 

This outfit delivers peak “quiet luxury” energy—a blend of modern prep, fashion-editor polish, and a hint of '90s grunge. It’s the kind of look that says you know all the style rules—and when to break them. Keep the palette tonal or neutral to lean into that old-money aesthetic while letting the textures and layers do the talking.

The key here is structure and proportion. Pair your cable knit with tailored wide-leg trousers like the Reformation Mason Pant, which brings just the right amount of volume while still looking put-together. Top it off with a thoughtfully cut trench coat—J.Crew’s New Icon Trench hangs beautifully without overpowering your frame. Snag your perfect outerwear piece with a J.Crew promo code or grab the trousers with a Reformation coupon. 

As for sweaters, look for slightly cropped or boxy styles to balance the sleek lines of your suiting and trench. The Quince Cropped Cable Sweater is our favorite—it’s cozy, classic, and effortlessly preppy. (Image credit: @chloejade_story)

This outfit is a pitch-perfect blend of '80s prep and Y2K nostalgia—with a 2025 twist. It’s playful, polished, and just the right amount of unexpected. Few preppy aesthetic outfits walk the line between posh and cheeky quite like this one.

The star of the show? The Polo Ralph Lauren Cropped Rugby Shirt with bold, primary-color stripes straight out of an '80s yearbook. It’s got retro charm and modern fit down to a science—and you can grab it with a Saks Fifth Avenue promo code. Pair it with a neutral pleated mini for balance; we love how the Lulus Pleated Mini Skirt keeps the focus on the top. Use a Lulus promo code to shop it smart.

To finish the look, socks and Mary Janes are a must. While there are plenty of trending flats that bring an updated Y2K energy, nothing completes the vibe quite like Rothy’s The Square Mary Jane. Use a Rothy's discount code and treat yourself to a pair that feels both nostalgic and now. (Image credit: @jeanne_andreaa)

This look is garden-party ready with a dash of edge—perfect for polished girls who like their preppy with a twist. The sweetheart vibe of a pink plaid blazer layered over a sheer tee or floaty blouse feels feminine and nostalgic in all the right ways. We’re especially into the Talbots Lovely Tweed Blazer—an heirloom-worthy piece with major main-character energy. Try a Talbots promo code to score a sweet deal on this timeless jacket.

To keep things feeling current, try pairing the blazer with wide-leg pants or relaxed denim. But if your inner ‘90s girl is begging for a Clueless moment, a matching mini skirt totally fits the brief. And don’t forget the accessories—nothing completes this look like a mini bag. We love the Staud Mini Moon Bag for its subtle ‘90s silhouette with a modern update. Scoop one up with a Bloomingdale’s coupon code. 

Finally, skip the heels and slip into something a little more effortless. Cap-toe ballet flats give off that signature Chanel energy without trying too hard. The VIVAIA Tiana Flats—with their almond toe and sweet bow—are a chic dupe that stands on their own. (Image credit: @lavinia.td)

Let’s pack for the Hamptons—even if it’s just in our daydreams. This chic nod to East Coast prep works everywhere from the office to weekend brunch, offering timeless polish with just the right amount of ease.

If you're new to tie-neck blouses, opt for something soft and airy rather than overly structured. We’re loving the Banana Republic Georgette Cross-Tie Trapeze Top, it’s flowy, breathable, and delivers that effortless elegance we’re after. Don’t forget a Banana Republic promo code when you’re ready to shop. Not into the tie detail? No worries—swap it for a crisp pick from our roundup of the best white button-down shirts. 

To keep the look elevated but unfussy, go with high-rise, straight-leg ankle jeans. The Levi’s Ribcage Straight Ankle Jeans are a go-to, offering a tailored silhouette that fits the preppy brief without feeling too buttoned-up.

Accessories should stay simple and chic. Think open-back gold hoops and just a hint of shimmer. We’re tying it all together with the Tuckernuck Champagne Shimmer Lame Marina Puffy Headband and the Tuckernuck Natural Annie Bag—both refined, playful, and perfectly preppy. (Image credit: @jeanne_andreaa)