Preppy fashion is back, but Gen Z is giving it a whole new look. If you’ve been scrolling through TikTok or Pinterest lately, you’ve probably noticed the rise in modern preppy style: crisp button-downs, pleated skirts, polos and loafers, but reimagined with a trend-forward twist. One thing I quickly noticed after stumbling across a video explainer on TikTok—this isn’t your parents' country club aesthetic. While there’s certainly no lack of boat shoes or cardigans, Gen Z’s take on preppy fashion is all about blending timeless wardrobe staples with a street style edit. Whether you're into quiet luxury, capsule wardrobe styling or just want to know how to wear the preppy trend in 2025, this guide breaks down everything you need to know to master the look. Plus, 21 of my favorite finds that’ll help you master the look.
Gen Z Has Spoken: Here's What 'Preppy' Looks Like in 2025
Plus, preppy pieces to shop
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What Is Gen-Z’s Take on Preppy?
According to TikToker Alexandra Ballard, preppy is officially back—but it’s not just a revival of collegiate sweaters and boat shoes straight out of an ‘80s yearbook. This time around, Gen Z is putting their own spin on the classic aesthetic, mixing traditional staples with streetwear influences, oversize fits and gender-fluid styling. Think: polos worn with spacious blazers, loafers paired with crew socks and miniskirts or sweaters layered over basic tees and finished off with chunky accessories. Yes, boat shoes are still in the mix, but they’re being styled with an ironic edge—more cool-girl than country club. And while the vibe still leans polished and subtly wealthy, it feels more relaxed, inclusive and attainable. In other words, you don’t need a boarding school background or a trust fund to get the look. Instead, it’s about smart layering, tailored silhouettes and a confident, creative approach to mixing old-school prep with modern trends. Below, I break it all down.
How to Pull Off the Preppy Look
- Start with capsule wardrobe staples: Think button-down shirts, straight-leg jeans, crisp tees, fitted sweaters, polos and classic belts. These foundational pieces make recreating the preppy look effortless. Just be sure to choose tailored silhouettes over oversize ones for that clean-cut, refined vibe.
- When in doubt, tuck it in: Whether it’s a cardigan, T-shirt or Oxford blouse, a sharp tuck is key. It instantly defines your waist and adds that put-together polish the preppy style is known for.
- Don’t forget to layer: One of Gen Z’s favorite ways to amp up the preppy aesthetic? Strategic layering. Try a V-neck sweater over a tank, topped with a blazer. The combo adds depth, dimension and major style points to an otherwise simple outfit.
- Always, always, always belt everything: No joke—belts are the secret weapon of the preppy look. They cinch, shape and serve as a chic accessory. Whether you’re in jeans, trousers or a pleated skirt, a belt ties it all together. With this trend, nothing should go unbelted.
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Preppy Fashion Pieces to Shop
1. J.Crew Cashmere Relaxed T-shirt
J.Crew
As far as polished and preppy looks go, you can’t go wrong with a cashmere tee like this relaxed piece from J.Crew. It has a shorter length that’ll still tuck well into high-waist bottoms, and easy rolls at the hems for a lived-in look and cozy feel. “Soft, good cashmere can be lightweight but still warm, and just really comfortable to wear,” says a J.Crew customer. “I love the relaxed fit—it feels easy and casual, but still looks put-together. I've been wearing it on its own or layered under a jacket, and I’ve worn it with everything from jeans to dress pants.”
Fast Facts
- Size Range: XXS to 3X
Slimmer, straight-leg jeans like this COS’s Column style are the key to perfecting preppy. They’re made from a blend of organic and recycled cotton that’s quite stiff and rigid without feeling restricting—something I can attest to after I tried them on last month. Sizes are selling out quickly, so I suggest snagging a pair for yourself while you can. For sizing, I suggest sticking to your usual size, as these tend to run true-to-size, though I was able to size down to eliminate gaping at the back due to my flat bum.
Fast Facts
- Size Range: 23 to 32
Poplin shirts are a preppy essential, and this long-sleeve button-up is right on the money. It’s made with a premium organic cotton fabric that’s lightweight, crisp and soft—aka, all the things you want out of a capsule piece. What’s most impressive, in addition to that affordable price point, it’s so versatile and can really suit a number of looks, from casual weekend wear to mid-week corporate.
Fast Facts
- Size Range: XS to XL
Lioness
If you’re looking for an easy way to add depth and dimension into your outfits, try adding this striped polo shirt. It’s made from 100 percent cotton, so you can bet it’ll feel soft and breathable on your skin, and it has the classic, partial button closure at the collar.
Fast Facts
- Size Range: XXS to XXL
5. Jeffrey Campbell Yachting Day Boat Shoes
Jeffrey Campbell
If you want to lean into the literal take on the preppy aesthetic with boat shoes, be my guest. It doesn’t get preppier than this interlaced, moccasin stitching and slip-on style. “I did exactly what the reviews said and sized up a half size and they’re perfect,” says one buyer. “[They’re] very comfy pretty much straight out of the box, maybe take a little time to break in.” Sport ‘em with a chunky sock and you’re good to go.
Fast Facts
- Size Range: 6 to 11
6. Boden Eva Cashmere Crew Cardigan
Boden
No preppy look is complete without a lightweight cardigan like the classic Eva from Boden. Whether you wear it as is or tied across your shoulders, its traditional crewneck and buttoned design will make this look oh-so polished. Best of all, the soft cashmere fabric is machine-washable (yes, really).
Fast Facts
- Size Range: XS to XL
7. B-Low the Belt Milla Lether Belt
B-Low the Belt
While it may be on the pricier side, a well-made and luxurious leather belt is always a good idea, especially if you want to wear it for many years. B-Low the Belt specializes in quality belts like this Milla style. With a thick, 1.5-inch strap and wide buckle, this contemporary style encompasses a simple-yet-sophisticated design that’ll complement a number of outfits. Best of all, it comes in a handful of sizes, so you can find one that fits your hips the best.
Fast Facts
- Size Range: XS to XL
Babaton
Aritzia’s Producer blazer is my favorite closet workhorse, and one that I’ve owned for several years and worn countless times. It’s softly structed with a classic fit and darted waist to give it some shape. Use it to layer over sweaters and blouses, but make sure you leave it unbuttoned and draped over a top that’s tucked in to make it preppy.
Fast Facts
- Size Range: 00 to 18
A solid base is the key to perfecting the trend, and this Gap T-shirt, made from a soft, organic cotton, will become the most-worn item in your closet in no time. It has a straight and easy fit that’ll layer well under cardigans, V-neck sweaters and blazers. One buyer calls it “a dependable, comfortable, soft-textured and easy-fitting tee.” What’s more, it’s available in three fits: petite, regular and tall.
Fast Facts
- Size Range: XXS to XXL
This NAADAM sweater is another preppy piece you need. It has a versatile V-neck that’ll look fab over a plain tee, and it’s made from pure Mongolian cashmere that’s seriously so soft. I’m a sucker for sweaters that have ribbed details along the hem and collar—it adds an extra design element that looks sharp.
Fast Facts
- Size Range: XXS to 3X
11. Tony Bianco Martinez Leather Flats
Tony Bianco
As far as shoes go, basic, black ballet flats like this pair from Tony Bianco are ideal. They’re preppy in nature, and the flat soles will look even more elevated but just as comfortable to wear as your favorite pair of flip flops. I love how they have a thin strap at the top of the foot not just because it looks extra stylish, but also because it’ll make the shoes feel more comfortable and secure on your feet.
Fast Facts
- Size Range: 5 to 10
12. A New Day Signature Crepe Bermuda Shorts
A New Day
Now that the temps are cranking up, it’s time for shorts. These Bermuda shorts are just the right amount of preppy, with their longer inseam and pleated design. They’re made from a crepe fabric that’s intended to drape along your leg. “The fit is amazing,” gushes Cris M., a Target reviewer who bought the shorts in every color. “They're perfect because they're not see-through at all if you're wearing a thong. Also, the faux back pockets are a smart detail because nobody wants bulky pocket linings showing through.” You know the drill: Style these shorts with a polo top, belt and slinky sandal.
Fast Facts
- Size Range: 2 to 26
13. Calvin Klein Smooth Cotton Rib Sweater Polo Shirt
Calvin Klein
Speaking of polo shirts, does it get any better than this Calvin Klein number? Didn’t think so. It’s nice and fitted throughout the bodice, but made with from a breathable, ribbed cotton that’ll feel just as comfy and stretchy as a sweater. It’s a great way to add in some texture, too.
Fast Facts
- Size Range: XS to XXL
Reformation
Because it never hurts to have a few button-down options, I had to include this Reformation blouse. It’s fitted, with gathering and darts along the waist that’ll make it look like it was tailored to your measurements. Per the brand, even though it has a stretchy feel, thanks to the cotton and spandex blend, it does run small, so I suggest sizing up if you’re between sizes.
Fast Facts
- Size Range: 5 to 10
J.Crew
When it comes to the modern preppy aesthetic, Gen Z loves the look of sleek, midi skirts like this J.Crew number. Perhaps it’s because the pencil skirt is the ultimate workwear staple, letting them cosplay a 9-to-5, or maybe it’s because of the brand’s four-season stretch, which makes this form-fitting piece surprisingly comfortable to wear. Either way, it’s the perfect skirt to wear with a polo shirt and belt, thanks to the added belt loops. And the front slit will make it easy to walk in, too.
Fast Facts
- Size Range: 00 to 24
Aqua
One way to immediately make your outfit look preppy? Add a lady jacket. Aqua’s tweed jacket is refined, smart and oh-so classy with its collarless design to its gold button finishes. One customer says, “The jacket has a very elegant design, and the fabric is excellent quality with a very affordable price.”
Fast Facts
- Size Range: 00 to 24
17. Massimo Dutti Nappa Leather Woven Bucket Bag
Massimo Dutti
When it comes to ‘preppy’ accessories, handbags that are less on-the-nose and more elevated or refined are the way to go. Case in point: Massimo Dutti’s woven bucket bag, which is made from a luxe cowhide leather with a Nappa finish. The braided detail gives off picnic-in-the-park vibes while its cool design leans more fashionable. It features a deep handle strap that can comfortably fit under your shoulder, and a zip fastening to keep your belongings secure.
Fast Facts
- Size Range: one size
18. Agolde 90's Pinch Waist Jeans
Agolde
Much of the new interpretation of the preppy aesthetic takes inspo from the ‘90s, and no surprise here, but Agolde’s 90’s pinch-waist jeans were practically made for it. They’re slim-fitting, flattering, tapered. I’m a big fan of Agolde denim for a few reasons, mainly for the vintage designs and rigid cotton feel, but also for how it fits.
Fast Facts
- Size Range: 23 to 34
19. Everlane The Oversized Blazer in Buttersmooth
Everlane
This is a best-seller for a reason, folks. Beloved for its oversize fit and polished look, this menswear-inspired blazer from Everlane is taking over closets. “It’s oversized, but not so much that it looks baggy,” assures an Everlane buyer. “It's just right to pop on over a cashmere sweater when it's chilly, and it will be perfect with a tee underneath.” It comes in a handful of colorways, but I feel like this gingham finish was made for the preppy vibe.
Fast Facts
- Size Range: 00 to 16
20. Madewell Medium Perfect Leather Belt
Madewell
Behold: “The absolute most classic and quintessential leather belt,” according to one Madewell reviewer. “I love that I can wear it with dresses and pants, [and I] cannot say enough good things about this leather belt.” With a range of sizes to select from, you can bet you’ll find one made to for your body.
Fast Facts
- Size Range: XXS to XXL
Zara
Bonus: This Zara skort comes with a belt built in. I’m also a really big fan of how it wraps around, creating a flattering crossover front that breaks up the fabric. There’s even a zipper closure hidden at the side that’ll make it a breeze to put on and take off.
Fast Facts
- Size Range: XS to XL
