September 25, 2023

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Shop 7 Preppy Style Staples for 2023

Preppy style isn’t just an aesthetic; it’s an entire visual universe with a popped collar. We hardly have to mention “prep” for you to assemble the preppie look in your mind’s eye: a pearl choker worn with a rugby shirt layered over a pleated skirt, sitting pretty in a golf cart on the rolling hills of a Westchester course or tied up with a flowing ascot tie in the back of a 2001 convertible Jetta cruising home from Middlebury for spring break.

The hallmarks of Ivy League style are very much back in fashion, as evidenced by BAZAAR’s series exploring the return of preppy style. The shopping list for getting the look, however, needs a few updates and a personal style disclaimer. Modern prep style, be it sexy, sporty, or mischievously twisted, hasn’t consigned its earliest staples away. But it is introducing entirely new pieces to the lexicon while reviving old favorites and embracing individual interpretations above all. Academic-adjacent staples like loafers and sweater vests are an invitation to layer with library-chic abandon; sportswear chinos are baggier and more utility-inspired; understated nylon bags toe the line between then, now, and whatever aesthetic shift comes next.

Most importantly, the prep pieces fashion has embraced once again aren’t being advertised in a Heathers formula for followers to copy. The seven essentials for embracing the new prep can be worn however you want, whenever you want.

The Loafer

GH Bass 1936 Willa Strap Weejuns Loafer
Credit: GH Bass

Midinette All Calf Loafer

Belgian Shoes Midinette All Calf Loafer
Credit: Belgian Shoes

Jordaan Leather Loafer

Gucci Jordaan Leather Loafer
Credit: Gucci

From Margot Tennenbaum in her GH Bass Wejuns to a cadre of editors, stylists, and Upper East Siders in Gucci Jordaans, loafers are one of prep’s universal accessories. These smart shoes have been remixed and re-remixed in infinite ways (lately, with lug-sole and platform soles), but it’s silky-smooth leather and shiny hardware accents will forever stand the test of time; preferably, with a little crew sock layered underneath.

The Nylon Bag

Re-Edition 2000 Mini-Bag

Prada Re-Edition 2000 Mini-Bag
Credit: Prada

Felix Nylon Shoulder Bag

Staud Felix Nylon Shoulder Bag
Credit: Shopbop

Large Le Pliage Tote

Longchamp Large Le Pliage Tote

Lisa Birnbach, author of The Official Preppy Handbook, told BAZAAR, “Preppy is that Prada nylon bag that was sitting in the back of your closet for the last 10 years. Some newer bags are great and terrific but they’ve got quilting and pearls that are so fussy—and that is the antithesis of preppy.” You heard it from the high priestess of preppiness herself, it doesn’t get more classic than a Prada re-edition. Nylon bags from Longchamp and Staud also possess the essential unfussy factor preppies love.


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The Ballet Flat

Leather Ballerina Flats

Miu Miu Leather Ballerina Flats
Credit: Bergdorf Goodman

Black-Owned Brands

MM6 Maison Margiela Black-Owned Brands
Credit: Shopbop

Ava Leather Ballet Flats

The Row Ava Leather Ballet Flats
Credit: Net-a-Porter

Prep ran (in ballet flats) so “ballet-core” could soar (on TikTok). The uncomplicated shoe helps you float through the day with the poise of a ballerina and the unaffected air of an Ivy League trust-fund baby. But here’s some ways of styling from the recent runways that’s likely never occurred to them: with chunky socks and leather hot-pants, or with a tiny skort and a gingham puff-sleeve blouse.

The Tennis Necklace (or Bracelet)

Moss Round Cut Necklace

Dorsey Moss Round Cut Necklace
Credit: Dorsey

Classic Sapphire Tennis Bracelet

Monica Rich Kosann Classic Sapphire Tennis Bracelet
Credit: Monica Rich Kosann

18k White Gold Diamond Choker Necklace

Anita Ko 18k White Gold Diamond Choker Necklace
Credit: Bergdorf Goodman

This country club staple isn’t behind wrought-iron gates and under a polo shirt anymore. Casual, unpretentious styling is on the rise and renewing our interest in this prep classic: You’re as likely to see icy tennis necklaces in a tangle of chains and pendants as you are to see them sparkling by themselves.

The Pleated Skirt

Tartan Check Pleated Wool Mini Skirt

Miu Miu Tartan Check Pleated Wool Mini Skirt

Now 65% Off

Credit: Bergdorf Goodman

Striped Wool Mini Skirt

Thom Browne Striped Wool Mini Skirt
Credit: Net-a-Porter

Spliced Plaid-Print Belted Mini Skirt

Chopova Lowena Spliced Plaid-Print Belted Mini Skirt
Credit: Bergdorf Goodman

Pleated skirts have long been a hallmark of private school dress code etiquette, but the newest iterations are all about breaking the rules. Miu Miu makes a handful in varying hem lengths (short, super short, and super, super short). Chopova Lowena makes the alt-punk girl version with a thick leather carabiner belt and a mishmash of prints and plaids. And Thom Browne makes a gray version with his signature white stripes that would probably go over well at boarding school, until you style it with a black leather lobster bag. Either way, any of them will help you live out your rebellious teen dreams as an adult.

The Chino Pant

The Relaxed Chino

Everlane The Relaxed Chino
Credit: Everlane

Monte Pants

Mara Hoffman Monte Pants
Credit: Shopbop

Wide-Leg Chino Pant

Polo Ralph Lauren Wide-Leg Chino Pant
Credit: Ralph Lauren

The prep revival isn’t just bringing chinos back; it’s reclaiming them. Leg shapes are getting wider (just like jeans), pockets are getting deeper and more cargo-adjacent. Even throwing them together with basic clothing like a plain white T-shirt, a directional belt, and one of the best loafers above, these casual-cool pants feel miles away from the school and pharmacy uniforms where they spent most of the 2000s—but they’re still functional.

The Sweater Vest

Rose Striped Wool Vest

Molly Goddard Rose Striped Wool Vest
Credit: Net-a-Porter

Francis Pullover Vest

Alex Mill Francis Pullover Vest
Credit: Alex Mill

Aniene Fair Isle Vest

Dôen Aniene Fair Isle Vest
Credit: Net-a-Porter

Sweater vests are the versatile little layer that every corner of modern prep seems to embrace, from dark academia (with a button-down, blackwatch tartan pleated skirt, and chunky loafers) to grandpa-meets-Gen-Z-chic (with a contrasting striped shirt and chinos) to sexy yet preppy (with low-rise denim and nothing underneath). They’re connected to the hallowed outfits of prep’s origins, but they’re just as likely to be worn by present-day style icons like Bella Hadid and Harry Styles.

Fashion Commerce Editor

Halie LeSavage is the fashion commerce editor at Harper’s BAZAAR. Her style reporting covers everything from reviewing the best designer products to profiling emerging brands and designers. Previously, she was the founding retail writer at Morning Brew and a fashion associate at Glamour.

Headshot of Tara Gonzalez

Tara Gonzalez is the Senior Fashion Editor at Harper’s Bazaar. Previously, she was the style writer at InStyle, founding commerce editor at Glamour, and fashion editor at Coveteur.

Headshot of Jaclyn Alexandra Cohen

Senior Fashion & Accessories Editor

Jaclyn Alexandra Cohen is Harper’s Bazaar’s Senior Fashion & Accessories Editor. Outside of the office she can be found downtown with her twin sister, figure skating somewhere or on the hunt for the perfect striped top. Follow her on Instagram @jaclynalexandra