Rihanna and Hailey Bieber Make This '80s Teen Trend Feel So 2023

Put some prep in your step.

You don’t have to be a devout follower of fashion trends to have major feelings about certain styles. Those of us that grew up in the Y2K era find the resurgence of low-rise jeans and going-out tops polarizing, while other throwback trends, like the preppy look, tend to ebb and flow in and out of style with ease. This is due in large part to decades of evolution, pop culture iconography, and increased availability thanks to American brands like Ralph Lauren and Tommy Hilfiger that have allowed the look to maintain relevance over the past several decades.

First rising to prominence in the early 20th century, the original “preppy” style was a subculture that emerged from the elite preparatory boarding schools and Ivy League universities found in New England. As more women entered the halls of higher education in the ‘50s and ‘60s, the trend evolved to include more female-focused designs like twin sets, collared shirts, and athletic wear, both on and off the field. However, the preppy style we know and love today first gained prominence in the 1980s, thanks in part to The Official Preppy Handbook, the tongue-in-cheek bestselling tome that chronicled the rise of khaki pants, plaid blazers, and cable knit sweaters worn everywhere and with everything.

Related:13 Ways to Wear a Tennis Skirt Off the Court

Today’s iteration of the preppy trend is, thankfully, a bit less rigid, and a lot more fun. Style stars like Rihanna and Hailey Bieber have been spotted wearing the trend unironically, having embraced items like wide-leg trousers, colorful Loewe polos, and of course, sporty sneakers. And guess what? Even though these preppy wardrobe staples trace their roots to the ‘80s, today’s version of the preppy look is anything but antiquated, and — crucially — easily accessible for everyone.

Whether you’re nuts for knits, all about athleisure, or simply obsessed with matching sets, there’s a modern interpretation of the preppy style that is sure to catch your eye. Scroll on for some of our favorite recent street style inspo, and prepare to make a few impulse purchases. Don’t worry, given the legacy of the preppy look, these pieces are sure to maintain their place in your future wardrobe, too.

Easy A

Embrace the preppy style’s roots in academia with items like a pleated skirt, crisp white button-down, and knit athletic-inspired sweater. Bonus points for oversize, retro glasses.
SHOP SIMILAR: Coach Varsity Cardigan ($225)

Polo and Plaid

A preppy sleeveless collared shirt and plaid skirt get a 2023 update with bright colors and combat boots. Or, take it in a totally different direction with a headband and ballet flats. 
SHOP SIMILAR: Amanda Uprichard Dixon Skirt ($148)

Classic Cableknit

The cableknit sweater is a classic preppy piece. Give the trend a twist by creating a rich, monochrome look with a darker color and matching trousers. For extra credit, don't forget the white collared shirt underneath!
SHOP SIMILAR: Buck Mason Alpaca Cable Crew ($238)

All of the Pink

Pink is for everyone when it comes to nailing the preppy look. We especially love how this style star paired her punchy pink suit with a fluffy, frothy sweater and petite purse.
SHOP SIMILAR: By Malene Birger Mohair and Wool Sweater ($750)

Need for Tweed

Preps are mad for plaid, and tweed comes in at a close second. Combine the two in an unexpected color like the yellow set seen here for a 2023 take on the classic style. 
SHOP SIMILAR: Veronica Beard Bryne Tailored Check Jacket ($698)

Denim Does It

The ‘80s introduced denim into the preppy equation, and we must admit we’re grateful. Give your go-to straight-leg jeans the preppy glow-up they’ve been missing by styling them with a black leather belt, boots, and a blazer. Extra credit for including Wayfarer sunglasses, too.
SHOP SIMILAR: Everlane The '90s Cheeky Jean ($110)

Wrap a Cardigan Around Your Shoulders

If there are two things that true preps love, it’s Kelly green and a loosely-tied cardigan. Here’s a monochrome version that incorporates these two staples but with a bright, bodycon twist making the look thoroughly modern. 
SHOP SIMILAR: Enza Costa Silk Rib Tank Midi Dress ($195)

Add a Pantsuit

The easiest way to incorporate the modern preppy look into your wardrobe is by pairing a brightly colored two-piece suit with a matching sweater. Tie it casually over your shoulders to complete the look, and don’t forget to have fun with your accessories.
SHOP SIMILAR: Mango Modal-blend suit blazer ($140)

Try Ripped Jeans

This look incorporates the basics of preppy style, but it’s anything but boring. A cropped collared shirt and oversized ripped jeans look perfectly polished under a navy blue blazer. Plus, any prep will tell you that a petite Hermès Kelly bag goes with everything.
SHOP SIMILAR: Reformation Noah Shirt ($128)

Play with Pastels

Pastels are super preppy but can often look a little too sweet. Mix and match pastel versions of oversize suiting separates for a more androgynous take on the trend, like Karolina Kurkova does here in Thom Browne. Coordinated socks are optional but strongly encouraged.
SHOP SIMILAR: Thom Browne socks ($90)

Try a Knit Set

Take the preppy look to the wild side by pairing a brightly colored knit set with an oversize suede jacket and animal print heeled boots. Unexpected, but totally into it. 
SHOP SIMILAR: H&M rib-knit skirt ($25)

Layer a Blazer Over a Sweater

Like Olivia Palermo, we’ll take any excuse to wear a chunky turtleneck sweater under a blazer. Although this combo seems to only work for a few days out of the year, it’s worth investing in these quality wardrobe staples to wear separately as well.
SHOP SIMILAR: Zara blazer ($190)

Coordinated Colors

Twinning with your bestie is totally prep-approved. We love how this duo coordinated their color story, complete with contrasting bags and matching pink pumps. 
SHOP SIMILAR: Veronica Beard heels ($177)

Button Up in a Shirtdress

A belted cotton shirtdress is both preppy and timeless. Pair a khaki-colored dress with brightly colored heels and accessories for a look that will never go out of stile.
SHOP SIMILAR: Shoshanna Clark Ruched Sleeveless Midi Dress ($460)

Off-Duty Athletic

With the oversized chinos and New Balance sneakers, this outfit is close to entering dad core territory. However, the neutral colors and duo of knit tops place this ensemble firmly in the preppy camp. A true prep would wear Ray-Bans, but we love how these sporty shades take this look into the 21st century. 
SHOP SIMILAR: Everlane the Relaxed Chino ($118)

Put a Hat on It

A Kelly green preppy dream ‘fit! We love how the textured baseball cap, mini bag, patterned socks, and tasseled loafers set this look apart. 
SHOP SIMILAR: Lele Sadoughi Raffia Baseball Cap ($85)

Pair a Mini and a Cardi

You may not have gotten away with wearing a khaki cargo mini skirt this short in high school, but that doesn’t mean it won’t fly now. We love how this “vintage” preppy look combines classic preppy staples with a ‘90s feel, including chunky knee-high boots, and a mini denim designer bag.
SHOP SIMILAR: Boots / Skirt

Go for Varsity

Take it from this look: A varsity jacket goes with literally everything. Lean into the trend with chunky retro-looking loafers, and keep it modern with a mini bag. 
SHOP SIMILAR: Mother varsity bomber jacket ($298)

Try Tennis Whites

Tennis, anyone? This head-to-toe white look is an easy way to ace the preppy trend, whether or not you’re hitting the court. 
SHOP SIMILAR: Dress / Shoes

Tie on a Scarf

Accessories take a basic jeans and button-up outfit over to the preppy side via white sneakers, a silk pastel scarf, and a campus-worthy backpack. 
SHOP SIMILAR: Silk scarf ($55)

Layer on Neutrals

Layering luxe materials (jewelry included) is most certainly a modern take on the preppy trend. Just remember to stick to the basic building blocks: A button-down, sweater, tailored trousers, and sporty sneakers are all you need to nail the look.
SHOP SIMILAR: Quince long-sleeve linen shirt ($40)

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