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17 Preppy-Chic Fashion Pieces to Nail the Ivy League Style Aesthetic

woman wearing red dress on street
Edward Berthelot / Contributor

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Started by It Girl Sofia Richie-Grainge, the “old money” fashion aesthetic is still going strong, the hashtag having garnered over 258k views on TikTok. One subset of the trend we can’t seem to get enough of is Ivy League style. Depicted with collared shirts, tailored pants and timeless designs — we rounded up 17 pieces from the trend so you can nail Ivy League style too.

When we think of Ivy League style, we think of the early 2000s hit show Gossip Girl meeting country club fashion. This means we’ve included things below like vests, skirts, sleek dresses, comfy cardigans and more. Each piece is classic, timeless and has a hint of sporty, preppy style that’ll make you look and feel like you’re on the steps of the Met or at an East Coast country club.

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1. Step up Your Sets: Give an update to your fashion sets game with this two-piece vest set that has a classic tailored style but a relaxed fit — $49!

2. Easy Elegance: A perfect pick for both school or lunch dates, this short-sleeve sweater dress with gold detailing is an easy way to look elegant — $42!

3. Lady of Leisure: With its laid-back yet elegant style, we picture this maxi shirt dress being perfect for Saturday afternoon cocktails in the Hamptons — was $46, now $37!

4. Timeless in Tweed: This tweed mini dress looks so elevated, no one will believe it isn’t a designer style — was $49 now $43!

5. Sophisticated in Stripes: This striped cardigan with gold buttons can be dressed up by pairing it with a dress and heels or down with some jeans and flats — was $60, now $40!

6. Perfectly Polished: With its color-block design, collared neckline and ribbed fabric, this midi dress will have you looking polished in a snap — $41!

7. Drop Dead Drop Waist: A popular dress style of today, this drop-waist midi dress looks elegant while at the same time elongating and slimming the torso — $43!

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8. Tasteful for Tennis: Nail tenniscore and Ivy League fashion at the same time with this sleeveless tennis dress from Abercrombie that features a pleated skirt, halter neck and striped hemline — $138!

9. Sophisticated Sweater: Great for pairing with trousers or a skirt for a day in this office is this French Connection short-sleeve sweater that seamlessly transitions from summer to fall — $98!

10. Tailored Trousers: Customizable to fit people of all body shapes and sizes are these tailored-style trousers from Abercrombie that come in several sizes and lengths like extra short, short, regular and long — $90!

11. Classic Capris: Not only are these low-rise capri pants easy to dress up with anything in your closet, they’re also incredibly soft against the skin — $90!

12. Perfect Pants: A number one bestseller on Amazon, these wide-leg trousers are a favorite of shoppers for their sleek and comfortable style — was $39, now $36!

13. Very Cute Vest: Wear this striped vest alone in the warmer months or over a long-sleeve top when the weather turns cool — was $36, now $27!

14. School Skirt: This plaid-style miniskirt gives a modern and stylish take on the schoolgirl aesthetic — was $110, now $70!

15. Here for the Houndstooth: A quintessential fabric of preppy style, this houndstooth blazer by Mango is the perfect way to prep for fall office fashion — $100!

16. She Means Business: Go from a presentation at the office to happy hour after with this blazer dress from Express that’d pair flawlessly with tights, heels, a headband and a clutch — $108!

17. Better Button Up: When it comes to preppy fashion, we absolutely couldn’t leave out a classic button-up top like this one from Abercrombie that goes with everything from pants to skirts to jeans and more — was $60, now $48!

Related: Decked in Linen: 18 Walmart Tops, Pants, Bottoms and Sets to Nail the Trend at Home and Abroad

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