Blazing Ivy: A Definitive Guide to Pulling Off Preppy Style This Summer

Ivy style isn't just for fall

July 28, 2023 10:30 am
Preppy Ivy Style lookbook cutout images from the brand Rowing Blazers on an abstract pink background
We have the basic guidelines, and then some
Getty Images / InsideHook

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If you’re anything like us, you are currently feeling very strongly about two things: the fact that it is way too hot and that Paul Newman might just be the greatest dresser of old times. How can you marry these two seemingly separate ideas?

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Hopefully, you see where we’re going with this. Despite its deep ties to fall — college campuses, the Northeast, what have you — that wonderful, wacky style known as prep is just as good in the summer. With madras, linen, hemp and other materials readily available in the form of cheeky oxfords and printed pleated shorts, the sky’s the limit when it comes to pulling off preppy style this summer.

What Is Preppy Style?

Contrary to what TikTok might have you believe, prep has less to do with old money and boats than you might think. Born out of college campuses in the mid-20th century, prep finds ground in-between rugged functionality and a serious formality, buoyed by pleats and polos. Come summertime, prep focuses on imbuing a button-down feel (and arguably as important, prioritizes the physically cool), all while maintaining an air of sophistication that comes with webbed belts and blazers. Dock sneakers, terry cloth, popovers: it’s all there to play with. Below, we’ve pulled together three looks to inspire you to preppy heights. Below, how to dress preppy this summer.

How to Dress Preppy in 2023:

The Smart Trackstar

Seeing as how the style dabbles in both the sartorial and the sporty, a high-low combination is always a proper prep move. Pairing a breezy top and blazers with a pair of (smart) shorts is perfectly acceptable, if not encouraged, granted you pick the right pieces. Elevated athleisure — like the Falmouth Shorts from Tracksmith, our favorite running boutique — makes all the difference.

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The Madras Master

There’s an old saying: if it ain’t broke, don’t fix it. We wholeheartedly agree — a breezy madras popover and chino shorts are a preppy look as old as the style itself, and for good reason. That doesn’t mean you can’t improve on the formula though, so try unique accessories or crisp new deck sneakers to spice up an otherwise classic outfit.

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The Yacht-Bound

Ivy style is inherently entrenched with boating culture (ever heard of a guy named JFK?). But even if a personal yacht is not currently in the cards, emulating nautical nature is highly recommended for a killer summertime ‘fit. Huge pants and a rugby polo go together like apple pie and ice cream, and it wouldn’t be a hot prep summer without a pair of boat shoes in play.

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