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The Port Guide on How to Dress Preppy

We introduce a modern new take on Ivy League dressing.

Preppy dressing has in recent years become the punchline to many sartorial jokes, acting as polar opposite to the minimalist streetwear which serves as the status quo.

But fashion being something of a giant merry-go-round, it comes as no surprise that Ivy League cool is returning to the menswear agenda once again.

This time around, the preppy sensibility favours bold primary colours and clean, simple styling. Crucially, collegiate-inspired pieces are to be worn individually, so that one can avoid looking like an extra from Dead Poets Society.

Here, we’ve picked three pieces that, while steeped in preppy cool, have been given a thoroughly modern makeover by some of today’s most interesting designers.

Versatile Varsity

Buy Now: CALVIN KLEIN 205W39NYC varsity bomber jacket, from Farfetch
Throughout his two-year reign at Calvin Klein (designer and brand divorced in December), Raf Simons cast the mega brand with a series of all-American icons: the cowboy, the Wall Street banker, and, with this letterman jacket, the graduate.

A nod to Yale, perhaps the most illustrious of the Ivy League colleges, its royal blue front is appliquéd with authentic badges and lettering, and contrasted with calf-leather sleeves.


Resplendent Rugger

While our American cousins never really seemed to quite get rugby, they were savvy enough to adopt the jersey as their own as far back as the 1950s. Traditionally, students would wear their rugger with an open collar, perhaps layered over an Oxford shirt, but this colour block version from Phipps will most definitely benefit from being buttoned all the way to the top.


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Terrific Trousers

Buy Now: Entre Amis track trousers, from Farfetch
Crimson trousers carry so many connotations of WASPishness and Sloane Ranger-y that they’ve effectively been banished from the wardrobes of most modern men. Which is a shame, when you consider the allure of this contemporary pair from Entre Amis. Cut with a dropped crotch and elasticated drawstring waist, they’re a sportier take on the traditional chino, best worn with a muted top half.