It’s the defining look of all-American fashion. It’s the most enduring and influential menswear code of the 20th century. It’s arguably the movement that invented the very concept of smart-casual dressing (so you know what to blame the next time a dress code dilemma paralyzes you in front of the mirror).

Yes, preppy style is the evergreen fashion trend that’s been in—in one form or another—for the best part of 70 years. Growing from the elite Ivy League schools of the 1950s and 1960s, preppy fashion became the uniform of style icons like JFK, Paul Newman and Miles Davis.

Prep is also what the empires of Ralph Lauren and Tommy Hilfiger are built on—easy-to-wear staples like color-block polo shirts, cable-knit sweaters, button-down oxford shirts and chinos. And such is the versatility of the look, it’s influenced everything from Italian tailoring to skatewear, hip-hop style to Japanese workwear.

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