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A Brief History of the Flat Cap (and How to Wear One Today)

Kangol Wool 504 flat cap

The flat cap — also known as the ivy cap or driver cap — has quietly become one of the most popular alternatives to the baseball cap. But this humble cap has a history stretching back more than 500 years. Here’s a brief history of the flat cap, and how to wear one today.

Origins: five centuries of the flat cap

Kangol Wool 504 wool flat cap

The flat cap’s roots trace back to England and Ireland as far back as the 1400s. Working-class British and Irishmen wore rough wool flat caps, while finer versions in silk and cashmere topped the heads of upper-crust golfers and country-clubbers. A 16th-century English law even required men and boys to wear a wool cap on Sundays to support the domestic wool trade — helping cement the cap as everyday headwear.

Crossing the Atlantic

The cap arrived in America with the British and Irish immigrants who came through Ellis Island. It soon took on two new identities: the “driving cap,” associated with taxi drivers around New York and New England, and the “ivy cap,” named for its popularity at the Ivy League schools of the Northeast.

The modern flat cap

Bailey Ormond tweed ivy cap

Today the flat cap sits right at the smart-casual sweet spot — a step up from a baseball cap, but more relaxed than a fedora. It pairs perfectly with tweed, wool, and flannel for fall and winter, and lighter cotton and linen for spring and summer. Whether you call it a flat cap, an ivy cap, or a driver cap, it signals effortless, put-together style.

Get the look: the classic Kangol Wool 504 is the definitive flat cap, while a tweed Bailey Ormond Ivy Cap nails the heritage look. Browse our full range of flat caps, ivy caps & driver caps — with free US shipping on orders over $100.

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