New Era make the best structured baseball cap and have supplied MLB teams since 1934 — the quality that comes from being the official supplier of professional sport is evident in every detail. The 9Forty fits universally with its adjustable back strap, the structured crown maintains its shape rather than collapsing, and the curved brim follows the right profile without curling unevenly. Available in hundreds of colourways. The cap against which all others are measured.
Lock & Co have hatted the Royal Family and British gentlemen since 1676 — longer than the United States has existed — and the Hatta is their British flat cap done properly. Robust tweed in classic British patterns, structured brim that maintains its shape in rain, satin lining that slides easily over hair, and construction in England using materials sourced from the same mills for generations. Smart enough for a day at the races, casual enough for a walk in the country. The hat you hand down eventually.
The Italian hat brand worn by everyone from film directors to jazz musicians and the original against which every other felt hat is measured. A Borsalino is handmade in Alessandria, Italy using a production process that takes weeks per hat — the felt is blocked, shaped, steamed, and finished by craftspeople who've spent careers learning the trade. The grosgrain ribbon is exactly right, the proportions are classical, and putting one on makes you understand immediately why people have been buying them since 1857.