The bowler is arguably the iconic hat of the 20th century. Also known as the coke or the derby, it was developed in 1850 in London for Thomas Coke, the Second Earl of Leicester. The bowler was seen as an alternative to the more formal top hat and the soft felt hats worn by working-class men. By the early years of the 20th century, the bowler became a symbol of the bourgeoisie.

Sporting styles of the 1920s contributed to the popularity of soft felt hats like the fedora and the homburg. The homburg was loosely based on Tyrolean hunting hats and often featured feather trim. This literal “feather in your cap” added panache. Further dazzle was provided by the silk pocket square and coordinating necktie.

As sportswear became increasingly influential, the 1920s also saw the emergence of the spectator, a type of shoe that developed from traditional brogues and oxfords. Originally worn as a golf shoe, the spectator soon became popular for casual wear off the green. Trendsetters such as the Prince of Wales wore spectators, as did many young women. The vogue for sporting dress led to the demise of the rigid collars of the early 1900s, in favor of the button-down or soft, spread collar.