We fell for Mad Men styles earlier this year, and now fashion seems to be turning the clock back even further with styles from the 1920s – including cloche hats, most famously worn over flappers’ defiant bobs. Wear yours with glossy waves for the same glamorous effect.
The combination of feathers, ribbon, and a saturated jewel tone make this hat ($42) look far more expensive than it is.
This graphic plaid wool version ($95) is a more modern take.
A clean, classic option ($12.80) in wool with a no-fuss bow.
This velour felt hat ($275) by Eugenia Kim is technically a fedora…but we think its retro vibe and low brim are enough to deserve a spot on this list.