This reconfigured fedora by Eugenia Kim features a wool felt construction, matching band, and unique, geometric crown.
$425, Eugenia Kim, online only
Fedoras are back in fashion, and Rag & Bone’s simplified version is one of the best out there. Their Floppy Brim Fedora sports dark wool and a leather accent band, making for a surprisingly timeless look.
$195, Rag & Bone, online or at NeimanMarcus
Panama hats are always a safe bet. Madewell X Biltmore’s version is constructed with oversight by Eric Lynes, head of a century-old haberdashery — ensuring a good fit and solid style. Who says you can’t wear white after Labor Day?
$58, Madewell, The Westchester, White Plains
Straw might not scream C-suite, but Banana Republic’s Braided Straw Hat provides the ideal late-summer insouciance. The on-trend material and relaxed construction make it an easy way to add a bit of style when running between boardrooms.
$39.50, Banana Republic, multiple locations and online