Hey, Shady Lady!
The ribbon-trimmed raffia hat has a removable band inside the crown (to prevent irritation) and a slot for a ponytail. neimanmarcus.com, $150.
The cord around the crown can be adjusted for smaller heads, and the flexible wire woven into the brim allows for easy shaping. hats.com, $235.
Welsh is an accessories buyer turned designer whose farmer-inspired hats, like this one in red and natural straw, are hand-dyed and handwoven. helenwelsh.com, $30.
The raffia hat looks delicate, but the tightly woven crown is sturdy enough to survive time in a suitcase. hatattack.com, $68.
Coolibar's newest crushable hats are made with polyester that has a built-in ultraviolet protection factor of 50; also available in white, natural, tan, navy, black, and turquoise. coolibar.com, $30.