1
THE BUCKET
This ultracasual accessory isdesigned
to maximize sun protection, while two metal eyelets on each side keep you cool. Lacoste $35
Consider teaming it
with capris, shorts, or anything sporty.
GILLIGAN
2
The Trilby
Once the rich man’s fedora, the trilby has a shorter brim (angled upward in back) and a lower crown than its counterpart J. Crew $40
Top off a linen or lightweight suit for a timeless silhouette.
FRANK SINATRA
3
The Panama
Originally from Ecuador, this traveler’s companion can be rolled up and stuffed into a weekend bag. Tommy Bahama $108
This versatile fair-
weather hat can be
dressed up or down.
TEDDY ROOSEVELT
4
The Porkpie
Popular with the jazz crowd, the porkpie was typically made of brown or green felt and has a cylindrical crown. Rag & Bone $125
You’ll hit the
right groove with a laid-back ensemble.
LESTER YOUNG
Photogrpahs by second row (From Left): Woolrich Woolen Mills, Marni, Steven Alan, Issey Miyake; third row (From Left): Everett Collection (4)