ILLUSTRATOR Brent Sabas
When hats ruled the world, they crowned men, finishing off their suit-shirt-shoe combos with aplomb. But then the winds shifted and men left their heads naked. Which is a shame. Like the watch on your wrist or the socks on your feet, the hat on your head is an opportunity to define who you are.
Take it from Sinatra, who, aside from looking even better with a lid on, used hats to convey how he how he felt: pushed back, at ease; pushed down, more danger. However he wore it, a hatted Ol’ Blue Eyes conveyed an untouchable coolness. Here, five essential headgear to try on.
1| The Fedora
Put on Sinatra's preferred headwear, the fedora. It fits most face shapes and, today, looks good with a suit or a T-shirt. Just remember to wear it like the crooner. Tilt the brim. And don't think about it. Fedora at AC+632.
2| The Trilby
Trilby or fedora? Inspect the margin. The trilby has a narrower brim. As with all headgear, the key is symmetry. Narrow brim on narrow faces and smaller frames. Trilby by Gucci
3| The Baseball Cap
Here, a dressed-up version of your go-to hat. The ubiquitous baseball cap hits a homerun—in ribbed suede, in an elegant forest green, with embroidered details. Upgrade now. Baseball cap by Hermès
4| The Flat Cap
At first, the flat cap was championed by Dickensian heroes. Then, it was co-opted by tweed-wearing gentleman. Today, whoever you may be, wear it. Flat cap by Burberry
5| The Bucket Hat
Where to wear the bucket hat? Near bodies of water. How to wear one that's painted in a riot of colors? With certainty (and quieter pieces). Bucket hat by Paul Smith