Fashion

3 Hats You Can Definitely Pull Off

These furry creatures show you how to do it
IMAGE Paul Del Rosario
ILLUSTRATOR Brent Sabas
Comments

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



ADVERTISEMENT - CONTINUE READING BELOW

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

ADVERTISEMENT - CONTINUE READING BELOW

***

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



ADVERTISEMENT - CONTINUE READING BELOW

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

ADVERTISEMENT - CONTINUE READING BELOW

Comments
View More Articles About:
Recommended Videos
About The Author
Clifford Olanday
Associate Editor, Esquire Philippines
View Other Articles From Clifford
Comments
Latest Feed
 
Share
What would you do if you were in one of these true horror stories in the office?
 
Share
The three rulers of Manila, Rajah Sulayman, Matanda, and Lakandula co-ruled as equals.
 
Share
Apo Whang-Od agreed to a collab with a New York-based streetwear company.
 
Share
If he gets to keep his German Shepherd co-star from AppleTV+'s See, it'll be because she's cool with it.
 
Share
 
Share
Philippine superstitions and folklore were the perfect weapons against rebels.
 
Share
The revamped website aims to be a one-stop platform for the many travelers looking to explore the country's 7,641 islands.
 
Share
I spend an hour rustling up a nutritional meal, but it only takes five seconds for all hell to break loose
Load More Articles
Connect With Us