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



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

ADVERTISEMENT - CONTINUE READING BELOW

Comments
View More Articles About:
About The Author
Clifford Olanday
Senior Fashion Editor, Esquire Philippines
View Other Articles From Clifford
Comments
Latest Feed
 
Share
A new book reveals how showering the actor with gifts won his friendship in one of the biggest fraud cases in U.S. history
 
Share
The tech billionaire has hit a new low, being sued by the British diver he called a "child rapist". From Silicon Valley icon to daily meme-fodder, how has it come to this?
 
Share
The World Ultra Wealth Report analyzed an exclusive group of ultra high net worth individuals across the world.
 
Share
Students remember the injustice of martial law.
 
Share
 
Share
With an average pay of P9,757 per month in the Philippines, it’s no wonder Filipino nurses flock to American ERs.
 
Share
 
Share
According to the president's General Order No. 4, it is now illegal to be outside your home between 12mn and 4am.
 
Share
 
Share
Avoid looking like you're being swallowed up by fabric.
Load More Articles
Connect With Us