Old Men Wearing Pocket Squares

William Faulkner, writer and Nobel Prize laureate


 
Pocket squares have a very rich history dating back to pre-biblical times. Throughout the early and mid-twentieth century, pocket squares were a necessity in every man’s wardrobe but their popularity started to fade as dress-codes and prevailing styles became more casual and laid-back.

 

Today, pocket squares are undergoing a resurgence as men are becoming more aware and particular about how they dress and classical styles, patterns, and cuts are coming back into mainstream fashion.

 

In truth, a suit or sport jacket has a pocket for a reason and the reason is to put a square into it. Without a pocket square the suit looks incomplete and “naked”. One can find many guides on how to fold a pocket square and how to pair a pocket square with a tie.

 

The purpose of this article isn’t to educate on how to wear the accessory but rather to remind everyone that the accessory needs to be worn. Some of the most important life lessons are taught to us by our parents and grandparents. Therefore, here are a bunch of old men to remind us all that wearing a pocket square is not being “fashion-forward”. Rather, it is simply abiding by well-established rules of classical, timeless men’s dress.

 

Winston Churchill, Prime Minister of the United Kingdom - wear pocket squares

Winston Churchill, Prime Minister of the United Kingdom

Sean Connery, actor and producer - wear pocket squares

Sean Connery, actor and producer

Sammy Davis Jr., musician, comedian, and actor - wear pocket squares

Sammy Davis Jr., musician, comedian, and actor

Rainier III, Prince of Monaco - wear pocket squares

Rainier III, Prince of Monaco, with wife Grace Kelly

Charles, Prince of Wales - wear pocket squares

Charles, Prince of Wales

Miles Davis, jazz musician and composer - wear pocket squares

Miles Davis, jazz musician and composer

Louis Armstrong, trumpeter, composer, and singer - wear pocket squares

Louis Armstrong, trumpeter, composer, and singer

Humphrey Bogart, actor - wear pocket squares

Humphrey Bogart, actor

Gay Talese, writer and author - wear pocket squares

Gay Talese, writer and author

Gary Cooper, actor - wear pocket squares

Gary Cooper, actor

Fred Astaire, dancer, actor, and choreographer - wear pocket squares

Fred Astaire, dancer, actor, and choreographer

Frank Sinatra, singer and actor - wear pocket squares

Frank Sinatra, singer and actor

Fats Waller, jazz pianist and composer - wear pocket squares

Fats Waller, jazz pianist and composer

Edward VIII, Duke of Windsor - wear pocket squares

Edward VIII, Duke of Windsor

 


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