1920s Mens Fashion: Classic Sheik Style

1920s mens fashion is "classic" in the same way a Austin-Healey 3000 Mk III is classic. We won't ever see them roll off the line in the same way, but they remain iconic and beautiful for the aficionado. 

The impact the 1920s had on modern men's style cannot be overlooked. From suits to sportswear, men wore well-made and well-tailored clothes that have stood the test of time.

Esquire Magazine chose a half dozen male 1920s icons for their Top 75 Best Dressed Men of All Time:

  • Al Capone - #3
  • Albert Einstein - #25
  • Humphrey Bogart - #35
  • F. Scott Fitzgerald - #45
  • William Faulkner - #65
  • Fred Astaire - #68
1920s Men's Fashion- Douglas FairbanksDouglas Fairbanks looks sharp in the classic men's fashion of the 1920s

Carey Grant just missed the list since his career didn't start until 1932. Michael Corleone from The Godfather Trilogy was born in 1920 and comes in at #21.

That is a lot of star power and great mens fashion. 

The Rapid Change of Men's Fashion

Mens fashion of the 1920s showed a a sharp and unique contrast to those of the previous decades. 

At the end of WWI, men came home to find their closets full of clothes that were outdated. The soldiers returned to the "Edwardian" and Victorian wardrobes they had left before the war.

These clothes didn't reflect the progress of technology, marketing, and individualism that marks the 1920s as a unique decade in American history.

The Re-invention of Menswear

Look through the photographs of the 1920s and you will see the progress of menswear in the 1920s.

Men became "fashion conscious" due in part to the quickly developing marketing departments at retailers like Montgomery Wards and Sears, plus Hollywood movies displayed dashing leading men like Rudolph Valentino, Douglas Fairbanks, Al Jolson, and Charlie Chaplin.

The Sacque Suit

Though during the early parts of the decade men still wore the very structured slim sacque suits that had been popular with gentlemen since the mid-1800's.

These suits were ill-fitted from uncomfortable fabrics, they weren't good at maximizing the shape of a man's body. The shoulders were narrow, the sleeves were often too short, the trousers also didn't lend themselves to comfort.

An Era of Classic Style

Men's Fashion - Fred AstairFred Astair, Dapper As Always

If you think of men's style in the 1920s you have to think of a very masculine look. Ernest Hemingway, Charles Lindbergh and F. Scott Fitzgerald were some of the most iconic men ever.

These men were defined by their amazingly well-tailored suits.

Defined shoulders, narrow hips, quality durable fabrics like leather, wool and cotton were typical of men's clothes. Classy ties and accessories brought the look together. 

1920s Mens Fashion Trend: Loosen Up Those Tight Pants

Up until the 1920s, loose pants were considered no-nos for men, loose fitting pants were reserved for the ladies.

This was in large part to Valentino's role in the film The Four Horseman of the Apocalypse.

The 1920s are famous for the debauchery and the progress that was made during the decade. 

1920s mens fashion - loose fitting pantsLoose Fitting Trousers of 1920s mens fashion

Building a Gentleman's Aesthetic

1920s mens fashion wasn't the same in the Roaring Twenties as it is today, of course. Men wore top hats with tails for formal occasions like the theater or weddings.

Beneath their tailored suit, a white dress shirt and a starched removable white collar.

1920s Mens Fashion Trend: High Polish Shoes

Shoes were a big part of the style. Oxfords were typically worn with formal evening wear.

The classic black and white or black and tan wingtip show was also very popular for formal occasions. 

1920s Mens Shoes: Black and White WingtipsBlack and White WIngtips


For men in the Roaring '20s there were many popular hat styles to choose from.

  • The Fedora
  • The Trilby
  • The Porkpie
  • Classic Top Hat
  • The Bowler
  • Newsboy Cap
Al Capone in a Fedora

Al Capone in a Fedora and Tie: The #3 Best Dressed Man In History 

Of course, the Fedora and Trilby are still worn by stylish men with the attitude and guts to pull it off. After all you can't wear a hat well if you don't have confidence in it. 

Men's Accessories of the 20's

From the classic bowtie to the classic standard length tie, men accessorized well in the 1920s.

Pocket watches, ascots, scarves, were all popular items for 1920s mens fashion depending on climate and culture.

Plus Fours and Knickerbockers

Plus-Fours, sixes, eights, etc. all referred to how many inches below a young mans knee his trousers hung.

This look was popularized by professional 1920s golfers like Walter Hagen and Bobby Jones.

The craze developed in England, at Oxford University, and evolved into a style worn by men for much longer than you'd expect. Amazingly, they were worn until the 1950s.

1920s Mens Hairstyles

1920s Men's HairstyleTypical Men's Hairstyle of the 1920s

Simple is the word to describe men's hair in the 1920s. Cut short and fading up to a longer top that could be styled neatly using hair tonic or grease and a comb.

Men still style their hair very much in the same way. Leonardo Dicaprio, George Clooney, and many others famously wear hair that could be straight out of the 1920s