Your Guide to 1920s Men’s Fashion: Get the Gatsby Look

Welcome to the 1920s!

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A booming economy and flourishing arts and culture set the scene for a decade of indulgence and fun that became known as ‘The Roaring Twenties’.

The automobile was bringing people together like never before, while the new music of Jazz was pushing the boundaries of what music could be.

Then there’s the fashion.

1920s mens fashion peaky blinders

Fashion of the 1920s has become increasingly popular in recent years, partly due to the huge success of TV and film features like Peaky Blinders, Downton Abbey and The Great Gatsby.

Read on to find out how to create a classic 1920s men’s style.

Roaring 20s Outfit

The most outfits of the 20s you’ll see most commonly recreated today are broadly: the pinstripe suits made famous by gangsters, practical workwear of the lower classes, Great Gatsby-esque outfits, or a rough n’ ready Peaky Blinders look.

For the majority of men, suits were the day to day attire. Almost always, a suit would be worn with a hat: styles ranged from the fedora to the homburg, to a round bowler. In the summer months, the Panama hat was the headwear of choice.

1920s Shoes

Before the 1920s, cap toe lace-up boots were worn by working men and gentlemen alike for almost all occasions. They were sturdy and comfortable while looking smart enough for formal occasions.

During the 1920s though, Oxford shoes began supplanting the lace-up boot as the shoe of choice for the contemporary male. They were essentially the same as the previous lace-up boots, except they were missing the section around the ankle which made them ‘boots’ rather than ‘shoes’.

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Other shoe designs that became popular in the 20s were the Wingtip Oxfords, two-tone tennis shoes, and slippers.

1920s Suit

The suit was the essential element of the 1920s man’s wardrobe. Unless you were a blue-collar worker, sportsman, or teenaged, suits were the go-to look for all occasions.

1920s men's fashion

In the main, suits were made with thick wool, wool tweed, mohair, wool flannel, or corduroy. These materials meant that the suits were somewhat heavier than today’s suits, but lighter than those that came before them.

When it came to jackets, they were double or single-breasted with 3 to 4 buttons. 1920s suits were characterized by high lapels, something very unique to this era. With all the buttons done up, the jackets would completely cover vests, showing just the collar and necktie.

The color of the suits were usually dark and light browns, medium blues, dark greens, and greys. For the more daring gentlemen, a pastel pink suit was a great choice for attracting attention while remaining within the rules of fashion. 

Interestingly, the classic black suit, often donned in gangster films depicting the era, is a Hollywood myth. Black suits were strictly for mourning and cash-rich gangsters would have worn only the most fashionable suits of the day, not funeral wear.

Great Gatsby Outfits

Leonardo DiCaprio
CANNES, FRANCE – MAY 15: Actor Leonardo DiCaprio attends the Opening Ceremony and Premiere of ‘The Great Gatsby’ at The 66th Cannes Film Festival Festivals on May 15, 2013 in Cannes, France

After seeing Leonardo DiCaprio and the rest of the star-studded cast live out the lives of the 1920s rich and famous in The Great Gatsby, it’s hard not to want to emulate the sophisticated styles of these socialites. Here’s how you can do it.

The Suit

Gatsby would have worn a well-fitting (not baggy) medium brown, grey, or light blue suit. Suits were always buttoned up high in the 20s, so pick a jacket with 4-6 buttons, ideally with peak or notch lapels.

The Vest

Gatsby would have always taken great care to ensure that his vest and trousers matched. Not all had the money to own a matching suit, but as a very rich man, Gatsby would have. The vest should be single or double-breasted with 6 buttons up the front.

The Pants

It’s exceedingly difficult to find men’s pants today that sit as high as those of the 1920s. Amazingly, they tended to fit just below the rib cage. Your best bet is to find classic fit men’s suit pants or golf pants. Although belts were becoming more common, Gatsby would have worn button-on suspenders in the main, so go for them.

The Shirt

When it comes to the shirt, there’s only one option. A French cuff shirt with cuff links is the only way to go. For the collar, go pointed or round club. White collars were a popular look, as were solid color shirts with matching collars. Feel free to go for vertical stripes or subtle checks, too.


The Shoes

1920s mens fashion

Another big change for men during the 1920s was a move from sharp, pointy shoes to more roomy designs. Instead, Oxfords were made with round or wide box tips to give the toes more room. In the second half of the 20s, Oxford designs began to get more creative, incorporating reptile skins like alligator or embossed leather.

Gatsby was a fan of the two-tone shoes which were gaining popularity in the 1920s. Brown, white or grey would work very well. Alternatively, go for a more old-fashioned cap-toe lace-up Oxford, or even dark brown wingtips.


The Hat

Men were rarely seen hatless in the 1920s. Though the movie does indeed show many hatless heads, this is due to the face obscuring problems of hats rather than historical accuracy. Fedoras, bowlers, derbys, and even newsboy hats will all work well for a Gatsby look.


The Tie

polka dot tie
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Feel free to choose a necktie or bowtie. The patterns that were popular at the time were wide diagonal stripes, polka dots, deco patterns, and paisley. Be sure to wear a matching pocket square to complete the look.

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