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1920s Men’s Fashion: The Ultimate Roaring 20s Style Guide

Great Gatsby Still

The 1920s and the 2020s share a number of things. Sure, there’s the Spanish Flu pandemic and our current COVID crisis. There was a time of surging economic prosperity countered by The Great Depression, which mirrors our current financial story. There are also some interesting sartorial parallels between the two decades. 

“Not unlike today, men of the 1920s looked to movie stars as their fashion icons, including Rudolph Valentino and Douglas Fairbanks,” says costume designer and fashion historian David Zyla. “But an even bigger influencer of the period was the Prince of Wales, who put a sporty spin to classic menswear, introducing brown shoes worn with a suit and other trends such as red ties, knickers, and Argyle socks.”

A more democratic take on tailored clothing was moving to the forefront. Zyla’s well-dressed stars of stage and screen, as well as the Prince, created a blend of styles that borrowed from Savile Row and the wardrobes of Princeton, Yale, and other Ivy League schools. They created the foundation that would define mid-century attire and what would become the “Preppy” look we know today. The trend was similar to today’s movement toward relaxed tailored clothing that incorporates less structure and easier movement than its predecessors. 

Athletic clothing also made its way into men’s everyday wardrobes in the 1920s, the beginnings of what we now call “sportswear.” That same Prince of Wales (later known as King Edward VIII, the royal who abdicated the throne and became the Duke of Windsor) was photographed in his crew uniform, suddenly the style became de rigeur for athletic men of a certain social standing. The trend foreshadowed the 2010’s performance fabrics moving into every item in our wardrobes. 

“The Roaring 20s was a time when fashion took a radical turn from away from the conservative, and into a less formal and regimented era of fashion,” Zyla points out. “One hundred years later we are at a similar place with fashion once again becoming de-formalized. While the idea of men dressing to show the world who they are is still alive and well, the ‘rules’ are once again loosening up.” 

When we think about men from the 1920s, we generally think of well-dressed icons, worth emulating. We asked Zyla if he had any suggestions for pieces that we could pick up to give our modern wardrobes a little bit of the era’s panache, without looking like we’re dressing for a costume party. 

“There are several items that are descended directly from the Jazz Age, and will look fresh and modern in a 2020 wardrobe,” says Zyla. “Update your go-to blazer with a double breasted one, and consider pinstripes when shopping for a new suit. This may be the season to discover the hat that suits you and your lifestyle. Add a waistcoat to a formal or informal ensemble. Whether worn casually with sneakers or as part of a suit, a higher waisted trouser is a great trend to experiment with that is reminiscent of the 1920s.” 

Beef up your shirt wardrobe with some contrast collar shirts, and don’t be afraid of stripes; the wider, the better. Men’s trends are moving toward fuller silhouettes, so look for wider lapels, higher waistlines, and relaxed fits. Incorporate elements of the decade’s heady atmosphere, but avoid the full regalia: Exaggerated silhouettes and over-the-top accessorization will have you looking less like Jay Gatsby and more like Al Capone committing a fashion crime. 

The Pinstriped Suit

Lauren Ralph Lauren Vested Suit Separates

Lauren Ralph Lauren Vested Suit Separates

Whether you need to wear it everyday because you work in finance or law; or only for special occasions like weddings and bar mitzvahs, this suit will serve you well and incorporate a bit of that 1920s gusto. We like separates because they allow us to get closer to a perfect fit without having to pay for custom. Wear it with a contrasting collar shirt, and keep neckties classic with a simple rep stripe or perhaps a quiet Art Deco pattern. 

The Double-Breasted Sportcoat

SuitSupply Havana Jacket

SuitSupply Havana Jacket

This season-spanning alpaca, linen, and wool blend combines some of nature’s own performance fabrics. The double-breasted, peak-lapeled model makes just about any guy look stronger and taller. We also like the gray melange neutral color that will dress up a pair of white jeans, look great with black or cream dress trousers, and might just convince anybody on a Zoom call that you’re not also wearing a pair of sweats.

The Waistcoat

Filson Western Vest

Filson Western Vest

This Mackinaw wool vest will provide a bit of formality to everything from a pair of jeans to a sports coat, while adding a little extra warmth for fall’s cooler days. It’s also a great piece to dress up your WFH video conference wardrobe without having to wear a full jacket. 

The Candy Stripe Shirt

English Laundry Stripe Dress Shirt

English Laundry Stripe Dress Shirt

Pair your vest with a wide, vertically striped shirt for authentic appeal. We like the black and white simplicity of this shirt, reminiscent of silent films and Hollywood glamour. As always, pay attention to proportion: Shorter or bigger men may want to stick with slimmer, trimming stripes that still have a dash of F. Scott Fitzgerald charm. 

The Higher Waist Trouser

Club Monaco Belted Pleated Trousers

Club Monaco Belted Pleated Trousers

These roomy trousers will be as comfortable as your favorite pair of sweats on those work-from-home days, but they pack a lot of style for the office or a night out with the guys. Throw them on with a crisp white shirt and that double-breasted blazer for a bit of Jazz Age style; or make them sporty with a crew-inspired tank top. 

The Hat

Scala Wool Homburg Hat

Scala Wool Homburg Hat

While a boater might be the quintessential 1920s hat silhouette, it is really only an appropriate choice for summer (pair it with that pinstriped suit at next June’s wedding circuit). Try this Homburg — a more formal, more structured version of the Fedora — to round out your Gatsby-esque wardrobe with a little attitude. It’s a very dressy look with a wool topcoat, but can also elevate a pair of jeans and a puffy vest.  

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