1920 Men’s Outfits: How to Nail the Look for Your Next Event!

Last Updated: October 24th, 2023 by Kerry Wisby (Teacher-BA English Literature, 1920s & Great Gatsby Expert)

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When someone talks about the 1920s, what’s the first thing you think of? For many people, it’s flappers with their sparkling dresses and impressive styles.

You might also think of prohibition, speakeasies, infamous dances like The Charleston or Babe Ruth.

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Men’s fashions aren’t mentioned nearly as often unless the discussion is about gangsters.

What did men really wear during this period? You might be surprised at what 1920s men’s fashion was popular.

What Did the Guys Wear in the 1920s?

To understand the change in fashion, let’s look back a bit at 1900-1919 clothing styles.

The majority of men wore working-class clothing that would last them decades. Denim overalls, work boots, long johns, and thick muslin shirts.

While women’s clothing materials changed much more over the years, men’s fabrics didn’t change very much, but the style certainly did.

A great deal of what influenced men’s clothing came from the gangsters of prohibition. Even the Peaky Blinders English gang had an influence on men’s fashion.

What Did the Gangsters of Prohibition Wear?

For everyday wear, gangsters (and most other businessmen of the time) loved their suits.

Suits always included the vest, except perhaps on the hottest days of the year.

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The vest tended to button up quite high, so that even if the jacket was buttoned, you could still see the vest.

You’ll see many photos of men wearing their sports jackets open. This was so you could see their gold watch chain. There were no wristwatches yet, so it was common to wear a gold pocket watch in one vest pocket, secured by a chain that crossed the vest and was secured inside a pocket on the opposite side.

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The shoulder pads of the early 1900s were removed, and a more fitted suit jacket was worn. Pants were worn with suspenders since belts were not common yet. The fit was baggier around the waist and thighs but then tapered to a more snug fit at the ankle. Cuffed pants were also quite common as seen in many Peaky Blinders outfits.

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While most suits had all three pieces the same color, it was not uncommon to wear a vest that matched in color but had a pattern, such as checks.

It was Coco Chanel who introduced the little black dress in the 1920s, but for men, black was not as common a color unless it was worn with what were called chalk stripes, which were slightly wider stripes than today’s pinstripe suits.

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Men wore all types of colored suits as well as ties and shirts with colorful patterns. Navy blue, grey, brown, and other colors were common. While few men today would consider wearing a pink suit, it was mentioned in The Great Gatsby that Jay Gatsby wore a pink suit when he went to Tom and Daisy’s house.

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In the hottest summer months, it was not uncommon to see men wear white! Today, we might think that white suits are only acceptable for weddings, but in the heat of summer, a white linen suit looked cool and probably was much cooler than a dark blue wool suit.

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Watch The Untouchables and see how Al Capone (played by Robert DeNiro) dressed.

Like Flappers, for men, it was all about the accessories!

What Type of Accessories Did Men Wear?

You can’t talk about upper-class gentlemen or gangsters without imagining the hat, tie, suspenders, and even spats!

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It seems like everyone in the 1920s wore a hat ( see more 1920s mens hats ). Men’s hat styles included the fedora, sometimes called a Panama hat, either in straw or felt. Colored hats were also acceptable and not limited to black or brown. If you’ve ever watched the movie The Great Gatsby and observed the costumes, you’ll see that no one ever went without a hat!

Straw hats, frequently called boater hats, were also common.

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Derby’s, with their upturned edges, is a timeless design.

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What was called flat caps (now referred to as paper boy hats) were extremely popular, especially in England, among young boys and the working class.

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Collar pins or collar bars were also fashionable accessories.

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For the upper class or gangster, a collar bar was a must! Rather than holding the collar in place with buttons, the collar pin went through the edges of the collar. The ends of the collar pin could be seen, but the tie went over the pin itself. This is quite a dapper look!

A well-dressed man would also be sure that the tie and pocket square always matched. Even a plain white pocket square and a white bow tie were acceptable, regardless of the shirt color.

However, you’ll find that if the suit was plain and the shirt was a solid color, a more colorful tie or even a tie with a wild design and matching pocket square could be worn.

Matching the tie, suspenders, and pocket square might seem a bit much, but the 1920s jazz suit made these items “cool”.

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1920s Formal Wear

For more formal occasions, like today, men wore timeless styles like the tuxedo, with a longer coattail.

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It goes with a top hat.

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Double-breasted three-piece suits would also be acceptable for a formal event, especially if accompanied by a derby and some two-tone shoes, sometimes called wingtip shoes, or even spats.

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Spats were what men wore to not only cover their ankles but also make it appear that they were wearing two-tone shoes.

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For men with tighter budget, a vest and tweed jacket or coat would have to do for formal events!

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1920 Men’s Casual Wear

One of the biggest changes in men’s fashion over the previous decade was that men were no longer expected to wear the same one or two outfits for decades.

In the roaring twenties, young men could also opt to wear sportswear at home or when they were socializing with friends in an informal setting.

What we think of as a newspaper boy outfit, with short pants, boots, and a flat cap were popular even for plus-sized men and those who weren’t working for the papers!

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Golf and tennis were popular sports a century ago, so even if a gentleman didn’t play either, it was perfectly acceptable to wear the clothing.

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Loose, baggy pants were often seen by the working class, who needed to be able to freely move about as they did their work.

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Sweaters and pullovers were considered to be very fashionable at the time and a casual alternative to a suit jacket ( See Casual Mens 1920s fashion ).

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When speaking of fabric, wool, flannel, linen, tweed, and blends were still quite common. Men would choose lighter-colored clothing and linen suits for summer, leaving the wool and tweed for colder months.

You’ll find that in addition to the plain white shirt, men’s fashion favored what was called the penny collar shirt or the rounded collar.

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You’ve probably seen lots of these in the series Peaky Blinders. These were still button-up shirts, but the rounded collar could be worn without a tie or with just a bow tie for more casual wear.

Oh yes, don’t forget that short sleeves had not made a splash yet, not even for summer. On very hot days, men simply pushed up their sleeves and wore what are called arm garters to hold the sleeves up.

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What Do I Wear to a 1920s or Great Gatsby Party?

The fun thing about roaring twenties theme parties is that, even for men, there is a wide range of costumes that you can wear.

Some choices to consider would be:

The Baseball Player

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Men had very unique and identifiable uniforms in those times, so carry a baseball, a pen and autograph book, and you’re set to go as best baseballer of all time Babe Ruth!

The Dinner Party

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A stylish coat and some two-toned shoes show that you’re a sophisticated man of the time!

The Peaky Blinders Look

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Show off your English side with a flat hat and suspenders. A flask in your back pocket will complete the look.

The Mob Boss

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The Al Capone/gangster look is always a hit, and it’s fun to wear as well!

Jay Gatsby

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In a very fashionable navy blue, this suit would be the perfect choice for a Great Gatsby party.

Circus Performer

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Wouldn’t this be a fun costume? It won’t work for a formal event, but for a casual party or a costume party, we bet no one else would think of this!

Swim Suits

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This would be a super-fun costume for pool parties or lakeside parties.

Good-Time Charlie

Last, who can forget the “good time Charlie” suit?

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For young men who had little money but wanted to have fun, they could opt for a bright and colorful jacket, no vest, and still impress the ladies!

Top Tip—Accessorize!

If you keep accessories in mind when choosing an outfit, you may not need to purchase much else.

For example, if you have a formal suit, you can probably get away with just a vest, suspenders, a pocket watch, hat, and shoes.

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Wear spats if you don’t have wingtip shoes ! Two-tone sport shoes are the most authentic, but don’t be concerned if all you have are black or patent leather shoes. Those will work just fine.

Men’s Fashion Icons to Imitate

If you still need more inspiration, consider the following fashion icons of the 1920s.

Al Capone

Al Capone in 1930
Al Capone in 1930 by Chicago Bureau

This infamous gangster’s outfits were often imitated. Despite being a monster, he was a dapper dresser who knew how to show off his wealth.

Douglas Fairbanks

Douglas Fairbanks
Douglas Fairbanks by Harris & Ewing

He was a major movie star and considered to be an “All American Male.”

Rudolph Valentino

Rudolph Valentino
Rudolph Valentino by unknown author

A superstar in his time, he popularized the slick-backed hair look, frequently called the Vaselino!

F. Scott Fitzgerald

F Scott Fitzgerald 1921
A publicity photograph of writer F. Scott Fitzgerald circa 1921 by unknown author

The author of The Great Gatsby. He was well known for wearing plaid or flannel suits with contrasting ties and pocket squares.

Fred Astaire

Fred Astaire
Fred Astaire in 1919 by unknown author

The world’s most famous dancer of all time, Astaire loved more conservative looks but always dressed them up with the right accessories so he looked dashing.

Gary Cooper

Gary Cooper
Gary Cooper publicity photo used to promote the film Meet John Doe, 1941 by Warner Bros.

Another famous movie star whose clothing style was often imitated. Cooper knew how to wear a three-piece suit or the more casual pants and wide-cut blazer and still look amazing.

Look at the photos of the men above, and you’ll get a good idea about what men wore in the jazz age to look fashionable and smart.

How to Pull Off a Successful 1920s Great Gatsby Costume

You can easily buy a three-piece suit, tie, suspenders, shoes, and hat that will suit your needs, but if you’ve already got a vest or a suit, you can make it look more authentic with the following items:

  1. A Hat. This is a must-have. No one goes without a hat unless they were 5 years old or younger! You can wear just a vest, suspenders, and a flat hat1920s Mens Gatsby Newsboy Cap

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    or wear the suit with a fedora

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    or a straw hat

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  2. Shoes. Whether you wear a vest alone or the complete suit, style dictated that you wear oxfords of some kind. Plain oxfords are good for the working-class look.IZOD Men's Lewis Oxford, Dark tan, 9 M US

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    Otherwise, you should go with wingtip shoes or two-tone sports shoes.Wood8 Men's Two Tone Wingtips Oxfords Perforated Lace Up Dress Shoes (12, Black/White)

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  3. Tie/Suspenders/Pocket Watch/Pocket Square. You can choose bow ties or regular ties, but a tie is a must. Suspenders should be worn, especially if people are going to be able to see them (if you wear the three-piece suit, you can skip suspenders because they won’t be seen, but don’t wear a belt!), and the vest should have a pocket watch or, at the very least, a chain that loops from one side of the vest to the other. The pocket square should be worn if you wear a jacket.

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Other accessories, such as gloves, a coat, a tie bar, cufflinks, or a cigar can help to make your outfit look more authentic, but they aren’t 100 percent necessary.

Grooming Tips

Very little changed in the way of men’s grooming and hairstyles. Since most men wore a hat, hair was mostly hidden.

  • Hair Length
    Hair was still short to medium length. It was never so long that it would touch the collar and always cut to show the ears. Sideburns were worn a bit shorter, and the choppy jowled beard—where the sideburns, mustache, and beard were worn together like a bulldog—disappeared except for much older gentlemen.
  • Mustaches
    Mustaches were acceptable, but they were more of the pencil style—short and not at all bushy. A small, well-trimmed mustache was considered something that only the wealthy could afford to maintain as it needed attention at least weekly from the local barber. Beards were considered unsanitary and were seldom seen except, again, for much older gentlemen.
  • How To Style Your Hair
    Having neat hair, however, was a must. Whether the hair was parted or worn straight back, it was not acceptable to have flyaway or unruly-looking hair. This means that some type of pomade was worn to prevent the hair from falling forward or looking untidy. Slick your hair back using a bit of hair gel and you’ll look the part!

Final Thoughts Mens Roaring 20s Outfits

You’ll find that many men opt for the gangster look of black and white pinstripes with a fedora and perhaps pocket watches with a fake Tommy gun.

This is the most classic representation of 1920s men’s fashion, but it certainly isn’t the only one!

Consider wearing something different, such as the pink or navy blue suit that Jay Gatsby favored. Or you could wear a herringbone suit that would be reminiscent of Tom Buchanan.

There’s also the Peaky Blinders look, with the vest, long-sleeved white shirt, bow tie, and flat cap.

Alternatively, you can go all out and wear tuxedos, swimsuits, golf attire, or whatever costume strikes you as uniquely you.

You’re sure to have fun at a Great Gatsby or 1920s-themed party, so get creative, and don’t forget to learn how to do the Charleston!

1920 Men's Outfits: How to Nail the Look for Your Next Event!
1920 Men's Outfits: How to Nail the Look for Your Next Event!
Looking for 1920 mens outfits for a Great Gatsby or Roaring 20s party? We can tell you how to look dashing and authentic in minutes! Learn the secrets here.
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