Roaring 20s: How to Bring 1920s Men's Fashion Back (2024)

Roaring 20s: How to Bring 1920s Men's Fashion Back (1)

100 years ago, men were wearing three-piece pinstripe suits and flapper girls weredoing the Charleston at the local speakeasy. Oh, how times have changed! But what could be classier than fashion pulled straight from one of Jay Gatsby's parties?

Now that we're entering a new era of the '20s, 1920s men's fashion can, and should, make a roaring comeback. If you're looking for ways to pay homage to the fashion of the day 100 years ago, read on for everything you need to know.

1920s Men's Fashion: An Overview

When it comes to teaching men's fashion in the 1920s, it's all about status and employment. You could tell how much a man earned just by looking at him.

Worker's Wear

A working-class man in the 1920s might be spotted in a shirt and tie with jeans held up by suspenders. Paired with a jacket, the look was finished with a flat cap. Mix-matched suits were commonly worn by working-class men. Without the proper means, they had to take what they could find at discount stores and donation bins.

On the job, overalls were the name of the game for the average blue-collar worker. Large pockets on the front of the overalls were used to carry tools and the bottom of each pant leg was often cuffed.

Business Wear

The typical 1920s businessman wore a three-piece suit with a hat to match. Unless you were a tradesman, athlete, or student, your suit would constitute your everyday attire.

Men's suits were typically made from heavy materials like wool, tweed, flannel, or corduroy. Suit jackets were worn atop vests that fastened over a dress shirt. When buttoned, a man's jacket would completely conceal the vest, which was a departure from the styles ofprevious decades. Men always woreneckties or bowties and folded a handkerchief neatly in their breast pocket.

As for designs, a classic 1920s suit could be found in pinstripes, wide stripes, plaid, or checkered patterns. They were rarely black and more often colored in greys, blues, and varying shades of brown.

Formal Wear

1920s formal wear drips with elegance and class. Top hats were worn with dinner jackets and paired with matching flat-front pants that were high-waisted and often hit above the ankle. These were great clothes for short men, as pants were not expected to reach the tops of one's shoes, even when standing.

Shoe spats were pieces of fabric that buttoned up the side and fastened around the ankle. Fanning out in a trumpet shape, they covered and protected a man's classic black patent leather Oxford shoes.

Recreating the 1920s Look

What would be a better time than the present to bring back all the best fashions of the 1920s? Here's what you can look for if you'd like to dress in the Roaring Twenties style.

Tops

If you want to find ways to recreate 1920s men's fashion, consider trying on a fewsweaters. Cardigans that button up the front as well as one-piece pullover sweaters both grew in popularity in the 1920s. Pieces with large, knitted collars or turtleneck designs were enjoyed for their added warmth in the winter.

But don't forget what goes underneath! Men's dress shirts were always worn and came with round, club, and pointed collars. They were often a mix of different striped or diamond patterns and were complemented by a necktie.

Bottoms

Do you think low-hanging pants and skinny jeans were strange trends? Trousers and pants went through equally odd phases in the 1920s. Except, instead of dangling or super skinny styles, trousers were high-waisted and extra wide.

It all started with the knickerbocker, later shortened to the knicker. Knickers were wide-legged pants that hugged the waist and stopped tight around the knees. These morphed into different variations based on length, called plus-fours, plus-fives, and so on. The number represented the length at which the knickers hit below the knee. For example, plus-fours stopped four inches below the knee.

Knickers were eventually banned in Oxford, England, spurring the creation of the Oxford bags. These trousers were excessively wide, so much so that they could be worn over top of a pair of knickers. Though sinched at the waist, Oxford bags could be as wide as 44 inches around!

Hats

Though top hats may be considered outlandish nowadays, you can still harken back to the 1920s with other caps. Flat caps have grown in popularity in recent years and were a staple of the 1920s working-class look.

The fedora is another popular hat from the 1920s and has that classic gangster look. To bring out your inner detective or channel the charm and charisma of Humphrey Bogart, try a wide-brimmed fedora.

Other hats that reflect the style of the day include the rounded derby hat, the straw boater hat, and the ready-for-summer Panama hat. Grab the style that speaks to you and you'll be bringing the 20s back with accuracy and flair!

Accessories

No 1920s-era outfit is complete without the right accessories. And men had a lot of them! Consider a cane or walking stick to take with you on your way to work. Styles range from those with curved handles to those with straight tips.

Suspenders were a must for the period, keeping trousers perched high on the waist. For a night out, pair your outfit with a patterned bowtie, gloves, shoe spats, and a dazzling pair ofmonogrammed cufflinks.

Bring Back the 20's in Style

In the 1920s men's fashion was, for the most part, simple and effortlessly stylish. Though we may not opt for the same heavy wool and tweed fabric that was popular then, we can still bring back the '20s vibe by dressing in similar styles.

Want to do something simple? Find a classic newsboy flat cap and you're halfway there! Getting ready for a Gatsby-themed Roaring Twenties party? Try on a three-piece suit and a homburg hat to look and feel like you've jumped out of the history books.

If you want to bring the best styles of the 1920s back this decade, check out our collection ofpatterned dress shirts.

Roaring 20s: How to Bring 1920s Men's Fashion Back (2024)

FAQs

Roaring 20s: How to Bring 1920s Men's Fashion Back? ›

Men used to wear tuxedos, well-tailored pinstripe suits, raccoon fur coats, silk shirts, handkerchiefs, black patent shoes made of leather, spats, and bow ties in the 1920s.

How to dress like a man in the 1920s? ›

Men used to wear tuxedos, well-tailored pinstripe suits, raccoon fur coats, silk shirts, handkerchiefs, black patent shoes made of leather, spats, and bow ties in the 1920s.

What was the main way men's fashions changed in the 1920s? ›

The 1920s were also a time for casual dress. As menswear became less regimented, leisure clothes and sportswear made their debut. This meant sweaters, plus-fours, and other wide or baggy pants, workwear pants, jumpers, caps, and an array of accessories people could wear to express themselves.

What were 4 characteristics of men's fashions in the 1920s? ›

1920s Fashion for Men

Suits: Three-piece suits with wide lapels and high rise cuffed trousers in stripes, plaid, tweed, and wool suiting. Shirts: Narrow stripe dress shirts with white or matching collars. Colored or plaid two pocket work shirts. Pants and Breeches – Long pants, work overalls and golf knickers.

What did lower class men wear in the 1920s? ›

A working-class man in the 1920s might be spotted in a shirt and tie with jeans held up by suspenders. Paired with a jacket, the look was finished with a flat cap. Mix-matched suits were commonly worn by working-class men.

What should a man wear to a Great Gatsby party? ›

In summary, the best Great Gatsby outfits for men should consist of being well groomed, dressed in a nice suit and accessorized with items like bow ties, pocket squares and boater hats.

What did gentlemen wear in the 1920s? ›

The 1920s saw the rise of the tux, complete with shawl or peak lapels and satin. They were often worn with white waistcoats and bow ties. White tuxedos were a symbol of wealth, so men wanting to make a statement sometimes opted for one of these.

What did upper class men wear in the 1920s? ›

Eveningwear for upper class men consisted of slim-fitting trousers, a waistcoat, a white shirt with an attached winged collar, a white bow tie and white gloves. Eveningwear etiquette also required a tailcoat that would be worn with a top hat and black patent leather shoes.

What was the biggest fashion trend in the 1920s? ›

Also known as the flapper, the look typified 1920s dress with a dropped waist and creeping hemlines that could be created in economical fabrics. Coco Chanel helped popularize this style (Fig. 1) and was a prominent designer during the period.

Who were the best dressed men of the 1920s? ›

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.

What did mens pants look like in the 1920s? ›

As for trousers, the first half of the 1920s featured narrow pant legs, and they gradually widened as the decade progressed. College men took the new wide-leg styles to heart and began wearing “Oxford bags,” which had leg widths up to 16 inches!

What did men wear during Great Gatsby? ›

Gatsby would have worn a well-fitting (not baggy) medium brown, grey, or light blue suit. Suits were always buttoned up high in 1920s fashion for men, so pick a jacket with 4-6 buttons, ideally with peak or notch lapels.

How were men portrayed in 1920s? ›

Men were labeled as the authoritative figure in a majority of households in 1920. Men were pressured to work as long and hard as possible during the weekend due to the mother not having a source of income. A father's responsibility was to make the income.

What shoes were popular in the 1920s? ›

The most popular shoe of the roaring 20s was the pump with a modest 2inch (5cms) heel. Basic slip-on pumps, 18th century inspired colonial shoes, walking oxfords, and boots made up the other shoe styles.

Why did everyone wear hats in the 1920s? ›

A hat could protect a person from the rain, the wind, or the soot from local smokestacks. Long before SPF 55 was readily available, hats were also the single biggest protector from the sun. The sweatband could catch beads of perspiration before they got into your eyes.

What did male aristocrats wear? ›

The luxurious outfit that men from the 18th century nobility would wear, the habit à la française, is composed of a coat, waistcoat, and breeches. It also included a pair of silk stockings, a jabot, a linen or cotton shirt with decorative cuffs, and a cravat (a neckcloth).

What did men wear to speakeasies? ›

A black full dress suit or tails, worn to the opera or private parties. Cream dinner jacket or navy/black tuxedo, worn to nightclubs and evening parties. A black or navy daytime business suit, worn to less expensive seats at concerts, to the movies, or out dancing.

How to dress like a 1920s gangster? ›

Gangsters in the 1920s meant business, and that showed in how they dressed. They looked sharp and important in their signature 3-piece suits (dark-color or striped) with short suit jackets and a double cuff shirt.

What is Gatsby wearing on the day of the tea? ›

Gatsby dresses for the event in a "white flannel suit, silver shirt, a gold-colored tie." His clothes, like his parties, his house, and his car, are an overt reminder of his newly earned wealth. It is as if he wants to make sure Daisy does not miss the fact that he now has that one thing that eluded him before: money.

Did men wear fur in the 1920s? ›

Throughout the decades, the fur coat has always been a staple in the closets of the best dressed gents. While fur coats for men were certainly around in the 1900s, the fashion probably peaked in popularity in the 1920's and early 1930's, before it was revived in the 1950s and 1970s.

What did men wear to bed in 1920? ›

Men's 1920s Nightshirts

For going to bed, men had four choices: Nightgown, Pajamas, Underwear, or Nude. The traditional nightshirt, nightgown or nightrobe was ankle length, long sleeved, with a button up military collar or V neckline made of cotton, wool, linen, or flannel.

How did men dress 1919? ›

Evening wear was dominated by dark tailcoats, worn with a waistcoat and trousers. However, the less formal tuxedo was also an acceptable form of evening wear. Men sported quite a range of suits, sportswear, and evening wear for every occasion (Fig.

What is a 1920s mens hat called? ›

Fedora Hats for Men Wide Brim Panama Hat with Classic Belt 1920s Gatsby Panama Fedora Hat Cap.

What slang was used in the 1920s? ›

Crab: Figure out • Crate: Car • Croak: To kill • Croaker: Doctor • Crush: An infatuation. Crushed out: Escaped (from jail) • Cush: Money (a cushion, something to fall back on) • Cut down: Killed (esp. shot?) Policeman Page 7 1920s Slang 7 o A collar or an arrest.

What is the style of peaky blinders? ›

The historical Peaky Blinders, operating in Birmingham, England from the late 1880s to the early late 1910s, were known for their style, which included expensive ties, prominent brass buttons on their jackets, bell-bottoms, and their eponymous peaked caps, from which they derived their name.

What were three trends in the 1920s? ›

Flappers

With pencil-thin eyebrows, bee-stung lips, and short hemlines, the style of starlets like Clara Bow has become iconic. In addition to their dress, the public smoking, drinking, dancing, and liberal stance on sex of these young women scandalized polite society.

What colors were popular in the 1920s? ›

What colors represent the 1920s? Neutral colors were popular in the 1920s, such as light pink, off-white, green, and pale gold for women, and light blue or green for men. These colors reflected the cultural emphasis on airy, less-restrictive clothing in the 1920s.

What brands were popular in the 1920s? ›

And the brands launched in the 1920s were no less luminary: Kenco (1923), Brylcreem (1928), Durex (1929), Fyffes (1929), as well as impulse brands Smith's crisps (1920), Star Cigarettes (1923), Fry's Crunchies (1929) and Lucozade (1929). These treats no doubt helped distract from post-war depression.

What was attractive in the 1920s? ›

Beauty in the 1920s featured an androgynous look for women. They wore bras that flattened their chest and wore clothing that gave them a curve-less look. Women even shortened their hair, leaving behind the long-held belief that long hair signified beauty and desirability.

Who wore jeans in the 1920s? ›

Jeans & American West

Modern jeans began to appear in the 1920s, but sales were largely confined to the working people of the western United States, such as cowboys, lumberjacks, and railroad workers.

Where did men sagging their pants come from? ›

Origin. The style was popularized by hip-hop musicians in the 1990s. It is often claimed the style originated from the United States prison system where belts are sometimes prohibited and there can be a lack of appropriately sized clothing. As a result, their pants would sag.

What did men wear before jeans? ›

Breeches. Men in this time period did not wear long pants. Their pants, called "breeches", came to just below the knee. They had a button fly and pockets and often buttoned at the knee as well.

When did pants become masculine? ›

By 1820 trousers as they are known today had come into general use among men. Since then they have been the basic style of dress for men, varying from the narrow cut to the extremely wide Oxford bags of 1924. Within Western society, trousers were long regarded as masculine apparel.

Why does Gatsby throw his shirts around? ›

Gatsby throws all his shirts on the table because he is excited. He has pined for Daisy since he left her so many years ago. He has been constantly chasing the American Dream in pursuit of wealth, positioning himself to be good enough for her.

Did The Great Gatsby wear a hat? ›

The main characters, Jay Gatsby(Leonardo DiCaprio), Nick Caraway (Tobey Maquire) and Tom Buchanan (Joel Edgerton) wore boater hats with a variety of colorful patterns. But many of the additional characters wore fedoras in straw or felt, newsboy caps and flat caps.

What was the dress code for Gatsby party? ›

In keeping with the theme of the Roaring Twenties, all Great Gatsby Party guests are required to follow the evening's dress code. Men are invited to come in black tie, while women are requested to arrive in flapper fashion.

What were 3 characteristics of the 1920s? ›

Roaring Twenties: Flappers, Prohibition & Jazz Age.

What is toxic masculinity in the 1900s? ›

Since the early 1900s, toxic masculinity has held a narrow and repressive description of manhood that's defined by sex, status, and aggression. Men had to uphold the role of being the protectors, breadwinners, providers, and overall care and control their families.

How is masculinity portrayed in The Great Gatsby? ›

Tom Buchanan appears to embody maleness. He possesses all the qualities that the dictionary links to masculinity: he is “strong; robust; [and] powerful” (The New Webster Encyclopedic Dictionary 519). However , despite Tom's status as a masculine ideal, Nick depicts him as a man in search of his self.

What kind of jewelry did they wear in the 1920s? ›

1920s Inspired Jewelry

Flappers frequently wore Art Deco-inspired brooches on their fur collars and cloche hats, as well as long continuous strands of pearls or round beads, gem-studded bracelets and lariat necklaces with tasseled ends. Wide bracelets, both cuff and memory wire styles, were popular.

Did 1920s wear boots? ›

It has been said that after wearing boots and long dresses for so long, women in the 1920s wanted to show off their feet. One shoe that achieved this – the 'T-strap' – was perhaps the most popular shoe of the Roaring Twenties.

Did they wear boots in the 1920s? ›

Women used to wear lace-up boots all the time, but in the 1920s, a more casual shoe style emerged with the Oxford. Strappy heels were worn with evening attire. Lace-up Oxfords were practical and sturdy with a low heel.

Why did men stop wearing fedoras? ›

One of the biggest reasons for the loss of hat-wearing is likely that we now have better control over our indoor climate than we used to. This is also why men can now go in and out of doors, sometimes wearing fewer than two layers of clothing, and why things like gloves and scarves aren't as popular as they used to be.

Why did men not wear hats inside? ›

Throughout history hats identified social standing and removing a hat was a gesture of respect. In the "old days," men took off their hats in Christian churches, when they entered someone's home, when greeting a boss, and always in the presence of a lady.

Did men wear fedoras in 1920s? ›

Fedora hats were the casual headwear of the 1920s. The most popular hat of the decade was definitely the fedora. While most people today would look at a man wearing a fedora as being quite formally dressed, at the time, the fedora was a casual alternative.

What did men wear to Royal Balls? ›

This would consist of the same white ruffled shirt, white tie, white stockings and shoes as civilians. The waistcoat and breeches would be white or off- white. The uniform coat would be made of superfine wool and would vary depending on the country, branch of the service, rank and regiment.

What did lower class men wear? ›

Men probably wore linen undergarments, woolen hose or breeches, a linen shirt or smock, and a woolen coat or tunic. On his feet he would have worn leather shoes, around his waist, a leather belt from which he could hang a bag or other tools.

What did men wear before suits? ›

Courtiers Began To Dress Differently

At this point, courtiers began to dress in sober tunics and fitted breeches, in sombre tones which echo the tones of most modern business suits. Shades of tunics and breeches worn included grey, navy and taupe. These primitive "suits" became more tailored over time.

What did men wear during The Great Gatsby? ›

Gatsby would have worn a well-fitting (not baggy) medium brown, grey, or light blue suit. Suits were always buttoned up high in 1920s fashion for men, so pick a jacket with 4-6 buttons, ideally with peak or notch lapels.

How do you dress like an old gentleman? ›

Try khaki slacks, a sweater vest, and bow tie to go as an old man.
  1. Wearing a full suit is another option, if you have one. You could also check a second hand store for a vintage suit.
  2. If you want to look like an old man in pajamas, wear a matching pajama set with a robe and slippers.

How to look like a vintage man? ›

Vintage Men Dressed Better–Here Are 10 Keys to Their Style!
  1. Black Tie.
  2. Shoes.
  3. Socks.
  4. Trousers.
  5. Dress Shirts.
  6. Odd Combinations.
  7. Neckwear.
  8. Hats.
Apr 10, 2022

What makes a man old fashioned? ›

You respect yourself – body and mind.

A proper old-fashioned man treats himself as an old-fashioned man would. He makes sure to look good, smell good, taste good, and – most importantly – feel good. Being on the top of your game mentally and physically is the only way a true old-fashioned gentleman wishes to live.

How can a man look vintage? ›

Look for bold vintage prints in faded colours (sun-beaten is more subtle) and wear the Cuban-feel shirt with tailored chino shorts and espadrilles or linen trousers and loafers for a smarter feel.

Why do mobsters wear pinky rings? ›

Especially in the United States, pinky rings also developed an association with criminal activity. Grifters were thought to wear such rings, sometimes to provide their associates with a source of funding for their funeral expenses in case of their death, as were made men in the American Mafia.

What is 1920s attire? ›

Also known as the flapper, the look typified 1920s dress with a dropped waist and creeping hemlines that could be created in economical fabrics. Coco Chanel helped popularize this style (Fig. 1) and was a prominent designer during the period.

What did men dress like in 1922? ›

Throughout the decade, men wore short suit jackets, the old long jackets being used merely for formal occasions. In the early 1920s, men's fashion was characterized by extremely high-waisted jackets, often worn with belts. Lapels on suit jackets were not very wide as they tended to be buttoned up high.

How did men dress in 1793? ›

The men wore plain, dark clothing and short unpowdered hair. During the Terror of 1794, the workaday outfits of the sans-culottes symbolized Jacobin egalitarianism.

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