1920s Mens Fashion Style Guide - A Trip Back In Time (2023)

If you’re looking for the golden age of men’s fashion, you don’t have to look further than the 1920s. This decade was a time when fashion took a turn from the conservative, old styles into a new era of fashion.

Although the early 20s didn’t see much in the way of new fashions, when you think of the dapper suits and dresses of the 20s, many of those styles were products of the later part of the decade.

Regardless, many of the most popular men’s fashion styles today are still modeled from the fashion of that decade.

Fashion to that point had been some of the same suit styles over and over, with no casual clothing anywhere to be found. The 20s saw many radical suit styles as well as the introduction of casual and sporty dress for men. The formality of dress lessened, and clothing encompassed more choice and more fashion forward options.

If you are looking to up your fashion game, you can’t go wrong with mastering 1920s style. It was an effortless, classy era of men’s fashion that paved the way for many of our more modern styles. So let’s start from the top.

1. Dress shirts

The dress shirt is an essential staple of 1920s men’s fashion. Tall, white detachable collars reigned king in the world of fashion thanks to their ease of laundering.

In the mid-1920s attached collars became the preferred standard. Attached collars offered a softer feel in comparison to the rigid and uncomfortable nature of detachable collars. For inspiration, see Nucky Thompson from the TV show Boardwalk Empire.

Collar styles at the time included both round edge club, spread and pointed. Though, you should know that spread collars were greatly influence by the introduction of the wide Windsor tie knot. Soft point was reserved for button down shirts. Wing tip collars were a common sight amount even wearing with bent over points to allow for bow ties.

Shirt cuffs included French and double.

Collar pins which were quite popular during the 1920s, were placed through eyelet holes.

See the best dress shirts for men here.

2. Hats

Upper Class: Top hat and homburg hat.
Middle Class: Bowler Hat, trilby hat, and fedora.
Summer (Middle and upper class): Straw boater
Working-Class: Flat cap and newsboy cap.

Hats in the 20s depended largely on which class you belonged to. Remember the movies about page boys and factory workers from that time? Working class men wore the “page boy” style hats, called newsboy caps or flat caps.

If you were solidly middle class, you would have owned a fedora hat. Those fedoras were holdovers from the gangster styles, working class or middle class men coming into sudden money, but keeping the style associated with their own class.

Fedora style was also accompanied by bowler hats, another 20s movie staple. These ubiquitous styles belonged to fashion conscious middle class fellows, looking to shake up fashion. It was the first time that middle class citizens were able to use material goods to express who they were. Fashion became a statement for the first time for regular people.

During summer vacations, you would wear a straw hat.

If you were upper class, you retained the top hat style. Another type of upper class hat is something called a Homburg, a felt hat with a single crease at the crown and a rolled edge. If you look at pictures of past presidents, a few wore this style even up to the 1950s.

Regardless of style, the one common denominator is wearing a hat. Mastering 20s style is essential to bringing back the class and dignity of that era of dress. Although hats have fallen out of favor in recent years, wearing a well-fitting, well-made hat will make or break your look.

3. Suits

Listen close: another secret to mastering the style and grace of 20s fashion is the suit. Men’s fashion today is a combination of athletic clothing and ill fitting jeans. You need to step far away from such casual menswear and begin to take pride in your suit fittings.

Suits were a central part of the 20s man’s fashion. Although it retained some of the classic fashion of the past, changes in cut and material lent it a modern, jazz-age flair. 1920s suits have influenced menswear ever since, from the 1940s zoot suit to tighter-fitting modern styles.

Formal suits still came in black as the standard color. However, the long tails of previous decades were replaced with the tuxedo, and most men wore a crisp white shirt underneath.

Overall, formality still ruled men’s fashion. Though more casual styles began appearing, the formality of previous decades carried over.

Lighter colors for formal suits denoted the wearer’s social status. Lighter colors, such as nudes and white, were favored by the wealthy. Wearing colors that could easily be stained suggested that the wearer’s bank account could handle ruining such fabric.

Pinstripes were also common. White collar workers frequently wore pinstripes as a sign of financial status.

The material and the fit set apart suit fashion from that time period. Before, suits were heavy, uncomfortable things from fabrics that were expensive and difficult to clean. Although suits now are far more comfortable than those of the 20s, the suits from that decade were a huge improvement in terms of material and fit.

Suits of the 20s were made of wool or a tweed blend. Though you might be dying thinking of wearing a wool suit now, this was a more comfortable material than what men had to choose from back then.

Suit jackets were single or double breasted. Suits made earlier in the decade favored a slim, fitted style, while suits from later in the period adopted the boxy style most commonly seen in gangster pictures.

If you look at suit lapels, even this small detail represented a departure from styles of previous eras. There were three or four buttons, and the lapels began above the buttons around the center of the chest. This type of high lapel was quite different than jacket styles before the 20s, in which lapels came further down around the abdomen area.

The lapel also featured a single button hole towards the top meant to hold a flower arrangement, known as a boutonnière.

Patterns were another popular feature of suits. If you remember the style of barbershop quartets, the checked and striped look is quite similar to what men were wearing then. Solid colors included browns and greens, and colors on the cool side, blues and grays.

Add a pocket square to make your suit more customized.

4. Coats

Cold weather dictated an overcoat. This type of coat reached well below the knee and was made of thick material such as wool. It was meant to be worn over the entire suit.

They featured several deep inner pockets, and the outer material was very heavy. There wasn’t much need for lining.

Another fashion trend at this time was the leather jacket. Leather jacket styles featured both fur collars and plain. They also had pockets and buttoned up the front. At times, a built-in belt wrapped around the waist. Unlike overcoats, they usually had a lining, typically fur.

A major trend of the time among ivy-league college students was wearing thick, full-length wearing raccoon fur coats. The fad was short lived, but it would later become a staple to Jazz Age era of fashion. In 1928, George Olsen recorded a song with lyrics covering the trend; it was titled, “Doin’ the Raccoon.”

The cost for a luxury raccoon jacket back then was around three to four-hundred dollars. In today’s times with inflation, the price would be around four-grand. Perhaps you can see why the trend of these fur coats was so popular. Their opulent price tag made them extremely desirable.

5. Vests

Part of the look of the 20s suit is achieved by wearing a vest. Vests aren’t as popular now, but they were essential to the overall twenties style. Vests streamlined the center of the body and highlighted the high lapel that was so in fashion.

Men would have a double breasted vest that came up high and fit snug. They would wear this with a single breasted jacket. This was a particularly common look among young men influenced by the styles of the modern art movement.

6. Pants

The twenties was a time of great variety for pant styles. Both straight and wide-legged pants were common, and for pants of a traditional length it was common to see “turn-ups.” This was seen in a wide bottom cuff, literally “turned up” from the bottom of the pant hem. The waist band came far higher than the wearer’s natural waist.

Another type of trouser commonly associated with the 20s were knickerbockers. These were baggy trousers worn in casual settings such as for golf or other sports. The knees were gathered, and they were typically worn with some kind of bright sock.

An offshoot of knickerbockers was a style called “plus-fours.” These were the same loose-fitting, gathered at the knee style, but they reached about 4 inches further down below the knee. Popular with golfers, they allowed for more freedom of movement when playing the sport. “Plus twos” were also available.

Overall, American style preferred baggier trouser styles, whether full length or the shortened knickerbockers. Men in the workplace had no need for casual golfing style, but they still preferred baggier full length trousers. These had plenty of material through the hip and thigh.

Many institutions banned plus fours and knickerbockers in an effort to reign in the casual styles of fashion. Although famous universities like Oxford required long pants, and knickerbockers didn’t survive to present times, the advent of more casual men’s fashion couldn’t be prevented.

Even the colors became brighter and more casual. Previously, solid or muted colors were most of the choices for men, but with the popularity of sports styles, patterns like stripes and checks as well as lighter colors became popular. This was attributed to the rise of the middle class, and the affluence of society in the post World War I age.

7. Shoes

One huge change that happened in the 20s was the emergence of color in shoes. Previous styles had been single color shoes, but in the 20s we see the wingtip style so associated with the jazz age.

They were a little more casual than previous decades’ single color spats, but they introduced flair into men’s footwear. Shoes could be two tone, with white and brown or black being the most popular colors.

Wingtips made an entrance. Although patent leather was still the only formal style shoe available, men began to wear this style with a perforated flap over the lace. This lent shoes an air of artsy design, and signaled that a man was part of the jazz age.

8. Driving Dress Style

With cars becoming more popular, and more affordable, it was only fitting that fashion would reflect a particular fascination with the automobile. Buying a car meant being part of modern times, and the fashion industry was quick to step in.

Clothing created specifically for driving included flat tweed caps, meant to hug the head close and stay on even when driving with an open top. They also wore driving gloves, hold overs from riding gloves, but vented for comfort.

This was also the perfect time for men to wear the new leather jackets made fashionable by Charles Lindbergh. They often included a white scarf as an accessory.

9. Athletic Influence

Previous to the 1920s, men’s fashion was impossibly formal, often requiring several changes per day as formal rules dictated.

The 20s saw some relaxation of formal dress rules for the upper and middle class. The influence of sports and the rise of sports stars caused some casual changes in the men’s fashion of the day.

Golf had a particular impact on men’s fashion. This style was influenced by the required uniforms of sports stars. This included sweaters in clean colors such as white or navy, and cable knits.

For casual pants, men paired these sweaters and knit shirts with the knickerbockers or plus-fours mentioned above.

A note on plus fours: The style popular among male golfers of the 1920s, allowed for easier movements on the course. They featured a four-inch lower drop below the knees in comparison to knickerbockers. Players wore them alongside argyle socks, which featured a classic diamond pattern. Gentlemen also paired the look with dress shirts, sweaters and silk neckties.

The casual and loosely fitting style came about after Edward, Prince of Wales made a diplomatic trip to America in 1924.

10. Hairstyles

Fashion wouldn’t be fashion if we didn’t mention hair. Clean, close shaven looks dominated the 20s, and hair was still widely influenced by military style.

Men usually wore their hair parted to the side with some kind of pomade to hold it in place. The pomades made the hair glossy, and the hair stayed slicked.

11. Accessories

Aside from hats, which were required in fashion, other accessories included suspenders in brighter colors, and around this time waist belts became more popular. As pants slimmed, men preferred these belts to hold them in place.

Other accessories were round framed glasses and sunglasses. Often worn while driving, men frequently paired them with straw hats for driving style.

For more formal wear, and for some of the upper class, bow ties were the ruling fashion. Men combined this style with pocket squares that lent a pop of color.

Men could also wear skinny knit ties in addition to the bow tie. This new style was more casual, and occasions that required semi-formal wear were perfect for this accessory.

12. Swimwear

Like women’s fashion, men’s swimwear fashion slimmed down to make swimming easier. It featured larger arm holes for ease of movement. They were mostly two pieces, a pair of shorts and a longer tank top that came down just above the end of the shorts.

Sleeves were removed to allow more freedom of movement, and as the decade progressed, it became more common to see slim, sleeveless swim costumes.

In the later 20s, the shirt was shortened, and was usually worn with belted shorts. This was shocking at first, but professional swimmers wore this style until it became more common for everyone.

13. Modernizing These Styles

The 20s remain the hallmark of modern men’s fashion. Many of the suit styles seen today still reflect the changes made during this time period. You don’t have to buy vintage clothing to take advantage of the style.

Keep in mind clean looks in all aspects, hair down to the shoes. Consider buying a well-made, and well fitting hat. Make sure that your shoes are well maintained, and that your suit has at least three pieces, jacket, vest, and trousers. You just can’t go wrong.

1920s men’s fashion still looks great today. You could use this style for formal occasions or for an eye-catching Halloween costume!