7 Easy 1920s Men’s Costumes Ideas

So you have a prohibition era 1920s event to dress up for and you don’t know what to wear? Here are 7 men’s 1920s costumes you can make from clothing you may already have or can attain from a thrift store, new clothing store or online retailer. How “easy” it will depend on what you can find and how much you want to spend. Unfortunately, there is not a single store that carries these looks as complete outfits, although Paul Fredrick comes close.  We collected these costumes over a few years of looking, so don’t be dismayed if you can’t find the “perfect” look the first time out.

For easy 1920s women’s costumes, look here. 

1920’s Men’s Costumes

1920s Working Class Men’s Costume

A casual or working class 1920’s men’s costume

One of the easiest 1920s looks is a working class or casual men’s style. Poor or working class men couldn’t afford fancy three piece suits, nor were they practical in labor intensive jobs. Men simply wore a pair of pants, suspenders, vest, shirt, shoes, and hat. Colors were a bit drab in brown, grey, and navy blue. Texture was a big thing in the 20s, so most materials was a rough wool or thick tweed. The fabric had a defined pattern, too, such as plaid, stripes, and herringbone.

Shop vintage style men’s suspender/ braces

When shopping for 1920s pants, you want to find flat front, high-waisted pants (no modern skinny or low waist trousers). The early ’20s had a classic width leg, while the mid and late ’20s had a very wide leg. Wide legs will be harder to find with flat fronts. To get a higher waist get, pants one or two sizes up and use your suspenders to hold them up. For that extra ’20s touch, cuff your pants legs  2-3 inches (not shown here.)

Next add a coordinating vest. It doesn’t have to match, but it should be in the same color family. 1920s vests had lapels and usually buttoned up high on the chest. Shop for 1920s style vests here. 

The shirt can be white or a striped, colored dress shirt with or without a collar. Any dress shirt you already have will work fine. Roll up the sleeves for that working class touch. A collarless or mandarin collar shirt will make you look like you couldn’t afford a detachable white collar and is also very period appropriate. If you want to wear a necktie go ahead. Working class ties were thin strips of fabric or hand knit ties. Both are popular styles right now, so they will be easy to shop for.

Your shoes should be basic, plain, lace up Oxfords in brown or black. Lace up boots would be OK too. A cap toe was the most common detail on shoes at the time. A working class man couldn’t afford fancier wingtips or two tone shoes. Buy 1920s style men’s shoes here.  Learn about 1920s men’s  shoe history here. 

The 1920s style cap is a must for your costume. The style at the time is what’s called an 8 panel cap or newsboy cap today. It’s not sleek and form-fitting like the ’30s styles, instead it is wide and floppy.  Common fabrics were tweed, textured wool, felt, leather, and corduroy for winter, linen or cotton in summer. Buy 1920s style hats and caps here. 

Men’s Vintage Workwear– 1900-1940s- striped overalls, wool flannel shirt, denim jacket, cap, gloves and sturdy work boots.

More vintage men’s workwear clothing history. 

1920s Business Class Men’s Costume

Business Class Brown Suit

A step above the working class man is the business class man.  He is nicely dressed with an affordable suit that may be a few years old but not out of date.

Art Deco Era Men’s Look- Fedora hat, plaid suit, two tone shoes.

Suit: A matching 2 or 3 piece suit is ideal, but if you can’t get one, then choose at least pants and a jacket that are the same color. In this picture, the pants are flat fronts from the ’70s, and the jacket is a brown and white striped wool. Underneath is the same brown vest from the above costume. Ideally, a 1920s suit should button up higher but the striped jacket is an ideal ’20s pattern. New 1920s style suits here. 

Shirt: The shirt is a subtle striped dress shirt with a detachable white club (round) collar. A white shirt or solid pastel shirt would be fine, too, but stripes were the “in” thing to wear. An attached white collar shirt will be easier to find. A colored collar shirt is also OK for a late ’20s look. Learn about men’s shirts and where to buy detachable collars. Buy 1920s style shirts here. 

Tie: A necktie in paisley, small pattern or horizontal wide stripes are the semi formal tie option. A bow tie is also another fun and period-correct alternative. Wear a polka dot tie for something unique and very ’20s.   Learn about and shop for men’s ties. 

1920s Men’s Hat Styles

Hat: Several kinds of hats can be worn by business class men. The Bowler or Derby (pictured) was a carry over from the previous decades. It’s most noteworthy fan was Charley Chaplin. Men also wore high crown fedoras, rolled edge Homburgs and straw hats like the Boater, Skimmer or Panama in the summer. Learn about men’s hat styles here. 

Shoes: A brown suits needs brown lace up Oxfords or boots. A grey or navy suit needs black oxfords. Cap toes or wingtips were a good men’s shoe. Learn about 1920s men’s shoe history. 

Shop men’s 1920s style shoes:

1920s Men’s Upper Class Suit / Gangster/ Bootlegger Suit

Upper Class Men’s Costume

For a well-to-do man, like the Great Gatsby or Al Capone and his band of bootleggers, a complete head to toe look is important. They were the fashion leaders of the day.

Suit: Striped or plaid suits in brighter colors started to appear around 1923-4. They can be a challenge to find today but are well worth it when you find one. We found ours at Dillard’s in the early summer made by Perry Ellis. It is a linen blue with white shadow stripes (wider than pinstripes). Stripes and plaid should be noticeable, not subtle. Single- or double-breasted styles are both common. Pants should be flat front, not pleated, and cuffed at the ankle. Buy new 1920s style suits here. 

Shirt and tie: Same as above costume. This time add a coordinating pocket square to the jacket (oops, we forgot to do this!). Another thing we could have added was a collar bar. Learn about shirts and collar bars here. 

Hat: Same as above. For this summer look we put on a straw boater hat, which was very popular for spring and summer. A straw Panama hat is another wealthy man’s summer hat. For a casual look, a white 8 panel cap would also look well.

1920s Men’s Shoe Styles

Shoes: Now you can bring out your two tone shoes. Wingtips, saddle shoes, or cap toes with brown and cream patterns. Black and white is less common. Otherwise, a solid pair of black or brown wingtips will look dapper when worn with a pair of white spats, too.

Accessories: Gloves in a color to compliment, but not necessarily match, the suit is an appropriate addition. A pocket watch on a chain is another, although you won’t see it unless you take your jacket off. A walking cane is an upper class accessory that will set you apart from the business class men. Buy 1920s mens accessories here. 

1920s Gangster look – Black homburg hat, dark grey striped suit, two tone shoes, leather gloves and a walking cane (or is it a weapon?)

More 1920s style men’s suits

1920s Men’s White Summer Suits

White Summer Suit

In the summer, for upper class men, white was the color to be seen in. White or ivory was worn at garden parties, summer house parties and at outdoor sporting events.

Suit: A white or ivory linen suit is nice and cool in summer. We found this white dinner jacket less prone to wrinkling than pure linen. A white dress shirt and summery gold tie complete this easy look on the left.

Pink! Bright pastel colors were trendy in the ’20s.

On the right we used a pink shirt and an “Art Deco” print grey tie. Pink was a bold new color that many trendy men were wearing (including the Great Gatsby).

Hat: Again, straw hats are a must in spring and summer. Here we used our straw boater again. Good Panamas are quite expensive. We have gone through a few cheap ones fast. Don’t skimp if you can afford it.

Shoes: White suits need white shoes. In the latest Great Gatsby movie, Gatsby wore grey and white two-tone shoes with his look. While I have never seen this option elsewhere, I believe it is period correct.

1920s Golf Costume

The Sporty Look with Cable Knit Sweater

Golf, tennis, hiking, hunting…. any kind of sport in the 1920s had its own fashion. In the 1920s, most sports and casual sporty outfits embraced cropped pants called plus fours. They are similar to knickers, except you don’t see the cuff band around the knee because the pant leg bags over it 4 inches (or more). While you can buy new golf knickers, it’s easy enough to make a pair. The simplest technique is to buy a  pair of wide leg pants and either pin or sew in elastic to the cuff, then pull it up to your knee. For good sewers try this or this video tutorial. 

Sporty Costume with Pullover Vest

Next, add a pair of tall argyle socks (or any geometric pattern) and some two tone Oxfords. Bring back your newsboy cap from the working class look and you are now in the upper class golf league. This look also works for newsboys, teens and other casual men’s occupations or hobbies.

For your top, you can wear a chunky cable knit sweater (pictured left/above) or a button up dress shirt and pullover vest with shirt and tie (pictured right). Vests were either solid colors or crazy patterns, like argyle and fair isle. The sporting look is one style that loved to combine mismatched patterns, colors and textures. Have fun, be wild and crazy and you will look the ’20s part.

A look made popular by tennis stars was to wear white pants, shirt and pullover vest or sweater. Don’t forget to carry a vintage wood tennis racket to complete the look.

Casual 1920s look can be worn with or without a pullover vest.

Alissa and Ed sporting casual ’20s costumes

Men’s 1920s style vests and pullovers:

1920s Seersucker Suit

Blue and White Striped Seersucker Suit Costume

The seersucker striped suit goes back to the early 20th century but remained popular into the 1920s. The lightweight cotton seersucker material was perfect for summer suits. The small blue and white, grey and white, and even pink and white stripes fit right into the colorful patterns of most 1920s menswear.

For our seersucker costume, we choose a double-breasted suit with matching vest from Paul Fredrick. A single-breasted suit would have also been perfect for this ’20s look. We added a pink shirt with white collar (a great combination!) and blue bow tie, two tone shoes, straw boater hat, white gloves, and a walking cane.  Snazzy!

A common alternative to a full striped suit is to wear a striped jacket/blazer over white pants. It was a signature yachting uniform and popular costume for barbershop quartets.

Seersucker suit on the left; Ivory linen suit on the right. Both are perfect for hot summer events, from PaulFredrick.com

1920s Men’s Formal Suit

1920s white tie formal suit

For an after 6pm dinner party, evening at the opera or grooms wedding, dressing in men’s white tie suits was a requirement. Black tie was a semi formal look acceptable for immediate family dinners, and upper middle-class men. White tie means the vest and bow tie are also white. Black or white tie was also worn by waiters, bartenders, and nightclub party goers at upscale establishments.

This picture was taken for our 1890s themed wedding. Men’s white tie formal wear remained unchanged through the early ’20s. The mid ’20s saw more men wearing the casual dinner jacket, called a tuxedo today. The variations between tuxedo’s back then and now are minimal. If you have a tuxedo in your closet, by all means, wear it or rent one locally. Learn the history of men’s formalwear here and how to pull off the 1920s look using modern tuxedos here:

That’s it! 7 “easy” 1920s costumes for men.

Did I leave out a style you want to wear? Let me know in the comments and I will put one together.