Men In The Roaring 20s – So, you have a Prohibition Era 1920s event to dress up for and you don’t know what to wear? Here are 10+ men’s 1920s suits and outfits that you can make from clothes you already have or can get from a thrift store, new clothing store, or online retailer. How “easy” it is depends on what you find and how much you want to spend. Accuracy will also cost more than using current trendy fashions.
Unfortunately, there isn’t a single store that carries these 1920s men’s suits as complete outfits—instead, you may have to assemble the outfit from several retailers. We collected these costumes over several years, so don’t be disappointed if you don’t get the “perfect” look the first time. If you need help with your 1920s outfit, just ask us!
Men In The Roaring 20s
A casual or working-class 1920s men’s costume with thrift store clothes: flat front wool trousers, wool lapel waistcoat, collarless green shirt, newsboy cap and brown oxford shoes.
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One of the simplest 1920s looks is a working class or casual men’s style. Poor or working-class men could not afford fancy three-piece suits, nor were they practical in labor-intensive jobs. These men simply have pants, suspenders, vests, shirts, shoes, and hats. The colors were a bit dark and brown, gray and navy blue. Texture was a big thing in the 20s, so most materials were a rough wool or thick tweed. The fabric also had a defined pattern, such as plaid, stripes, and herringbone.
When shopping for 1920s trousers and pants, you want to find flat-front, high-waisted trousers (skinny fit and low-waisted trousers are not correct, but you can use them for a 20s-inspired outfit). The early 20s had a classic wide 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, buy pants one or two sizes up and use your suspenders to hold them up (button suspenders are best). For that extra ’20s touch, cuff your pant legs 2-3 inches (not shown here). Common colors were blue, brown and gray. In a pinch, you can also wear dark denim blue jeans as a workwear look.
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 were usually buttoned high on the chest. Shop for 1920s style vests here.
The shirt can be solid blue, grey, white or a striped, colored dress shirt with or without a collar. Any dress shirt you already have will work well or a flannel shirt with two pockets. Roll up your 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. A Henley white shirt peeking out from under your overskirt will look like vintage undershirts. Shop shirts.
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If you want to wear a tie, go ahead. Working class ties were thin strips of cloth or hand-knitted ties. Both are popular styles right now, so they’re easy to shop for.
Your shoes should be basic, plain, pointed oxfords in brown or black. Lace-up boots would be great too. A cap toe was the common detail on shoes at that time. A working-class man could not 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 that time is what is today called an 8-panel cap or newsboy cap. It’s not sleek and form-fitting like the 30s styles—instead, it’s wide and floppy. Common fabrics were tweed, textured wool, felt, leather and corduroy for winter, linen or cotton in summer. A beatup fedora is also workwear/casual fashion. Shop 1920s style hats and caps here.
Middle class business suit with brown pants striped brown suit jacket with a brown waistcoat, white club collar green dress shirt, brown bowler hat, paisley tie, and brown cap toe shoes.
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A step above the working class man is the business class man. He is nicely dressed in an affordable suit that is a few years old but not out of date. Early 20s suits were part of the skinny “jazz look” of neutral, plain colors, while mid to late 20s suits featured wide leg pants, wide lapels, and a wider range of colors and different patterns.
Suit: A matching 2 or 3 piece suit is ideal, but if you can’t, then at least choose trousers and a jacket that are the same color (all brown, all grey, all blue etc). Both single and double breasted suits were popular. In this picture, the pants are flat fronts from the 70s, and the jacket is a brown and white striped wool. Below is the same brown vest from the above suit. Ideally a 1920s suit should be a 3 or 4 button suit jacket, but the striped pattern is an ideal 20s pattern so the two button will do. Check out new 1920s style costumes here.
1920s Men’s Suit, Hat, Shirt, Tie and Shoe Combinations – Mixing suit, shirt and hat colors was more fashionable than an all matching set.
Shirt: The shirt we used is a subtly striped dress shirt with a detachable white club (round) collar. A solid pastel shirt would also be acceptable, but thin vertical stripes were the “in” thing to wear. A fitted white pointed collar shirt will be easier to find. A solid color collared shirt is also OK for the late 20s look. White dress shirts were unusual in the 1920s – color was in! Learn about men’s shirts and where to buy detachable collars. Shop 1920s style shirts here.
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Tie: A tie in paisley, small patterns or horizontal wide stripes is 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.
Hat: Different types of hats can be worn by business class men. The bowler or derby (pictured) was a carryover from the previous decade. Charlie Chaplin was a notable fan. Men also wear high crown fedoras, rolled brim homburgs and straw hats such as the boater, skimmer or Panama in summer. Young men sometimes paired caps with their suits instead of felt hats. Learn about men’s hat styles here.
Shoes: A brown suit needs brown pointed oxford shoes or boots. A gray or navy suit needs black oxfords. Cap toes or wings are a good and versatile men’s shoe. Two-tone brown and white shoes were very trendy for any color of suit. Black and white two-tone shoes weren’t quite in style yet, but will be easier to find today. Learn about 1920s men’s shoe history.
For the good man, like the Great Gatsby, Al Capone or the Peaky Blinders and his band of bootleggers, a complete head to toe look is important. They were the fashion leaders of the day. The black striped suit or “zoot suit” associated with the gangster look invented by Hollywood. In reality, wealthy men wore striped suits, but they were never black and “zoot suits” did not appear until the 1940s.
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Suit: Striped or plaid suits in lighter colors began around 1923-4. They can be a challenge to find today, but they will be worth it when you find one. We found ourselves made by Perry Ellis. It is a linen blue with white shadow stripes (wider than pinstripes). 1920s stripes and plaid should be noticeable, not subtle. Single- or double-breasted styles are both common. Pants should be flat in the front, not pleated, and cuffed at the ankles. Shop new 1920s style suits here.
Upper class men’s suit or gangster outfit with a striped blue suit, wing shoes, boater hat, gloves, white collar shirt and tie.
Shirt and tie: Same as above suit- striped or pastel shirts with white collar. This time we added a coordinating pocket square to the jacket (we forgot to do this!) Another thing we would have added was a collar.
Hat: For this summer look, we put together a straw boater hat, which was very popular for spring and summer. A Straw Panama Hat is another rich man’s summer hat. For a casual look, a white 8 panel cap will also look good. For fall/winter, rich men wear dark colored fedora or Homburg hats. Not black – dark blue, green, brown and gray felt hats are period correct and look very vintage.
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Shoes: Now you can bring out your two-tone shoes. Wingtips, saddle shoes or cap teeth with brown and cream patterns all work well. Black and white was less common. Otherwise, a solid pair of black or brown wings will look dapper when worn with a pair of white shoelaces.
Accessories: Gloves in a color to complement, but not necessarily match, the suit is a suitable addition. A pocket watch on one
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