Men’s 1920s Shoes History and Buying Guide

What style of shoes did men wear in the 1920s?

Just as ladies were losing the confined boots for everyday-wear in the 1920s, so were men. The boot was losing favor, and the more comfortable lace up Oxford shoe look its place.

Men’s 1920s dress shoes were not the only style to get a foothold in the ’20s. Tennis shoes, two tone shoes, and slippers also emerged as shoes worn by the ordinary man.

 1922 men’s boots and shoes- notice the pointed toes

Continue reading about the styles of 1920s men’s shoes such as the lace up boot, the oxford shoes, the wingtip shoe,  the two tone oxford casual shoe,  sneakers, work boots, winter boots, summer sandals, and house slippers.

Next shop for 1920s style shoes for your upcoming 1920s event.

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New 1920s style mens shoes and boots. Buy now.

1920s Men’s Boots

In the early 1920s, men still wore cap toe lace up boots. This style had been around for over 50 years already. Sturdy, comfortable, dressy enough for gentlemen, and durable enough for the working man, there was little choice to wear anything else. Colors were black, brown and grey.

The design on the toe featured a band across, with small brogue holes for decoration and breathability. Some fancier versions had patterns with decorative broguing on the toe top, too. Heels were thick with a short stacked heel.

Only traditional or conservative gentlemen chose to wear dress boots in the 1920s. Work boots remained, but they took on new styles specific to the industry (more on them later in the article).

Shoe spats were one item that continued into the 1920s as strongly as before with certain fashionable gentlemen. I am referring to Gangsters, Bootleggers and other notorious thugs of the 1920s.

With all that money from illegal alcohol sales making them filthy rich, they made an art of wearing the most high end fashions.

1928 Men’s Spats

Grey, tan or off-white wool or linen spats with pearl buttons on the sides became synonymous with gangsters. The movies portrayed men in these style and the general public copied them.

One trend was to wear spats along with a finely tailored vest, called the Boulevard style as in Hollywood Boulevard style. Next time you watch Boardwalk Empire take notice of the gangsters’ spats. Shop here for spats.

Rudolph Valentino wears white spats over his boots

1920s Oxford Shoes

Looking at 1920s men’s shoes, you could hardly tell if they were wearing boots or Oxfords. The only difference was the missing upper half. Hidden under trousers, this was difficult to see.

The cap toe Oxford shoe in black, dark brown or red-brown was the most common men’s shoe of the 1920s. Shoe companies tried to introduce lighter browns for summer-wear, but men were slow to adopt these new shades.

Black went with everything and stayed the cleanest – why be dirty in dusty brown?

1927 Black Cape Toe Boots and Shoes

What men appreciated in the 1920s was the more roomy toe. The sharp pointed toe of the teens and early ’20s was replaced by round toe or wide box toe Oxfords.

1920s oxford shoes were quite heavy and chunky looking, which balanced out the wide Oxford bags men were sporting during the mid twenties.

Later 20s years saw the toe relax back into a natural round shape again to go with longer, leaner trousers.

1920s men’s shoe soles had been leather for centuries. Now some shoes were sporting the new rubber heels and full soles.

While the early years were a bit plain, the later twenties saw more creative decoration using reptile skins like alligator, or embossed leather to look like alligator skin if a man couldn’t afford the real thing. Skin leather was heavy and the trend didn’t take too quickly.

1927 Men’s box toe shoes with embossed leather panels

1920s Wingtip Shoes

One decoration variation with Oxford shoes was the wingtip design. Instead of a line straight across the toe, the line now curved to form a “W.”

The W for wingtip came in a variety of lengths such as the semi, quarter, and long wingtip. In general, the wingtip Oxford was more formal and less common than the cap toe.

Broguing, foxing and top stitching details added to the fancy look of wingtip shoes.

1922 Wingtip and Cap Toe Shoes in Brown or White

1920s Two Tone Sport Shoes

When most men dress in 1920s style, they are quick to wear a pair of two-tone Oxfords. Rightly so, because after plain black or brown shoes came the love affair with brown and white wingtip Oxfords.

Two tone men’s 1920s shoes were casual and semi-formal at the same time. They mixed well with the sports tweeds, linen, and flannel suits, and looked especially fine as golf shoes worn with knickers.

1922 all white shirt for suits or weekend sports

The two-tone spectator Oxford became men’s “new” footwear of the decade. Black and white as well as the occasional grey and white Oxford were alternatives to the very popular brown and white.

Worn year round, men’ s1920s casual oxford shoes could be all leather, a mix of patent and matte leather, or canvas and leather.

Cap toes and wingtips were the trendiest patterns. Rubber heels and soles were a must for sportswear.

Saddle shoes

With a white band in the center and dark color on the heel and toe, saddle shoes were available in the 1920s, but they did not become very trendy until the late 1930s. They were only a sport shoe and were not worn with casual or business attire.

Leather “saddle” golf shoes

Golf shoes could be the saddle design or the fancier wingtip. Golf shoes also started to have rubber nubs on the soles, which were early versions of cleats on both men and women’s shoes.

Golfing in Two Tone Shoes (The tall guy apparently missed the memo)

Besides golf, men’s 1920s two tone oxford shoes were worn for sailing, tennis, bowling, cricket, and other trendy sports or for general “outing” wear.

1920s White Shoes

White shoes for women were only allowed in summer months. For men, that was generally true, too, but many fashionable gentlemen, especially in sunny California or Florida, wore white shoes year round.

Most 1920s men’s white oxfords were made from “mail bag” white canvas with a leather or rubber crepe sole.  They were worn with white suits and “outing clothes” and certain sports such as tennis or cricket.  They were difficult to keep clean which is while only the wealthy wore them.

1927 white canvas oxford summer shoes

The really stylin’ wealthy wore white nubuck shoes, called ‘bucks’ for short. Nubuck was the “wrong side” of leather sanded into a velvety finish. Soft, supple, and flexible, they were extremely comfortable shoes for summer or winter.

Other Nubuck colors existed, too. There was an industry push for light brown bucks that was met with resistance. In 1929, there was another push for “hotdog” bucks or kidskin shoes in red, green or blue. Again, they were slow to be adopted until the mid 1930s.

For all the advancement of men’s clothing and fashion in the 1920s, they were extremely stubborn about changing their shoes!

1929 linen white suit, canvas oxfords, with panama hat worn by Sen, Frank Kellogg

1920s Sneakers

In 1917,  “Chuck Taylor All Stars” Converse shoes were made as one of the original tennis shoes.  The All Star sport shoe design has changed very little since then.

In 1923, the Chuck Taylor signature was added to the patch, giving him well deserved recognition for taking the shoe to athletes of every sport, but especially basketball. They outfitted popular teams with shoes, teams that were known for their stylistic playing skills.

The flashy spins and quick moves on the court proved how light, smooth and flexible Converse shoes were.

1922 mens canvas sport shoes, boots, high and low top sneakers. Sandals top and center.

The public caught on and soon enough all athletes — men, women and children — were wearing “tennis shoes.”

The 1920s sneaker was a white high top, with black or brown rubber gum crepe soles and a round seal over the ankle. Dark leather and canvas versions were equally popular with high school and college-aged students.

They were worn for all types of indoor sports or outdoor activities, including hiking, baseball, track and field, and football and at the gym.

1925 Black and White Basketball Shoes

Sandals

Men’s sandals were not part of the footwear world until the late 1930s. The closest shoe was a “cool down oxford” with a few cutouts for ventilation on the toe box and side of the shoe.

There were also canvas shoes made specifically for swimming at the beach worn by both women and men.

1925 men’s ventilated sandal oxford

1920s Men’s Work Boots

For the hard working labor man, he lived almost entirely in his work boots.

In the early twenties, working mens boots looked very similar to gentlemen’s business boots, except they had a thicker sole, wider toe with rounded extra thick toe cap, and sometimes extra lining in wool or sheepskin for warmth. Hight’s could be ankle high for foot flexibility or up to over-the-calf for heavy duty occupations.

The leather had to be thick and tough — often double tanned for durability. It was around this time that Australia was importing Kangaroo leather as one of the most durable and weather resistant leathers. Australian work boots were imported, too, for those that could afford them.

Rubber boots were offered in various heights and waterproofness for jobs such as dairymen, farmers and hunters.

By the mid twenties, men’s shoes borrowed the Native American moccasin design for their work boots. The moccasin toe reduced the amount of laces showing below the pant cuff, thus reducing the opportunity for the laces to get caught on machinery.

The design was more flexible, too, without that heavy toe cap, making them ideal for mining, farming, and construction jobs.

Learn more about men’s 1920s workwear and work shoes. 

1927 Moccasin Toe Work Boots

1920s Men’s Winter Boots

In severe weather, 1920s men’s winter boots looked like work boots. Even gentlemen wore them through rain and snow.

Rubber shoes with leather legs worked great in the mud and rain seasons. Extra high legs, thick linings, and often coated in rubber, winter boots did their job in snow, too. More about men’s vintage winter boots and shoes. 

1920s Men’s House Slippers

When work was done for the day, those tough boots came off and feet slipped into a nice soft pair of house slippers. Ahhhhh, comfort at last!

Men’s house slippers came in so many styles: moccasin, opera, tuxedo or everett, romeo and carpet slippers. I could write an entire article on just the various style of men’s slippers.

1920 leather slippers- opera, romeo, everett with pipe motif, Hi-Lo, Everetts

In short, they were made of leather or felt, lined with soft flannel or silk for the upper most classes.

The “opera” slipper is the one style reintroduced by the recent The Great Gatsby movie, and is very popular with men today.

More about men’s vintage slippers, plus where to find similar pairs todays. 

1920s Style Men’s Shoes Today

Now that we have covered the history and fashion of men’s 1920s shoes, we can take a look at what is available to us today.

Thanks to the 1920s fashion revival, we have a return of many 1920s style boots and shoes. You can shop for them here.

What to look for in footwear.

• 1. Cap toe lace up boots or oxfords in brown or lack. The best brown is a “rust” color instead of dark brown.
• 2. White canvas or buck shoes in summer.
• 3. Two tone spectator oxfords.
• 4. Fancy wingtip oxfords too.
• 5. Lace up leather work boots
• 6. White Converse high top sneakers

Buy 1920s Style Men’s Shoes

Common 1920s and 1930s style men’s shoes: Two tone shoes, Wingtips, Cap toes, classic converse, white Nubucks, and lace up boots.