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If you’re into cosplay or you’ve got a costume party coming up, you’ll want to look the part. Anyone can throw on a suit and claim that they are Jay Gatsby, but that doesn’t really cut it, now does it?
Perhaps you’re tired of seeing the same old gangster pinstripe suits or formal dress dinner-type jackets, and you’d like to check out some of the casual wear.
We’ve got the answer for you! From sweaters to newspaper boys, we’re going to show you how you can pull off a nearly perfect imitation of Jay Gatsby or Jack from Titanic.
What Was Men’s Casual Wear in the 1920s?
While we are much more laid back in style 100 years after the Jazz Age, men did have casual clothing and wore casual pants, just not nearly the selection that we see today.
Jeans were fairly new and had yet to be seen in big cities. You could wear jeans, chaps, a plaid shirt, boots, and a hat and call yourself a 1920s cowboy, but most people would call that outfit into question, considering that cowboys haven’t changed their attire all that much over the years.
Younger men loved fashion, and for many of them, they liked to vary their look. College men, for example, were fond of sweaters. Whether it was a regular V-neck sweater or more of a vest sweater,
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one thing was certain, they loved patterns.
College men rarely wore a shirt under their sweaters unless they wear the sweater vest. You can pair any sweater with some tweed pants
and a straw hat, and you’re ready to graduate, college boy!
Oh yes, let’s not forget some snappy-looking wingtips for the up-and-coming businessman
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For cosplay or costume parties, however, you may want to look like a small-town gentleman or the big-city slicker.
The Small-Town Gentleman
Imagine yourself as the owner of a small-town grocery store, or perhaps you work for a local bank in town.
You want to look smart, but you don’t have a lot of cash to spend on expensive clothing.
The shopkeeper would wear a plain white shirt
with arm garters to hold up the sleeves on a hot summer day, and perhaps a bow tie to look more like a gentleman.
Chances are that you’ll wear an apron, especially if you’re handling anything messy
Men in construction or men who would do physical labor would probably wear something similar to the shopkeeper but no tie, and they would have a workman’s apron
Let’s not forget construction worker’s boots!
True laborers, such as mechanics or farmers, wore overalls.
These were meant to last for decades, so you can wear ones that are dirty or very faded. Match it with a long-sleeved plaid or checked shirt and boots for an easy to pull off the look!
Small-town bankers or businessmen would always wear a suit.
It’s strange to think of suits as being casual wear, but the truth is that nearly all men, other than those in blue-collar jobs, wore suits the majority of their lives!
You can dress up this three-piece suit to look like Nick Carraway in The Great Gatsby, simply by adding a straw hat, suspenders, and a gold watch chain.
Wealthy Big City Slickers
Wealthy men or men from the big city were always “on parade” so to speak. They knew that all eyes were on them, and they were proud of who they were. You would almost never catch a wealthy man in anything but a full three-piece suit, although they did love patterns and colors!
No well-dressed man would go out without his hat and the proper shoes.
Hat styles varied, but the most common for the wealthy or big-city businessmen were fedoras, newsboy caps,
and what was known as “boaters” or even Pork Pie hats.
Shoes were almost always what we call wingtips but were known back then as Oxfords.
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The favored colors were either brown or black 
and two-toned shoes were the ultimate in sophistication.
Most businessmen or wealthy men would wear plain wingtips during normal hours and save their two-toned shoes for formal occasions, such as parties or weddings.
What Other Casual Outfits Did Men Wear in the 1920s?
While women had lots of options when it came to fashion, men not so much. Regardless of the weather or the occasion, you would find men dressed in a three-piece suit unless they had blue-collar type working jobs.
Men’s Costumes and Attire in the Style of the 1920s from The Great Gatsby
One can picture a gentleman of the Jazz Age taking off his coat and vest and wearing only suspenders and a shirt when home alone. You can try that route if you mix the suspenders/shirt option with the right accessories.
If you picture a banker who had been drinking the night before and woke up in the morning to find guests in his home, that should give you a mental image of the casual alternative look you might want to pull off.
This would mean a white shirt, perhaps with the sleeve garters, a one or two-day beard stubble, suspenders, maybe a bow tie,
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and some very nice dress pants.
Add a cigar and some nice shoes, and you’ve got a banker on his day off.
Men’s fashion also involved a few other types of clothing, such as golf attire. You didn’t have to be an avid golfer or even do anything more than chip a few golf balls to be entitled to wear a golfing outfit.
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You might feel like turning up your nose at some of the outlandish golf outfits you’ll see, but back in the day, this ensemble in colorful patterns was the style.
Picture the 3-Stooges golfing, and you’ll have the perfect outfit!
During prohibition, many lower class men took to wearing what would be called newsboy outfits ( see more 1920s Mens Outfits here ). Yes, despite being men, they were still called newsboy. These were delivery men who disguised their “deliveries” as newspaper sales.
Everyone has heard of Good Time Charlie. You know him! The guy with no money who has one nice suit and tries to pass himself off as a gentleman. He takes your money during the good times and then quickly disappears.
You might have heard of this guy as the “Love ‘Em and Leave ‘Em Larry.” Same guy, same style!
If you’re attending a beach or pool party, you can really shake things up by wearing the typical 1920s swim suit. These were similar to long underwear but had shorter legs and short sleeves.
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Bootleggers were also well known, and while some became very wealthy and tried to pass themselves off as coming from “old money” (Think Jay Gatsby), this wasn’t that common.
More common was the working man selling bootleg liquor to local speakeasies. The old-fashioned pants with buttons for suspenders and a newsboy hat make this an easy but genuine outfit.
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During this time period, men were adventurers! They frequently longed to do something daring, and many took up riding motorcycles.
You can wear a leather jacket, leather pants,
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and the vintage leather hat that was the only thing available before helmets!
Oh yes, the right eyewear is a must!
Not everyone was a gangster or a bootlegger, despite what the movies may have led us to believe.
Young men felt similar to young women of the time and wanted to do something daring and be different from their parents.
Other Casual Sports Wear from the Jazz Age
Sometimes daring to be different from their parents wasn’t quite as “different” as they imagined, but the clothing certainly led them to believe they were trailblazers!
In addition to golf, tennis also became widely popular during this time. For most men, this was a sport for the rich and to own a tennis racket meant you were very well off, even if you didn’t play! I suppose you simply carried the racket around!
This is another easy outfit to create. Carry a tennis racket ( they were made of wood but you might be hard pressed to find one today). If you can’t find wood, a brown racket, like this one, might pass.
The outfit is super easy. Choose a light colored (white, yellow, or pink) suit without the vest or jacket.
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White shoes were also a must but not tennis shoes. They hadn’t been invented yet.
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During the 1920s, men did not wear shorts or tank tops for anything other than a few sports where ladies were not allowed.
Men who were weightlifters, boxers, or who played basketball could be found wearing shorts with tank tops that had a high neck and socks that not only went to the knee, but over the knee!
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It appears that seeing a man’s bare leg and arms were just too sexy for the average woman!
Other Miscellaneous Outfits of the Times
You’ve certainly heard of the Barbershop Quartet. Now these were frequently men who traveled around the state, so they often had matching outfits that they wore only while working.
Wear this vertical stripes suit with a pocket watch for a smart casual look.
Bartenders were also dressed a bit more casually, and often wore the vest, arm garters, a bow tie, and an apron that covered only the lower half of the body. I’m betting that when they left the bar, they ditched the apron for their suit jacket
Whether you owned a yacht or a sailboat, you wanted to dress the part! No swim shorts or tank tops for the sailing crowd! Even if it was a rowboat, a properly dressed man would wear usually a navy blue coat, especially if it had gold buttons, white pants, and white shoes.
The sailing outfit is mentioned in The Great Gatsby, where Nick sees a photo of Dan Cody and Jay both wearing “yachting costume.
This jacket can also be double breasted and possibly even a white hat with a black bill would be worn.
If it was a large boat and you were one of the sailors in charge, you were expected to also wear a navy blue uniform, often with a loose white tie.
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In the hottest summer months, it would also be common to see men (not for men at work or blue collar jobs, of course) wearing all-white suits.
The shirt might be a pale pastel color, such as robins egg blue or even pink, but white suits were thought to be cooler than most others.
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You’ll remember that on what was the hottest day of the year in The Great Gatsby, Jay Gatsby wore a pink suit, and Daisy told him that he “always looked so cool.”
I do wonder how some men dealt with the extreme heat and humidity of the summer months wearing those 3-piece suits and hats. I suppose they became accustomed to it, the way women somehow lived with corsets, bustles, and layers of petticoats and floor-length skirts.
Final Thoughts on 1920s Mens Casual Wear
Men were fairly rigid in their clothing choices in the 1920s. They wouldn’t get relief from those three-piece suits for another 25 years or so.
Even today, the best dressed men, business men, and any man looking to make an impression must wear a suit if they want to be taken seriously.
While men today do have far more casual clothing options, I must say that the style and formality that the suits from the 1920s really strike me as something special.
Personally, I’m tired of the sagging jeans and butt crack look, as well as the beanies that look as if they are never washed.
Casual wear is fine in its place, but I’m sure men from the Jazz Age would be just as horrified by what they see men wear today as I am.
Let’s bring back hats! Spats! Sports coats and bow ties!
Who agrees with me?
