1920s Men’s Casual Fashion: Get the Gatsby Look

Last Updated: March 21st, 2024 by Kerry Wisby (Teacher-BA English Literature, 1920s & Great Gatsby Expert)

This article contains links where we may earn a small commission at no cost to you: Learn more here

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?

a man wearing a 1920s Men's Gatsby Vintage Vest Set

Get this 1920s Look!

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.

a man in Sexy Cowboy Costume

Get this Sexy Cowboy Costume!

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.

Beretta Somerset V-Neck Lambswool Regular Fit Warm Casual Sweater, Gray Melange, Large

Get this 1920s Casual Wear!

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,

Kallspin Men's Cashmere Wool Blended Vest Sweater Relaxed Fit V Neck Sleeveless Knitted Vest Pullover (Navy Blue, 2X-Large)

Get this Knitted Men’s Sweater!

 one thing was certain, they loved patterns.

SPIEZ Mens Polo Shirts Collar Stripe Knitted Sweater for Men Stylish Button Down Cardigan Sweater Vintage Long Sleeve Bowling Shirt Comfortable Fit Navy X-Large

Get this Men’s Cardigan!

College men rarely wore a shirt under their sweaters unless they wear the sweater vest. You can pair any sweater with some tweed pants

Mens Vintage Tweed Dress Pants Herringbone Pattern Trousers Regular Fit Business Suit Pants(Brown,42W32L)

Get this Vintage Trouser!

 and a straw hat, and you’re ready to graduate, college boy!

1920s Mens Gatsby Straw Hat Set

Get this 1920 Men’s Hat!

Oh yes, let’s not forget some snappy-looking wingtips for the up-and-coming businessman

Bruno HOMME MODA ITALY PRINCE Men's Classic Modern Oxford Wingtip Lace Dress Shoes,PRINCE-3-BLACK,10.5 D(M) US

Get this Classic Shoes for Men!

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 shirtWhite Solid Long Sleeves Men's Suit Shirt

Get this Classic Longsleeves!

with arm garters to hold up the sleeves on a hot summer day, and perhaps a bow tie to look more like a gentleman.

1920s Mens Gatsby Vintage Vest Set

Get this 1920s Men’s Vest!

Chances are that you’ll wear an apron, especially if you’re handling anything messy

Buonelle Premium Chef Apron for Men – Adjustable Canvas Apron for Professional Chef - Kitchen Apron for Cooking with Pockets - Black

Get this Professional Apron!

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 apronQeeLink Leather Welding Work Shop Apron with 6 Tool Pockets, Heat & Flame Resistant Cowhide Heavy Duty Blacksmith Apron, 24" x 36

Get this Workman’s Apron!

Let’s not forget construction worker’s boots!

KEEN Utility Men's Cincinnati 6” Composite Toe Waterproof Wedge Work Boots, Belgian/Sandshell, 10.5 Medium US

Get the Boots!

True laborers, such as mechanics or farmers, wore overalls.

Walls mens Big Smith Stonewashed Bib overalls and coveralls workwear apparel, Stone Washed, 50W x 30L US

Get the 1920 Men’s 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!Mens Plaid Poplin Shirts Turn-up Collar Button Down Shirts Regular-fit Long Sleeve Tops Blue

Get this Checkered Shirt!

Small-town bankers or businessmen would always wear a suit.Black 3-Pieces Wedding Suits Tuxedo

Get this Vintage 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.

1920s Mens Gatsby Straw Hat Set

Get these Gatsby Accessories!

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!Grey Stripe Notched Lapel Men's 3 Pieces Suits

Get this 1920’s Suit!

No well-dressed man would go out without his hat and the proper shoes.

1920s Mens Panama Fedora Hat

Get the Gatsby Hat!

Hat styles varied, but the most common for the wealthy or big-city businessmen were fedoras, newsboy caps,

1920s Mens Gatsby Flapper Flat Cap

Get this Vintage Hat!

and what was known as “boaters” or even Pork Pie hats.

Wide Brim Boater Pork Pie Hat

Get this 20’s Hat!

Shoes were almost always what we call wingtips but were known back then as Oxfords.

Brown Monk Strap Men's Leather Slip-On Dress Shoes

Get the Classic Shoes for Men!

The favored colors were either brown or black Bruno Marc Men's Black Classic Brogue Wing Tip Lace Up Soft Round Toe Oxfords Formal Dress Shoes Size 12 M US Louis_1

Get the Formal Shoes!

and two-toned shoes were the ultimate in sophistication.

Ferro Aldo Arthur MFA139001D Mens Wingtip Two Tone Oxford Black and White Spectator Dress Shoes

Get the Retro Shoes!

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,

1920s Mens Panama Hat Flapper Set

Get the Gangster Accessory Set!

and some very nice dress pants.

Lars Amadeus Men's Green White Striped Dress Pants Straight Fit Color Block Office Work Suit Trousers 36

Get the Vintage Trouser!

Add a cigar and some nice shoes, and you’ve got a banker on his day off.

Black Slip-On Fringe Men's Party Shoes

Get the Fringe Shoes for Men!

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.

Men's Gone Golfing Costume

Get this 1920 Costume for Men!

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.

Rasta Imposta Mens Old Tyme Golfer, Green, Larger


Get this Retro Golf Outfit!

Picture the 3-Stooges golfing, and you’ll have the perfect outfit!

Golf Knickers Mens Albatross Golf Outfit - Pink - Golf Cap, 3 Argyle Socks - Size 36

Get this Golf 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.
Plus Size 20s Newsie Costume

Get this Vintage Look!

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.
Men's Good Time Charlie 1920s Mens Costume

Get this 1920 Costume!

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.

Fun Shack 1920s Mens Bathing Suit Costume 20s Swimsuit Halloween Costumes for Men - X-Large

Get the 20’s Halloween Outfit!

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.

Forum Novelties Men's Roaring 20s Boot Legger Costume, As Shown, Standard

Get the Men’s Roaring Costume!

During this time period, men were adventurers! They frequently longed to do something daring, and many took up riding motorcycles.

Mens Genuine Leather Biker Jacket Black | Vintage Brown Distressed Lambskin Motorcycle Jackets for Men (as1, alpha, xx_s, regular, regular)

Get the Leather Jacket!

You can wear a leather jacket, leather pants,

Homisy Leather Pants for Men Motorcycle Pant for Bikers Rider Moto Sports Street Cargo Trouser Real Pu Leather Black X-Large

Get the Classic Leather Trouser!

and the vintage leather hat that was the only thing available before helmets!

Aviator Helmet Black Leather Vintage Cap WWII Hat 2XL

Get the Vintage Leather Hat!

Oh yes, the right eyewear is a must!

ililily Aviator Hat Winter Snowboard Fur Ear Flaps Trooper Trapper Pilot Goggles, Light Brown

Get the Vintage Aviator Hat!

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.

LEI JARVIS Adult Carbon Fiber Tennis Racket, Recreational Tennis Racket, 27 Inch, Ultra Light Racket for Beginners and Professional Athletes, Racket Training for Men and Women

Get the Retro Tennis Racket!

The outfit is super easy. Choose a light colored (white, yellow, or pink) suit without the vest or jacket.

Goodthreads Men's Slim-Fit Washed Comfort Stretch Chino Pant, White, 28W x 29L

Get the Classic Pants for Men!

White shoes were also a must but not tennis shoes. They hadn’t been invented yet.

STACY ADAMS mens Summit Wingtip Lace-up Oxford, White, 7 US

Get the 20’s Style Men’s Shoes!

During the 1920s, men did not wear shorts or tank tops for anything other than a few sports where ladies were not allowed.

Dockers Men's Classic-Fit Perfect-Short - 34W - Sea Cliff (Cotton)

Get the Men’s Classic Shorts!

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!

Amazon Essentials Men's Regular-Fit Tank Top, Black/Charcoal Heather, X-Large

Get the Traditional Tank Top For Men!

It appears that seeing a man’s bare leg and arms were just too sexy for the average woman!

TCK Defender Over the Knee Football Socks (Navy, X-Large)

Get the Retro Knee Socks!

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.

Smiffys 50725XL 20s Barber Shop Costume, Men, Red & Cream, XL-Size 46"-48

Get this 1920 Outfit For Men!

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

Plus Size Old West Bartender Costume 2X

Get this Vintage Costume!

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.

Lands' End School Uniform Men's Long Hopsack Blazer 40 Deep Navy

Get this Classic Coat!

The sailing outfit is mentioned in The Great Gatsby, where Nick sees a photo of Dan Cody and Jay both wearing “yachting costume.

COOFANDY Mens Double Breasted Blazer Steampunk Vintage Jacket Victorian Frock Coat Cosplay Uniform Navy Blue Large

Get this Gatsby Jacket!

This jacket can also be double breasted and possibly even a white hat with a black bill would be worn.

Wall2Wall Captain's Yacht Sailors Hat Snapback Adjustable Sea Cap NAVY Costume Accessory (1 Pc)

Get the 1920 Sailor’s Hat!

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.

Forum Novelties Men's Ahoy Matey Sailor Costume, Blue/White, Standard

Get the Classic Sailor Outfit!

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.

White Peak Lapel Single Breasted 3 Piece Men's Wedding Suits

Get the 1920 Look!

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.

Long Sleeves Light Blue Solid Suit Shirt

Get the Men’s Vintage Suit Shirt!

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?


1920s Mens Casual Fashion Casual: Get the Gatsby Look
1920s Mens Casual Fashion Casual: Get the Gatsby Look
If you’ve watched The Great Gatsby or Peaky Blinders, you might be confused as to what men wore during the 1920s. Find out what casual attire men really wore in this era!
Gatsby Flapper Girl