Get the Great Gatsby Look with This Guide to 1920’s Men’s Fashion

It’s hard to believe that a century has already passed, but here we are. The roaring ’20s are here again (though maybe it’s just me, they don’t feel quite as roarin’ this time around.) On the heels of Leonardo Dicaprio’s 2013 rendition of the Great Gatsby, popular TV shows like Peaky Blinders and Boardwalk Empire, a 1920’s fashion renaissance, has been steadily gaining a foothold. It’s no wonder, as the population at the time was among the most sharply dressed of all time. The ’20s saw the birth of modern menswear and playfulness of style that continues to be iterated and riffed upon to this day. But what exactly made this time so unique?

It was a perfect storm of historical factors. WWI had just ended, reshuffling the deck of world players, with the United States ending up in a prosperous and advantageous position near the top due to its role in the war. Life was good for the first time in a while, and the post-conflict economy was booming like never before. Revolutionary social changes were happening; women were liberated and able to vote for the first time, which caused a reassessment of many rigid structures that had been maintained simply because they always had been. Hollywood cinema cast idealistic and richly textured images onto the collective subconscious, birthing movie stars and the desire to emulate them. The phenomenon of Jazz music and dance swept over the nation’s speakeasies and music venues, bringing a colourful style of its own and a youthful exuberance along with it. Everything was shiny, brand new, and exciting.

In this 1920’s men’s fashion guide, we’ll give you some background on where these fashionable styles came from and advice on how you can Jazz up your ensemble to turn heads like an early film star, or better yet, a slick and sophisticated gangster.

1920’s Style Categories

The Great War did much to level disparities between working and so-called upper-class citizens, as the rigours of battle were indiscriminate. That being said, the tiered strata of society still existed, and with them came different types of apparel, though virtually all men of the era projected a refined appearance as best they could.

Worker’s Wear

Wartime infrastructure enabled manufacturers to mass-produce quality threads efficiently and cost-effectively. Supercharged production made dapper clothing more affordable to the common man than had ever been the case before. The average worker could finally manage to express themselves through fashion choices without impacting their more basic needs. Even low-paid workers usually owned at least one suit.

Men's Workwear 1920s
Men's Workwear 1920s

A working man’s on-the-job apparel was often durable, utilitarian, comfortably loose-fitting, and replete with pockets for storing tools of their given trade. Farmhands and other labourers wore denim overalls, while those that worked closely with machinery, like mechanics or aviators, opted for unadorned coveralls (sort of like a jumpsuit that went over your clothes). The coveralls prevented straps and loose sleeves from getting tangled in the equipment.

The lines between the traditional classes were further obscured by wealthy men realizing how comfortable casual clothing could be, opting for a dressed-down look in their leisure time.

Business Wear

Business settings also became less rigid. As the name would suggest, the lounge suit was once considered too casual for a serious office environment. These attitudes relaxed in the post-war age of prosperity and comfort, allowing the lounge suit to evolve into what we now recognize as the modern business suit.

Such suits came in two or three pieces, were often double-breasted, and became the everyday uniform of white-collar workers and management. This continues today, with most Western world leaders, politicians, and business professionals wearing variations on the style.

Formal Wear

At the start of the decade, formal attire remained very traditional, similar to the tailored Edwardian styles that predominated before. Think Bugs Bunny playing his piano concerto. 1920’s men’s evening fashion was dictated by “White tie” events, like weddings or state dinners, which called for the traditional long-tailed tuxedo jacket, cummerbund, black silk or satin tophat, patent leather shoes shined to a showbiz sparkle, and a range of indispensable accessories. These items included delicately chained pocket watches, gold-tipped canes, white parade gloves, fancy white shoe-covers called spats, triangular silk pocket squares, and white flower boutonnieres, all punctuated by the eponymous white bowtie.

Less formal “black tie” events usually called for a shorter black tuxedo coat with peak lapels, a single-button closure, matching waistcoat, and straight-cut tuxedo pants. Such outfits were suitable for an outing to the theatre, small dinner parties, entertaining guests at home, or dining out at a restaurant.


Hat guys, myself included, lament a bygone era in which hats were worn almost universally. If you look at a picture of any sizeable crowd from the 1920s, almost everyone had a hat on. At the time, it was a sign of respect and an indicator of social class. No ensemble was complete without one.

Hats of the 1920s were made of materials like felt, wool, velour, or corduroy. Wealthier individuals sported top hats, homburgs, or the ever-versatile fedora, which featured a wider brim than is typical in today’s version. A similar hat, the trilby (popularized in a later decade by Frank Sinatra), featured a narrower brim and a shorter crown that was slightly angled forward. During summer, a light blazer paired nicely with a straw boater, a shallow stiff-brimmed hat; a boater was called a skimmer if the brim was wide. These durable, breathable straw hats could be rolled up and stored in a pocket as well.

1920s Men's Fashion Hats
1920s Men's Fashion Hats

Working-class and poorer citizens usually opted for a wool newsboy or flat cap. These wide and floppy caps also adorned the crowns of rich men of leisure while they drove cars or putted around the golf course. Black or brown felt bowlers (called derby hats in the states) were also a common sight.


Snazzy suits, as we’d recognize them today, really came into their own during this period, though they evolved dramatically over the decade. At first, suits retained a slim ‘Edwardian’ silhouette, but as men returned from war with bulkier, more muscular frames, suits became wider and looser-fitting to accommodate. A typical men’s suit of the early ’20s had a two-button closure, was single-breasted with softly rolled lapels, functional pockets, and alpaca lining. Wool, tweed, and corduroy were the predominant materials, featuring bold patterns on a muted colour palette. Patterns like vertical pinstripes, plaid, subtle checks, and herringbone were popular.

1920s Men's Fashion Suits

Suits that came later were broad-shouldered, with a shorter double-breasted jacket, 3 or 4 button closure, and wider lapels. As time went on, suit trends moved away from long swallow-tailed jackets that appeared outdated and stiff toward a modern cut that accentuated the athletic man’s physique. Accompanying suit trousers underwent a similar transition, from a narrow straight profile short enough to show some socks to an almost baggy, leisurely style.

Ties featured ornate art-deco-inspired patterns, along with the classic checks, plaids, and stripes.

The most common suit colours were grey, brown, and blue (when emulating the style, avoid the now ubiquitous black, which was only reserved for mourning and funerals.) Lighter-coloured suits of beige or cream indicated wealth and status. In summer, a striped seersucker or ivory-white linen suit would keep you looking good without sweating under heavy wool. A navy or striped blazer with white trousers was a more casual summer look, popularized by barbershop singers and young college students.


Due to the high-waisted pants, along with high-buttoning suit jackets and vests, only the uppermost portion and cuffs of a shirt would show. Designers leaned into making these parts of the shirt unique for maximum eye-catching impact. During the early ’20s, most collars were detachable ones affixed by buttons to the shirt body; by the middle of the decade, attached collars became more common, as they were a bit softer and more comfortable. Often the collar and cuffs would be white, with a patterned or vividly-coloured shirt body for contrast. While suit colours were usually subdued, stylish men didn’t shy away from a vibrant shirt to add a pop of brightness, embracing sky blues, sunny yellows, floral purples, and pale pinks. 

1920s Men's Fashion Shirts
1920s Men's Fashion Shirts

A French cuff shirt with gold cufflinks is evocative of the 1920’s vintage style and still readily available today. The collar can be pointed or a more rounded club-style collar.

A more casual everyday shirt was often plaid with an open collar. In the summer heat, you’d roll up your sleeves to get a bit of air, as short sleeves were only seen on sports uniforms at the time. Lighter drill cloth, khaki, sateen, or chambray were used for their breathability and comfort. In winter, wool flannel, heavy cotton, corduroy, or faux buckskin would keep the biting wind at bay. Heavier duty work shirts worn by labourers had reinforced stitching and were usually solid dark colours like grey, navy blue, olive green, or brown. That isn’t to say that plaid and stripes weren’t also available, but they weren’t as prevalent in workwear considered utilitarian above all else.


When it got cold enough that a vest and suit jacket weren’t enough to stay warm, men would reach for their knee-length overcoat. They were made of thick wool and came in plaid, solid black, gray, blue, and brown. As suits became wider and roomier, overcoats evolved alongside them. Overcoats were much larger by the end of the decade, falling to about mid-shin length, resembling a trench coat. The colour palette remained limited to black, blue-gray, or lighter tan brown. All overcoats featured deep button-flapped pockets to protect personal effects from the weather.

Overcoats weren’t the only choice, however. Black or brown fur-lined Ulster leather jackets were popular, buttoning up in the front and sometimes featuring a built-in belt cinched around the midriff. All-leather Mackinaw jackets in black or brown were durable and windproof, finding popularity amongst motorbike riders, auto racers, and pilots.

1920s Men's Fashion Coats
1920s Men's Fashion Coats

The decade’s strangest, most ostentatious coat trend was the all-fur raccoon coat, made entirely of raccoon pelts. The fad began on college campuses and was associated with young bachelors emulating sexy Hollywood extravagance. However, the style’s origin may have had to do with Davy Crocket’s semi-mythological life stories. After a high profile cover image featured on the Saturday Evening Post depicting young men wearing them, many people rushed to stores and mail-order catalogues to acquire one, despite them only wearing it for special events where they intended to be seen (usually by single ‘flappers.’)


Even without an accompanying suit jacket, a dapper V-necked waistcoat paired with a vintage style hat will lend you a good deal of jazz age swagger. The typical vest of the time featured 5 or 6 buttons, notch collar lapels, and a V-shaped neckline that perfectly framed a tie and shirt collar. A later variation had a double-breasted U-shaped neck and a gently rounded shawl-style collar. The pattern and colour could match other elements or contrast with them. Patterns were most commonly pinstripes, plaids, or subtle checks.

Winter vests were a great way to add a layer of warmth without committing to a cumbersome jacket and often came in leather, moleskin, corduroy, or heavy cotton. The WWI Army Jerkin retained some post-war popularity as a leather wool-lined vest suitable for rugged workwear.

1920s Men's Vests

The 1920s also saw the rise of pullover sweater vests, often sported by golf or tennis players. Thick cable knit vests, often in lighter shades or even snowy white, were popular with younger men. Ivy league schools popularized the iconic Argyle sweater vest and the heavier Fair Isle sweater vest, which came in both pullover and zippered styles.


Trousers in the ’20s were worn very high by today’s fashion standards. The waistband would sit above the navel, sometimes as high as just below the ribs, with a deep seat and roomy hips for comfort. In the early part of the decade, the legs would taper down from there, but they were tailored in a straight, very wide, almost baggy manner by the later years. Buttoned suspenders were used to hold them up, though more casual pants were fastened with belts threaded through wide loops by the middle of the decade. Exposed socks were worn high up the leg calf and were secured with garters (mini suspenders for your socks). They were often solid-coloured, striped, or sometimes argyle patterned.

Work pants were less fussy. Dark blue denim jeans were a hard-wearing choice, as were sturdy wool, cotton twill, and corduroy. Casual pants were wide-legged and high-waisted. A typical worker’s pants were blue, grey, tan, brown, or striped black. They featured large side pockets, as well as slit or flat pockets in the back. Casual winter pants were made of heat-retaining wool, tweed, corduroy, or moleskin. In the summer, those materials were traded in favour of flannel, light wool, or thin canvas.

1920s Men's Pants
1920s Men's Pants

Jodhpurs, originally horse riding pants, were fashionable among some men in wealthier professions. They ballooned out at the thighs to an almost comical degree before tapering down into the boots on the lower leg. In particular, they became associated with the classic movie-director ensemble, along with knee-high laced boots, a flat cap, scarf, and trusty megaphone.

The 1920s were a strange time for pants, and many of these styles appear a bit clownish in a modern context. Oxford bags (with legs up to 44 inches across at their widest) look particularly ridiculous today. It’s best to take subtle cues from the era in terms of material and pattern while leaving the unflattering baggy cuts behind. It’s the way to go if you’re looking to rock a vintage style without going for absolute authenticity.


The shape of men’s shoes gradually transitioned from a pointy almond toe that complemented slim Jazz suits to a broader square toe that mirrored the wider suits of the late decade. Oxford shoes were among the most popular and were a component of formal evening dress, especially patent leather polished to a high shine. Ornamental holes and patterns were punched into the leather, and leather tassels were sometimes added, further distinguishing them. At the end of the decade, manufacturers experimented with textured reptile-skin leather from alligators, snakes, and lizards. 

Two-toned wingtip shoes were great for casual wear, as were white nubuck shoes in summer. Nubucks were a type of leather shoe combining the best traits of suede and leather. Derby shoes were a variation on the Oxford design that had more open, less restrictive eyelet tabs (the part with the lace holes.) Traditional Oxford shoes were “straight-laced” and tight, whereas more casual derbies were looser and more comfortable to wear. 

The 1920s was also when the timeless Converse basketball shoes skyrocketed in popularity, thanks to player Chuck Taylor’s seal of approval. This made them the first in a long line of celebrity-endorsed sports shoes.

The Influence of Cars on Men’s Fashion in the 1920s

Depictions of driving in Hollywood films and newly affordable line-assembled cars contributed to the rise of the automobile as a major cultural touchstone, particularly in the United States. The fashion industry wanted in on the craze and made clothes specifically to be worn while driving a car. Savvy marketers were keen to access some of the disposable income touted by owners of fine automobiles. Indeed, some motorists spent nearly as much on their driving ensemble as they did the car itself.

So-called “motoring clothes” included flat wool or tweed English driving caps paired with vented leather gloves, leather aviator jackets, motoring goggles, and a silk scarf to whip in the wind. The outfit signalled to others that the motorist was on top of the latest trends and part of the elite group of car owners. As cars developed a closed cabin and became much more common, the phenomenon of the special motoring outfit became obsolete.

The Influence of Sports on Men’s Fashion in the 1920s

The 1920s saw sportswear entering the mainstream fashion world. In the prosperous post-war period, citizens had more time for leisure activities like sports, where they could have fun and show off their athleticism. High-profile athletes became stars, and their uniforms were emulated, particularly those of tennis, golf, and cricket players.

Tennis gave us white trousers and V-neck sweaters, often worn by younger men gallivanting around town. Golf stars popularized plus-fours (roomy, borderline baggy pants that extended four inches below the knee) with multi-coloured Fair Isle sweaters. Jodhpurs, pants mentioned above in this article, came by way of horseback riders and fencers.


Men’s hairstyles were neat and well-maintained, influenced by military grooming standards. Hair was cut short on the sides and back, fading up to a longer top that could be parted and slicked with shiny pomade or other hair tonics. A modern version of the style is the undercut, keeping a good amount of length on top for styling. The hairstyle has enjoyed a resurgence in recent years, with many well-kempt Hollywood men sporting the look. Hairstyles of the era are among the least jarring to a modern sensibility and are considered clean and timeless.

Beards were not prevalent in the West, except among older men. Those few who pushed against the status quo often kept their beards shorn close to the skin and maintained them well. Most fashionable young men opted for a totally clean shave or a thinly cropped moustache. 


Swimwear was somewhat unisex during this period, with few distinguishing features between gendered bathing suits. Both usually consisted of a ribbed wool tank top over tight shorts, fused with stitching at the waist. The top hung in a skirt-like fashion to maintain modesty, obscuring the crotch. Bright suit colours predominated, with vibrant reds, purples, yellows, and oranges. White or coloured stripes outlined the edges and skirt in the common one-piece California-style swimsuits.

By 1924, two-piece swimsuits were more widely accepted and available. The ribbed wool tank became more of a onesie that buttoned under the crotch, and separate shorts were worn over. The top had a deep scooping neckline, came in solid colours or styles, and was similarly colourful. Two-piece shorts were mid-thigh length, with a looser fit and button fly, though tighter pull-on shorts with no-fly were also available. A white webbed belt with a military-style silver buckle kept the shorts from washing away in the surf.

Many people wore all-rubber swim shoes in bright colours like red, blue, and green. Aviator-style swim caps made from rubber covered the ears and secured with an adjustable chin strap. The cap could be plain or a bright matching colour to go with the shoes and other elements.

How to Recreate the 1920’s Look

The best part of a look inspired by The Great Gatsby, Peaky Blinders, or just a love of the Jazz Age, in general, is that designers of the era were pushing the envelope with styles that were considered modern and sophisticated. The 1920s were a time when most people were focused in bright-eyed wonder toward the future, reassessing the restrictive traditions of yesteryear and adapting to a new aesthetic. The result is a range of styles that are timeless, classy, and brimming with panache. It’s the perfect amount of old vintage without going full renaissance fair.

Many roaring 20’s men’s fashions have carried forward in some form to the present, and are available from a variety of online retailers. You can go for a full suit, or mix and match vintage elements on a contemporary background. The most important part is finding the right accessories that make up the 20’s profile. Things like the right hat, a silk pocket square, two-tone Oxford shoes, or a gold pocket watch will elevate your look to the next level. To boil it down, a 1920’s vibe is all about attention to detail.

Where to Shop for the 1920’s Look

  • Amazon for almost any 1920’s outfit element. 
  • Kit Blake for quality pleated trousers/check pants.
  • Brooks Brothers provided suits for The Great Gatsby film and have all the iconic looks, despite their bankruptcy woes as a result of the pandemic. 
  • Ralph Lauren for suits that ooze 1920’s style.
  • Gucci for tuxedos and tailored Italian suits that evoke the appropriate silhouette, as well as less formal jackets.
  • MensItaly for more affordable Italian tailored suits, without a noticeable dip in quality. 
  • Rubinacci for quality 1920’s fedoras, newsboy caps, and other well-made period-appropriate hats.
  • Bollman Hat Company for wholesale and private label hats inspired by the era. 
  • Zappos for wingtip shoes, Oxfords, and boat shoes. 
  • Nordstrom has a great collection of affordable vintage shoe choices. 
  • Filson for coats, jackets, suspenders, and other accessories. 

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