Forget the neon-lit, synthetic costumes you see at every "Jazz Age" themed office party. Most of that stuff is total fiction. When people think about roaring twenties men's fashion, they usually picture Leonardo DiCaprio in a pink suit or some guy in a cheap polyester vest with a plastic Tommy gun.
It was actually much weirder. And much more structured.
The 1920s didn't just happen; they exploded. After the carnage of World War I, men were basically done with the stiff, high-collared formality of the Edwardian era. They wanted to breathe. They wanted to move. But they weren't wearing t-shirts and jeans yet. Instead, they invented a middle ground that was somehow both incredibly sharp and wildly experimental.
The Oxford Bags Obsession
Have you ever seen pants so wide they look like a skirt? That’s not a joke. In 1924, students at Oxford University started wearing "Oxford Bags." These were trousers with leg openings that sometimes reached 40 inches in circumference.
Why?
Legend has it they were trying to hide their knickerbockers underneath because the university banned them in classrooms. It was a classic "screw you" to authority. The trend crossed the Atlantic, and suddenly, American Ivy League kids were waddling around in massive flannel tents. It was the first real "youth culture" fashion movement in the modern sense. These weren't your dad’s trousers. They were baggy, high-waisted, and frequently triggered angry editorials in newspapers claiming the youth had lost their minds.
The suit that changed everything
Before the war, a man’s suit was essentially a uniform of social standing. It was heavy. It was dark. By the mid-20s, the "sack suit" became the standard. This was a shorter, more natural-fitting jacket that didn't have the heavy padding of previous generations.
Honestly, the silhouettes were kind of boxy.
If you look at old photos from the Sears, Roebuck & Co. catalogs from 1927, you’ll notice the shoulders are soft. The lapels were getting wider, often peaked, and the buttons were placed higher up on the torso. This gave men a sort of barrel-chested, athletic look that was very popular as sports like tennis and golf became the new status symbols.
Fabrics Were a Literal Heavy Lift
We're spoiled today. We have lightweight wool and "performance" fabrics. In 1922, if you were wearing a suit, you were wearing like ten pounds of wool.
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Tweed was the king of the outdoors. It was scratchy. It was thick. But it was indestructible. For the city, men wore heavy worsted wools in patterns that would make a modern minimalist faint. We’re talking bold windowpane checks, thick pinstripes, and the "Prince of Wales" glen plaid.
Colors were surprisingly diverse too.
While navy and charcoal were the bread and butter for business, the weekends were for "ice cream" colors. Browns, tans, and even shades of soft blue or sage green started appearing in the summer months. Linen became the go-to for the wealthy vacationing in Palm Beach or the French Riviera. If you were a guy in 1926, you likely owned one heavy navy suit for church and funerals, and a couple of lighter, patterned suits for literally everything else.
The collar revolution
You’ve probably seen those tiny gold bars pinning a shirt collar together. That wasn't just for style. Early in the decade, detachable collars were still common. They were made of starched linen or even celluloid (which was basically plastic and, fun fact, highly flammable). They were stiff as a board and incredibly uncomfortable.
Then came the "soft collar."
Arrow Shirts—famous for their "Arrow Collar Man" advertisements illustrated by J.C. Leyendecker—began pushing shirts with collars already attached. This was a massive shift. It signaled a move toward comfort. To keep these new, softer collars from flopping around, men used collar pins and bars. It gave them that crisp, pointed look without the feeling of being strangled by a piece of cardboard.
Hats: The Non-Negotiable Accessory
You didn't go outside without a hat. Period. If you did, people probably thought you’d been robbed or were having some kind of mental breakdown.
The social rules for hats were intense:
- The Fedora: This was the all-purpose workhorse. Usually felt, with a wide brim and a pinched crown.
- The Newsboy Cap: Also called a flat cap or an eight-panel. This wasn't just for kids selling papers. It was the "sporty" choice for driving your Model T or heading to a baseball game.
- The Boater: A stiff straw hat with a flat top and a ribbon. These were strictly for summer. There was even a "Straw Hat Day" in many cities—usually in May—where men collectively switched from felt to straw.
- The Homburg: A bit more formal than the fedora, with a curled edge to the brim. Think gangsters or high-level bankers.
The "Hatters' Gazette" from the era is full of frantic articles about the importance of maintaining your brim's shape. It was a whole industry of maintenance.
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What Most People Get Wrong About the Footwear
People think everyone wore "spectator shoes"—those two-tone white and black wingtips. In reality, those were considered pretty flashy. Most men wore solid brown or black leather boots or oxfords.
The "Cap Toe" Oxford was the definitive shoe of the 1920s.
It was simple, elegant, and meant to be polished until you could see your reflection in it. Workboots were still very much boots—high-laced and made of thick cowhide. But for the middle-class man, the transition from boots to "shoes" (low-cut oxfords) was a major part of the decade's fashion identity. It made the ankles visible, which necessitated another fashion staple: the patterned sock.
Geometric patterns, clocks (embroidery on the side), and bright colors were suddenly everywhere. If your pants were short enough to show your socks, those socks better look expensive.
The Sportswear Explosion
Golf changed everything for roaring twenties men's fashion.
Before the 20s, men didn't really have "activewear." You just wore an older suit to do physical stuff. But the 1920s brought us the "Plus-Fours." These were knickers that dropped four inches below the knee. They were baggy, comfortable, and paired with wildly patterned Fair Isle sweaters.
Fair Isle became a massive trend after the Prince of Wales (the future Edward VIII) wore one in public in 1922. Suddenly, every guy wanted a hand-knitted sweater with complex, multi-colored geometric patterns. It was the 1920s version of a hypebeast drop.
Outerwear and the "Raccoon Coat"
If you were a college student in 1928, you probably wanted a raccoon coat. These things were massive, shaggy, and incredibly expensive. They became a symbol of the "Jazz Age" youth, often seen in the stands at football games or stuffed into the back of a Packard. They were heavy, smelled slightly like a wet dog when it rained, and were eventually parodied to death. But for a few years, they were the ultimate status symbol of the American male student.
Evening Wear Was Still Rigid
While daytime fashion was loosening up, the evening was still a fortress of tradition. The tuxedo (or dinner jacket) was becoming more common than the full "white tie and tails" for social gatherings, but the rules were strict.
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A tuxedo had to be black or midnight blue. The shirt had to be starched, usually with a pleated or "pique" front. The bowtie had to be silk. If you showed up in a "creative" tuxedo back then, you weren't being trendy—you were just wrong.
However, we did see the rise of the "silk lounge robe." Wealthy men would change into these elaborate, deco-patterned robes at home to smoke and drink. It was the peak of "at-home" luxury.
Why Does This Still Matter Today?
You can see the DNA of the 1920s in almost every modern "classic" menswear shop. The high-waisted trouser is currently making a massive comeback. The idea of the "capsule wardrobe" basically started here, where a man would have a specific set of items for specific times of day.
The 1920s taught men that they could be comfortable without looking like a slob. It was the birth of the "casual" man, even if his version of casual still involved a tie and a hat.
How to apply 1920s style without looking like you're in a costume
If you want to pull from this era, don't buy a 1920s costume. Look for the details:
- High-Rise Trousers: Look for pants that sit at your natural waist (near the belly button), not your hips.
- Texture Over Shine: Choose matte flannels, tweeds, and linens instead of shiny synthetic blends.
- Pattern Mixing: Don't be afraid to wear a striped shirt with a patterned tie, as long as the scale of the patterns is different.
- The Knit Vest: A solid or Fair Isle vest under a blazer is a direct nod to the mid-20s "inter-war" look.
- Cuffs: Ask your tailor for a 1.75-inch or 2-inch cuff on your trousers. It adds weight and looks period-accurate.
The real secret to the 1920s wasn't the flash; it was the silhouette. It was a decade of transition from the Victorian "man-as-statue" to the modern "man-on-the-move." It was messy, experimental, and occasionally ridiculous (looking at you, Oxford Bags), but it set the stage for everything we wear now.
Take a look at the Ralph Lauren "Polo" aesthetic or the high-end tailoring of brands like Drake’s or Anderson & Sheppard. They are still riffing on the shapes and textures perfected between 1920 and 1929. The era didn't just roar; it rewrote the rulebook.
To truly master this look, focus on the fit of the waistcoat and the break of the trouser. Avoid the "shiny" fabrics found in cheap modern suits. Seek out a vintage-style spearpoint collar shirt if you really want to commit. Most importantly, remember that the men of that era dressed for their peers and their profession, not just for a photograph. The clothes were functional tools of social navigation. That’s a philosophy that never actually goes out of style.