If you look at a photo of a crowded New York street from 1924, you’ll notice something immediately. Every single man is wearing a hat. It’s wild. Nowadays, we think of roaring 20s style mens clothing as a flashy, gold-trimmed costume you wear to a themed New Year's Eve party, but for the guys living through the Jazz Age, it was actually about a massive cultural shift toward "cool."
Before the 1920s, men’s fashion was stiff. It was formal. It was basically designed to make you look like a Victorian statue. Then the war ended, the music got faster, and suddenly, men wanted to move. They wanted to dance the Charleston without their high collars choking them.
The suit that changed everything
The backbone of the era was the sack suit. Honestly, it wasn't nearly as baggy as the name implies, but compared to the frock coats of the 1910s, it felt like wearing pajamas. These suits featured natural shoulders and a much more relaxed fit through the torso.
You’ve probably seen the three-piece look in shows like Peaky Blinders. While that show is set slightly earlier and in the UK, the silhouette transitioned perfectly into the American 1920s. The waistcoat (or vest) was mandatory. You didn't just walk around in a shirt; that was considered "underdressed," almost like being in your underwear. The vest kept everything tucked in and provided a handy place for your pocket watch, though wristwatches were starting to gain some serious ground after soldiers found them useful in the trenches.
Fabrics were heavy. We're talking wool, tweed, and flannel. Even in the summer, these guys were layering up. But they played with patterns in a way that would make a modern minimalist's head spin. Pinstripes, windowpane checks, and herringbone were everywhere. It wasn't about being subtle; it was about showing you had the scratch to afford a decent tailor.
Those massive pants
One of the weirdest things most people get wrong about roaring 20s style mens outfits is the "Oxford Bag."
Legend has it these started at Oxford University because the school banned knickerbockers in the classroom. The students, being rebellious, just made incredibly wide-legged trousers to slide over their forbidden knickers. We are talking pant legs that could be 22 to 40 inches wide at the bottom. It looks a bit ridiculous by today's standards—kinda like the JNCO jeans of the 1920s—but it became a massive trend for the youth.
Most regular guys stuck to "plus-fours." These were baggy trousers that ended four inches below the knee, usually worn for golf or sporting events. They were the ultimate "I'm on vacation" vibe of the 1920s.
The accessories that actually mattered
You couldn't leave the house without a hat. Period.
If you were a working-class guy or just hanging out on the weekend, you wore a newsboy cap or a flat cap. If you were headed to the office, you grabbed a Fedora or a Homburg. In the summer? The Boater hat. Those stiff, straw hats with the ribbon were the uniform of the seaside. They’re incredibly uncomfortable—basically like wearing a wicker basket on your head—but they looked sharp.
- Detachable collars: Most shirts didn't have collars sewn on. You had a bunch of white collars you’d starch until they were stiff as cardboard and then stud them onto your shirt. This meant you could wash the collar (which got dirty fast) without washing the whole shirt.
- Two-tone shoes: Spectator shoes are the hallmark of the decade. Usually white and brown or white and black. They scream "Jazz Age."
- Neckties: This was the decade the "four-in-hand" knot became the king. Ties became colorful, featuring Art Deco geometric patterns that mirrored the architecture of the time.
Why the look still works today (Sorta)
Believe it or not, we’re seeing a massive resurgence in 1920s silhouettes, though they’re muted. High-waisted trousers are back in style because they make your legs look longer and your waist look slimmer. Modern "slim fit" is actually dying out in favor of the wider, straighter leg that dominated the late 20s.
The real trick to pulling off roaring 20s style mens fashion today without looking like you’re in a play is to pick one element. Don't do the hat, the vest, the tie, and the shoes all at once. If you wear a well-tailored tweed waistcoat over a modern button-down, you've nailed the vibe. If you opt for a wider-leg trouser with a cuff at the bottom, you’re channeling the era's spirit.
The "Gatsby" Myth
We have to talk about F. Scott Fitzgerald and the 2013 movie. While the movie was a visual masterpiece, it took a lot of liberties. The neon colors and super-slim fits were more "2013 tries the 1920s" than actual history. Real 1920s suits were boxier. The colors were earthier—browns, grays, tans, and navy. If you want to dress like the real Jay Gatsby, look for a "Palm Beach" suit in a light linen or seersucker. That was the true mark of wealth: wearing something that could easily get dirty because you didn't have to work.
Breaking down the formal wear
Evening wear was where things got serious. The tuxedo (or dinner jacket) was starting to replace the formal tailcoat for most social events. It was a time of transition. If you were going to a "Black Tie" event in 1926, you'd be wearing a stiff-fronted shirt with wing collars and a bow tie.
The fabrics were midnight blue or black. Midnight blue was actually preferred because, under artificial light, it looked "blacker" than black itself, which could sometimes look a bit dusty or grey.
How to build a 1920s inspired wardrobe
If you're actually looking to incorporate this into your life, start with the textures.
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- Invest in a heavy-weight wool blazer. It needs to feel substantial.
- Find trousers with a higher rise. They should sit at your natural waist, near your belly button, not on your hips.
- Get a pair of brogues. Look for something with heavy perforations.
- Try a knit tie. They were popular for more casual looks back then and they add a great texture to a modern suit.
The 1920s were about optimism. People were recovering from a global pandemic (the Spanish Flu) and a world war. They wanted to look like the future. Even though the styles feel "vintage" to us, they were the "cutting edge" back then. It was the birth of the modern man.
Actionable Next Steps for the Modern Man
To bring this aesthetic into the 2020s, focus on the "Speakeasy" look. This involves mixing rugged textures with formal pieces. Swap your denim jacket for a herringbone wool "chore" coat. Replace your sneakers with a pair of leather dress boots. Most importantly, pay attention to the fit of your trousers; a little extra room in the leg and a higher waistline will immediately give you that 1920s authority without the need for a costume shop.
Focus on quality over quantity. The men of the 20s didn't have fifty outfits; they had four or five very high-quality ones that were repaired and kept for years. That's a lesson in sustainability that's just as relevant now as it was a hundred years ago.
For those looking to source authentic pieces, search for "vintage-style heritage workwear" or "revival tailoring." Brands specializing in these areas often use the heavier fabric weights and higher-waisted patterns that define the era. Avoid the "costume" section of major retailers, as these garments are usually made of thin polyester that won't drape correctly or breathe, ruining the sharp, structured silhouette that made the original roaring 20s style mens fashion so iconic. Instead, look for 100% wool or linen options that provide the natural drape and longevity required for a true period-accurate look.