You’ve seen the photos. Everyone thinks 1920s men's fashion was just a sea of pinstripe suits and Tommy guns. Honestly, that's mostly Hollywood talking. If you're looking for roaring 20s outfits for guys, you’ve probably realized that most costume shops sell cheap, polyester garbage that looks nothing like what men actually wore during the Jazz Age.
The 1920s represented a massive shift. Before the Great War, men were basically stiff boards in high collars. Then, everything changed. Soldiers came home wanting comfort. They wanted to move. They wanted to dance. This decade was the literal birth of "sportswear" as we know it today.
The Suit That Changed Everything
If you want to nail the look, you have to understand the silhouette. Forget your modern slim-fit suits. In the early 20s, suits were still pretty snug—what they called "jazz suits"—but as the decade progressed, things got wider. Much wider. By 1925, the "Oxford Bag" had arrived. These trousers were massive, sometimes reaching 22 inches or more at the hem. Why? Because students at Oxford University weren't allowed to wear knickerbockers to class, so they wore giant pants over them to hide the "illegal" attire.
The fabric mattered too. You weren't wearing thin, breathable wool. You were wearing heavy, scratchy, 14-ounce wool that could practically stand up on its own. It stayed in place. It looked sharp even after a night of drinking illegal gin.
Patterns That Scream 1920s
Don't just go for black. Black was for funerals and evening wear. If you want to look authentic, look for:
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- Herringbone: That classic V-shape weave.
- Windowpane Check: Big, bold squares.
- Glen Plaid: Often called Prince of Wales check.
- Fair Isle: For those chunky sweaters that every "sporty" guy wore on the weekends.
Forget the Fedora (For a Minute)
Everyone reaches for a fedora. It’s the default. But if you were a working-class guy or just hanging out on a Saturday, you were wearing a Newsboy cap. Or a flat cap. They’re basically the same thing but constructed slightly differently. Eight panels of wool with a button on top—that was the uniform of the streets.
If it was summer, you wore a Boater. You know, those stiff straw hats with the flat tops? They were everywhere. In fact, there used to be a thing called "Straw Hat Day" in New York. If you wore your straw hat past September 15th, people would literally snatch it off your head and stomp on it. People took their headwear seriously back then.
The Secret is in the Shirt
Most guys mess up the collar. In the early 20s, detachable collars were still a thing. They were stiff, white, and connected to the shirt with little brass studs. It was a pain. But as the decade rolled on, the "soft" collar took over.
Think about the "Spearpoint" collar. It’s long. It’s pointy. It looks incredible with a collar bar—that little gold stick that clips both sides of the collar together and pushes your tie knot out. It gives you that specific, elevated look that screams Boardwalk Empire. If your collar isn't pinned or buttoned down, you’re just a guy in a modern suit.
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Shoes: Two-Tone or Bust
Let's talk about Spectator shoes. You’ve seen them—white in the middle, brown or black on the toes and heels. They were the ultimate "I have money and I don't work in a factory" flex. If you're putting together roaring 20s outfits for guys, a pair of wingtips is your safest bet. But please, for the love of everything, make sure they’re leather. No square toes. Ever.
The Great Gatsby vs. The Peaky Blinder
There are two main "vibes" most guys go for. You’ve got the Gatsby look: light-colored linens, pink suits (yes, Jay Gatsby wore a pink suit), and white silk ties. This is "old money" (or at least faking it).
Then you have the Peaky Blinder look. This is the heavy wool, the dark greys, the waistcoats, and the sturdy boots. It’s rugged. It’s "don't mess with me." Both are historically accurate, but they serve different purposes. If you're heading to a summer garden party, go Gatsby. If you're hitting a basement speakeasy, go Peaky.
Accessories You Actually Need
- Pocket Watches: Wristwatches were "trench watches" and were just starting to become popular, but a gold chain across your vest still looked better.
- Arm Garters: Those little metal bands you wear on your biceps. They kept your sleeves the right length since shirts didn't come in 50 different sizes back then.
- Cufflinks: Not the flashy diamond ones. Simple enamel or gold.
- Silk Scarves: Worn tucked into an overcoat. It wasn't just for warmth; it was for style.
Real Examples from the Archives
Look at photos of Douglas Fairbanks or the Prince of Wales from 1926. The Prince was a style icon. He’s the one who popularized the Windsor knot (sorta) and the Fair Isle sweater. He took the stiffness out of men’s fashion. He wore things that looked comfortable.
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Contrast that with the "G-Men" or the bankers of the time. They were still clinging to the high-waisted, pleated trousers and the dark sack suits. The 20s was a battle between the old Victorian leftovers and the new, rebellious youth culture.
Common Mistakes to Avoid
Don't wear a clip-on bowtie. Just don't. It looks like you're five years old. A real bowtie has a slight asymmetry to it that makes it look authentic. Also, avoid anything with a zipper. Zippers existed, but they weren't used in trousers until the 1930s. If you want to be a purist, it's buttons all the way down.
Another big one: the waistcoat (vest). A 1920s vest was cut high. It didn't show much of the tie. If your vest is cut low like a modern tuxedo vest, it’s going to look wrong. And remember to leave the bottom button undone. That’s a tradition that started with King Edward VII because he was too fat to button his, and it stuck.
Why Quality Matters
Most "costume" versions of roaring 20s outfits for guys use thin, shiny materials. In 1924, if your suit was shiny, it meant it was old and worn out. You want matte. You want texture. Go to a thrift store and look for heavy vintage blazers. Find things with wide lapels—peaked lapels were especially popular for a more formal or "tough" look.
Actionable Steps for Your 20s Wardrobe
If you are building an outfit today, don't buy a pre-packaged costume. You'll regret it. Instead, follow this checklist to build a kit that you can actually wear again.
- Find the Trousers First: Look for high-waisted, wide-leg wool trousers. They should sit at your natural waist (near your belly button), not your hips. This is the most important part of the silhouette.
- Get a Waistcoat: It doesn't have to match the pants perfectly. A "broken suit" (different jacket and pants) was very common in the 20s.
- The Shirt: Buy a white or striped tunic shirt with a club collar (rounded edges). Add a collar bar for extra credit.
- The Hat: Decide on your vibe. Flat cap for the working man, Boater for the dandy, or a Fedora for the businessman.
- Suspenders (Braces): Never wear a belt with a suit in the 20s. Use button-on suspenders. If your pants have belt loops, cut them off or hide them.
Building an authentic look takes a bit of digging, but the result is a style that feels grounded and masculine. The 1920s wasn't just about looking "fancy"—it was about the first generation of men finally breaking free from the suffocating rules of the 19th century. Wear it with that kind of confidence.