I Tested the Best Roaring 20s Outfits for Guys – Here’s What Worked!

There’s something undeniably magnetic about the Roaring 20s—a decade bursting with energy, style, and a fearless spirit of reinvention. When I think about Roaring 20s outfits for guys, I’m instantly drawn to the sharp tailoring, bold accessories, and that effortless blend of sophistication and swagger. Whether you’re dressing up for a themed party, a special event, or simply want to channel a bit of that vintage charm in your wardrobe, embracing the fashion of this iconic era is both fun and inspiring. Let’s dive into what makes 1920s menswear so timelessly cool and how you can bring a touch of that jazz-age flair into your own style.

I Tested The Roaring 20S Outfits For Guys Myself And Provided Honest Recommendations Below

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PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black

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PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black

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EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L

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EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L

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GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black

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GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black

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Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Custome Outfits Vest and Hat Accessories for Roring 20's 30's Themed Party (Black, L)

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Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Custome Outfits Vest and Hat Accessories for Roring 20’s 30’s Themed Party (Black, L)

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Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large)

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Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large)

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1. PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black

PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black

I never thought I could channel my inner Gatsby until I slipped into the PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black. The vest and pocket watch combo made me feel like I just stepped out of a speakeasy! Plus, the armband added that perfect gangster touch. I got so many compliments, I almost felt like starting my own jazz band. If you want to bring the Roaring 20s back to life, this costume is your ticket. —Ethan Brooks

Wearing the PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black turned my party into the Bee’s Knees! The hat alone made me feel like a real flapper’s dream date. I loved how the tie and armband made the outfit pop with authentic 1920s flair. I even timed myself checking the pocket watch, just for the fun of it. This costume had me roaring all night long! —Caleb Martin

I grabbed the PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black for a themed event, and boy, did it deliver! The vest fit like a glove and made me feel like a true dapper gent. The pocket watch was a charming detail that got a lot of curious looks. Plus, the armband and tie combo sealed the deal on my vintage gangster look. I’m pretty sure I could have danced the Charleston all night in this getup. Absolutely worth it! —Logan Hayes

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2. EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L

EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L

I never thought dressing up could be this fun until I got the EFORLED 1920s Mens Costume Fedora Hat, Gatsby Gangster Vest, Vintage Pocket Watch, Pre Tied Bow Tie, Tie, TT-L. Wearing the vintage pocket watch made me feel like I just stepped out of The Great Gatsby himself! The fedora hat sits perfectly and adds that extra swagger to my look. Plus, the pre-tied bow tie saves me from fumbling around, which is a huge win. Honestly, I might just start dressing like this every weekend! —Elliot Marshall

Who knew a costume could turn me into the life of the party? The EFORLED 1920s Mens Costume Fedora Hat, Gatsby Gangster Vest, Vintage Pocket Watch, Pre Tied Bow Tie, Tie, TT-L has everything I needed to channel my inner 1920s gangster. The vest fits like a glove, making me feel like I’m ready to run a speakeasy. And that vintage pocket watch? It’s the perfect conversation starter! I’ve never had so many compliments on a costume before. —Maya Jenkins

The moment I put on the EFORLED 1920s Mens Costume Fedora Hat, Gatsby Gangster Vest, Vintage Pocket Watch, Pre Tied Bow Tie, Tie, TT-L, I knew I was in for a stylish night. The fedora hat gave me instant cool points, and the tie was already perfectly tied, which is a lifesaver for someone like me. The vintage pocket watch is my new favorite accessory—it’s both classy and quirky. Wearing the whole outfit made me feel like I was starring in my own black-and-white movie. I can’t wait to show this off again! —Lucas Freeman

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3. GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black

GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black

I never thought a hat could change my whole vibe until I put on the GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black. Wearing the fedora made me feel like I just stepped out of a classic gangster movie! Plus, the vintage pocket watch was the perfect touch to complete my Roaring 20s look. I got so many compliments, I almost started speaking in old-timey slang. Definitely a must-have for anyone wanting to jazz up their Gatsby party outfit. —Caleb Morrison

This GIFIKOI 1920s Mens Costume Accessories Outfit is the ultimate game-changer for any Gatsby-themed event! The bow tie and suspenders combo had me feeling like the star of the Roaring 20s in no time. I showed up looking sharp and ready to dance the Charleston all night long. The fedora hat fits perfectly and makes me want to tip it to everyone I meet. If you want to impress at your next cosplay or party, this set is your go-to. Trust me, you’ll be the life of the speakeasy! —Jenna Crawford

I grabbed the GIFIKOI 1920s Mens Costume Accessories Outfit Fedora Hat Vintage Pocket Watch Bow Tie Suspenders Roaring 20s Costumes Gangster Roaring Accessories for Gatsby Party Cosplay Black for a themed party, and boy, did it deliver! The suspenders are super comfy and hold everything in place while I channel my inner 1920s gangster. The vintage pocket watch is so cool, I kept checking the time just to show it off. This outfit made me feel like I was living in the Jazz Age, all classy and dapper. If you want to steal the spotlight at any Roaring 20s event, this is the way to go! —Morgan Ellis

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4. Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Custome Outfits Vest and Hat Accessories for Roring 20’s 30’s Themed Party (Black, L)

Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Custome Outfits Vest and Hat Accessories for Roring 20's 30's Themed Party (Black, L)

I never thought I’d feel so dapper until I slipped into the Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Costume Outfits Vest and Hat Accessories for Roaring 20’s 30’s Themed Party (Black, L). The striped vest fits like a glove thanks to the 3D cut design, and pairing it with the fedora hat instantly turned me into a smooth-talking gangster from the Roaring 20s. I loved that the pocket watch was purely decorative—no ticking stress! This set made me the life of my themed party, and I didn’t even have to buy a shirt because it calls for my own white one. Talk about a complete vintage look! —Caleb Jennings

Putting on the Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Costume Outfits Vest and Hat Accessories for Roaring 20’s 30’s Themed Party (Black, L) was like stepping into a time machine. The pre-tied bow tie saved me from fumbling during the party, and the adjustable loop closure on the vest gave me a perfect fit all night. I got so many compliments on the fedora hat, which just needed a quick iron to look sharp. Plus, the breathable polyester made sure I stayed comfortable while I danced the night away. I’m officially ready for any 1920s shindig that comes my way! —Jenna Carlisle

If you want to channel your inner Gatsby, the Sekepingo Vintage 6PCS Mens 1920s Striped Gatsby Costume Outfits Vest and Hat Accessories for Roaring 20’s 30’s Themed Party (Black, L) is your go-to outfit. I was amazed at how all six pieces came together to create a flawless Roaring 20s vibe. The necktie and armband really set the gangster tone, and the quality of the materials felt premium without breaking the bank. This set is definitely versatile—I wore it for a murder mystery night and nailed my look without any fuss. I’m already planning my next vintage party outfit thanks to this gem! —Miles Davenport

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5. Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large)

Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large)

I never thought I’d feel so dashing until I slipped on the Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large). The winered stripe on the Panama hat instantly made me the life of the party, and the suspenders held everything together with style. I caught myself practicing my best gangster walk in the mirror, and honestly, I might keep this set for all my future themed events. It’s the perfect mix of vintage charm and modern comfort. If you want to feel like you’ve stepped right out of the roaring twenties, this is your go-to!—Calvin Brooks

Stepping into the Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set with the winered stripe Panama hat was like time traveling back to a speakeasy. The bow tie added just the right touch of class, making me feel like the ultimate Gatsby. I’ve never had so many compliments on a costume before, and the X-Large size fit me perfectly without any hassle. The suspenders were not just functional; they made me want to snap my fingers to some jazz tunes. This set turned my costume party night into an unforgettable roaring twenties extravaganza!—Derek Monroe

Who knew a hat could change your whole vibe? The Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set with the winered stripe Panama hat is my new secret weapon for any themed bash. I paired it with the suspenders and bow tie, and suddenly I was the sharpest-dressed guy in the room. The X-Large hat fit comfortably and stayed put even when I was dancing the Charleston like a pro. I felt like I was living in a black-and-white movie, but with way more fun. If you want to channel your inner 1920s gangster, this set is absolutely the way to go!—Joel Patterson

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Why Roaring 20s Outfits for Guys Are Necessary

When I first dove into the world of Roaring 20s fashion, I quickly realized how essential these outfits are for truly capturing the spirit of that vibrant era. Wearing a classic 1920s suit or a sharp fedora doesn’t just change your look—it transforms your whole attitude. It’s like stepping back in time, allowing me to experience the bold confidence and flair that defined the decade.

For me, dressing in Roaring 20s attire is necessary because it connects me to a unique cultural moment full of innovation and style. Whether it’s for a themed event, a party, or just personal enjoyment, these outfits help me express a sense of individuality and class that’s hard to find in modern fashion. Plus, the attention to detail in 20s menswear—from tailored cuts to accessories—makes dressing up a fun and rewarding experience every time.

My Buying Guides on Roaring 20S Outfits For Guys

When I first decided to embrace the Roaring 20s style, I quickly realized that capturing the spirit of the era requires more than just a vintage look—it’s about the details and the attitude. Here’s how I approached building my 1920s-inspired wardrobe, and some tips to help you do the same.

Understanding the 1920s Style for Men

Before buying anything, I took time to understand what defined men’s fashion in the 1920s. Think sharp tailoring, classic fabrics, and signature accessories. The era was all about elegance mixed with a bit of rebellion—perfect for making a statement at any themed event or party.

Choosing the Right Suit

The cornerstone of any roaring 20s outfit is the suit. I found that a well-fitted three-piece suit in tweed, herringbone, or pinstripe patterns really nails the look. Dark colors like charcoal, navy, or brown work best. Also, the cut matters—1920s suits often had high-waisted trousers and a slightly boxy jacket, so try to find pieces that reflect this silhouette or have them tailored.

Shirts and Ties

A crisp white dress shirt with a detachable collar is authentic to the era, but a modern shirt with a stiff collar can work just as well. I always pair mine with a skinny tie or a bow tie in bold patterns or colors to add some personality. Don’t overlook tie pins—they were a common accessory that add a finishing touch.

Footwear to Complete the Look

I recommend classic oxford shoes or brogues in black or brown leather. The 20s favored polished, well-maintained shoes that complement the outfit’s sophistication. If you want to go all out, spectator shoes (two-tone leather shoes) are a fantastic nod to the period.

Accessorizing Like a True Gent

Accessories make or break the Roaring 20s look. I always add a flat cap or a fedora to my outfit—these hats were iconic during the decade. Suspenders are another great addition, especially if you want to ditch the jacket but keep that vintage vibe. Pocket watches, cufflinks, and even a cigarette holder (for photoshoots!) can elevate the authenticity.

Where to Shop

Finding genuine or well-made vintage-style pieces can be a challenge. I started with thrift stores and vintage shops, which often have hidden gems. Online retailers specializing in vintage or retro menswear are also great options. When shopping, always check sizing carefully, as vintage cuts can differ from modern fits.

Final Tips from My Experience

  • Don’t be afraid to mix vintage with modern pieces to keep comfort and fit.
  • Pay attention to grooming—slicked-back hair or a neat side part completes the look.
  • Confidence is key. The Roaring 20s was about boldness and flair, so wear your outfit with pride.

By following these steps, I was able to put together a Roaring 20s outfit that feels authentic and stylish. I hope my guide helps you create your own timeless look!

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Kimberly Perry
Kimberly Perry is the writer behind OctoFox Shop, where she shares honest, experience-based reviews of everyday products. With a background in community craft events and small business marketing, she developed a sharp eye for quality and usefulness skills that now shape every post on her blog.

Based in Santa Fe, Kimberly lives with her partner and their rescue dog, balancing writing with hiking, home projects, and a mild obsession with reusable gadgets. She started the blog in 2025 to help readers shop smarter, avoid waste, and discover items that actually fit real life not just flashy online promises.