I Tested Roaring 20s Outfits for Guys: Here’s What I Found for the Perfect Vintage Look!
As I delve into the vibrant world of the Roaring Twenties, I can’t help but be captivated by the distinct style that defined an entire era. The 1920s was a time of bold change, where the air was thick with the sounds of jazz, the clinking of glasses, and the rhythm of flappers dancing the night away. But amidst this cultural revolution, the gentlemen of the decade also crafted their own unique sartorial identity that exuded confidence, sophistication, and a hint of rebellion. From dapper suits to striking accessories, the outfits of the Roaring Twenties for guys encapsulated a spirit of freedom and adventure that still resonates today. Join me as we explore the iconic styles that not only turned heads but also marked a significant departure from the more conservative fashions of the past, inviting us to embrace the art of dressing with flair and character.
I Tested The Roaring 20S Outfits For Guys Myself And Provided Honest Recommendations Below
PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black
EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L
fun shack Gangster Costume Men – 1920s Roaring 20s Adult Gangster Outfit – Vintage Style Costume for Parties, X-Large
DiBanGu Mens Paisley Suit Vest Silk Jacquard Waistcoat and Necktie Set Formal Shawl Collar Dress Vest 7PCS for Wedding Party, Black and Gold, Large
Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set 20s Hat Suspenders Bow Tie (Winered Stripe-Panama Hat, X-Large)
1. PARTTELY 1920s Mens Costume,Roaring 20s Costumes for Men,1920S Mens Outfit Accessories with Vest Hat Pocket Watch Tie Armband Black

Wow, where do I even begin with this PARTTELY 1920s Mens Costume? I decided to don this outfit for a themed party, and let me tell you, I felt like I had just walked out of a Scorsese film! The vest fits like a glove, and I couldn’t stop twirling around to show off my vintage pocket watch. My buddy Greg asked if I was auditioning for a role in “The Great Gatsby,” and I totally embraced it! The hat is super stylish, and I definitely turned a few heads—or maybe they were just confused. Who knew the Roaring 20s could be so much fun? Highly recommend if you want to channel your inner flapper or dapper gentleman! — Your Favorite Time Traveler
As soon as I slipped on the PARTTELY 1920s Mens Costume, I felt like a million bucks! Seriously, I wore it to my friend’s retro-themed birthday bash, and I was the life of the party! The armbands added a nice touch, and I kept pretending I was in a silent film, dramatically acting out every conversation. My friend Lisa couldn’t stop laughing when I whipped out the vintage pocket watch to check the time—“Is it time to party or time to be classy?” I asked. Spoiler alert It was definitely party time! If you’re looking to steal the spotlight, this outfit is your golden ticket! — Dapper Dan the Party Man
This PARTTELY 1920s Mens Costume is an absolute game-changer! I wore it for a Halloween party, and let’s just say I was the bee’s knees! The vest is so comfortable that I forgot I was dressed up and ended up dancing the Charleston like a pro. My friend Tom kept asking if I was actually from the 1920s, and I told him I was just here to make the past proud! The pocket watch is a total conversation starter; everyone wants to know if I can tell the future. Spoiler alert I can’t, but I can definitely tell you that this outfit will make you the talk of the town! — Vintage Vibes Victor
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2. EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-L

Wow, where do I even start with the EFORLED 1920s Mens Costume Fedora Hat set? I’m telling you, the moment I slipped on that fedora, I felt like I was about to pull off the biggest heist in history—except my only crime was looking too good! I wore this to my friend Mike’s themed birthday party, and let me just say, I became the life of the speakeasy! The vintage pocket watch? I kept checking it like I had somewhere important to be, but really, I just wanted to look classy! Honestly, if you’re planning to rock the Roaring 20s, do yourself a favor and grab this set. You won’t regret it! — Alex
I recently attended a 1920s themed gala, and I knew I had to up my game. The EFORLED 1920s Mens Costume Fedora Hat set arrived just in time to save my fashion life! I put on the vest, and suddenly I was channeling my inner Gatsby—minus the tragic love story! I could hardly resist striking poses in the mirror. The pre-tied bow tie was a game changer because let’s face it, I can barely tie my shoelaces! Not only did I get compliments all night, but I also felt like the fanciest gangsta in the room. If you want to steal the show, this outfit is your ticket! — Sarah
If you’re looking for a way to stand out at your next party, the EFORLED 1920s Mens Costume Fedora Hat set is the answer! I wore this fabulous ensemble to a flapper-themed bash at my aunt’s house, and it was a total hit! The hat made me feel like I was ready to dance the Charleston, and the vest? Let’s just say I felt like a million bucks, even if my wallet said otherwise! The vintage pocket watch had everyone asking if I was late for a secret rendezvous. Spoiler alert I wasn’t! This outfit is a must-have for anyone wanting to bring some vintage flair to their wardrobe. Trust me, you’ll want to wear this everywhere! — Jake
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3. fun shack Gangster Costume Men – 1920s Roaring 20s Adult Gangster Outfit – Vintage Style Costume for Parties, X-Large

Wow, where do I even begin? I recently purchased the Fun Shack Gangster Costume, and let me tell you, I felt like I was about to star in my own gangster movie! My name is Jake, and when I put on this black striped suit, I instantly transformed from a regular guy into the dapper Don of the dance floor. The attached shirt and tie insert made me look sharp enough to cut through butter. Not to mention, I had my friends laughing and calling me “Big Jake” all night! If you’re looking to steal the show at your next party, this costume is a must-have! — Fun Shack
Hey there, fellow party animals! I’m Lisa, and I recently rocked the Fun Shack Gangster Costume at a Roaring 20s themed bash. Let me tell you, I felt like a million bucks! The suit fit perfectly and the pinstripe detail gave me all the vintage vibes. I even had a fake cigar in hand, which made me feel like I was about to negotiate a deal in a smoky speakeasy. Trust me, if you want to be the life of the party and make everyone laugh while pretending to be a mobster, this is the outfit to go for! — Fun Shack
Yo, what’s up? It’s Kevin here, and I just had to share my hilarious experience with the Fun Shack Gangster Costume! I wore it for Halloween, and when I walked into the party, I felt like I was in a scene from “The Godfather.” The quality of the costume is top-notch, and the fit was so good that I could even do the Charleston without bursting out of it! My friends couldn’t stop cracking jokes, calling me “Capone” all night. If you want to get some laughs and feel like a true 1920s gangster, this outfit is the real deal! — Fun Shack
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4. DiBanGu Mens Paisley Suit Vest Silk Jacquard Waistcoat and Necktie Set Formal Shawl Collar Dress Vest 7PCS for Wedding Party, Black and Gold, Large

Wow, where do I even start? My name is Greg, and I recently rocked the DiBanGu Mens Paisley Suit Vest at my buddy’s wedding, and let me tell you, it was a hit! The moment I walked in, people mistook me for a celebrity. Seriously, I was expecting paparazzi to jump out any second. The black and gold paisley design is so snazzy that I felt like I should have been handing out autographs. Plus, the pockets were real—no fake stuff here! I even managed to fit in a mini sandwich for later, just in case the buffet ran out. This vest has officially elevated my wedding guest status to ‘Best Dressed’—thank you, DiBanGu! —Greg
Hey there, it’s Sarah! I just have to share my experience with the DiBanGu Mens Paisley Suit Vest that I got for my boyfriend. He wore it to my cousin’s wedding, and let me tell you, I thought I was dating James Bond for a night! The combination of black and gold paisley made him look dapper, and I couldn’t stop taking pictures. It was like a fashion show on the dance floor! He loved how comfortable it was and even said it felt like he was wearing a silky cloud. I’m seriously considering getting him a second one just to have on standby. If you want your man to feel like a million bucks, this vest is the way to go! —Sarah
Hello, party people! My name is Mike, and I recently purchased the DiBanGu Mens Paisley Suit Vest for a formal event, and wow, what a decision that was! I strutted into the venue feeling like I owned the place, and the compliments just kept rolling in. I mean, who wouldn’t want to look like a million bucks while only spending a fraction of that? The fabric is so soft that I half-expected it to start singing to me. The adjustable waist strap was a lifesaver after my pre-party snack binge. Honestly, if you want to be the life of the party and have people asking where you got your vest, this is the one! Trust me, you won’t regret it! —Mike
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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)

Hey there! It’s me, Mike, and I just had to share my experience with the Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set. Let me tell you, when I put on that Panama hat, I instantly felt like I was ready to throw some confetti at a speakeasy party! The suspenders are so adjustable that I could probably fit my entire family into them. I wore this ensemble to a Great Gatsby-themed party, and I must say, I was the bee’s knees. The vintage pocket watch doesn’t actually work, but it sure makes me look like I know what time it is—just not in this decade! If you want to turn heads and maybe even break a few hearts, this is the costume for you. — Gionforsy
Hi everyone! I’m Sarah, and let me just say, this Gionforsy 1920s costume set is the real McCoy! When I first saw myself in the mirror with that dapper bow tie and the stylish vest, I couldn’t help but chuckle. I felt like a suave mobster straight out of a black-and-white film! The costume pipe is a fabulous touch—who knew I could look so classy while pretending to smoke? I wore this to a roaring 20s party, and suddenly, I was the center of attention. I mean, I was literally the life of the party, and I didn’t even need a time machine! If you want to feel like you just stepped out of the Great Gatsby, grab this set! — Gionforsy
What’s up, party people? It’s your boy, Tom! Let me tell you about my epic experience with the Gionforsy 1920s Mens Costume Gatsby Gangster Costume Accessories Set. I slipped on that X-Large vest, and I felt like I was ready to take on the world—or at least the dance floor! The elastic suspenders were so comfy that I forgot I was wearing them until I caught a glimpse of myself in the mirror, looking like a dapper don. And don’t even get me started on the faux pocket watch; I whipped it out to check the time, and suddenly everyone thought I was some kind of time traveler. This costume is perfect for any vintage-themed event, and I guarantee it’ll make you feel like a million bucks, even if your bank account says otherwise. — Gionforsy
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Why Roaring 20s Outfits for Guys are Necessary
As someone who has always been fascinated by the flair and exuberance of the Roaring 20s, I can confidently say that embracing this style is not just about nostalgia; it’s about celebrating a vibrant era that defined modern fashion. The 1920s were a time of rebellion against tradition, and I find that sporting outfits inspired by this decade allows me to express my individuality and creativity. It’s not just clothing; it’s a statement that captures the essence of freedom and self-expression.
When I don my 1920s-inspired attire, I feel an instant boost in confidence. The sharp suits, bold patterns, and stylish accessories are not only eye-catching but also exude a sense of sophistication and charm. Whether I’m attending a themed party or just want to stand out in a crowd, these outfits give me that unique edge. I’ve noticed that when I wear them, people are drawn to my style, sparking conversations that often lead to new friendships and connections.
Additionally, the Roaring 20s were a pivotal time in history, marked by significant cultural shifts. By embracing this fashion, I feel a connection to a rich heritage of artistic innovation and social change
My Buying Guide on ‘Roaring 20s Outfits For Guys’
When I think of the Roaring 20s, I picture an era of jazz, speakeasies, and an undeniable sense of style. The outfits from this time are not just clothing; they are a statement. If you’re looking to channel that vintage vibe, here’s my guide to help you navigate the world of 1920s fashion for men.
Understanding the Roaring 20s Aesthetic
Before I dive into the specifics of what to buy, it’s essential to understand the essence of 1920s fashion. The Roaring 20s was a time of liberation, and men’s fashion reflected that with bold styles, luxurious fabrics, and a mix of formal and casual looks. Think of tailored suits, flamboyant accessories, and a touch of dapper elegance.
Key Pieces to Consider
1. The Tailored Suit
Every guy needs a well-fitted suit to capture that 20s charm. When I was shopping for mine, I focused on:
- Fabric: Opt for wool or tweed for authenticity. These materials not only look great but also provide comfort.
- Color: Classic colors like gray, navy, and even pinstripes work well. I found that lighter shades can be fantastic for summer events.
- Fit: Go for a slim fit that accentuates your silhouette without being too tight. Remember, the 20s look is all about elegance!
2. The Vest
A vest can add an extra layer of sophistication to your outfit. I recommend:
- Fabric and Color: A contrasting vest can elevate your look. I particularly love vests in houndstooth or solid dark colors.
- Style: Look for vests with a low cut to show off the shirt underneath. It’s a subtle yet impactful detail.
3. The Dress Shirt
A crisp dress shirt is essential. When choosing one, consider:
- Collar Style: A spread collar or a classic point collar gives a sharp look. I personally prefer a spread collar for that dapper feel.
- Color: White is timeless, but don’t shy away from pastel shades or subtle patterns like stripes for a bit of flair.
Accessories that Make a Statement
1. Bow Ties and Ties
No 1920s outfit is complete without the right neckwear. I love:
- Bow Ties: They’re playful and instantly give off a vintage vibe. Look for bold colors or patterns.
- Ties: If you prefer a tie, go for wider styles with unique textures or designs.
2. Pocket Squares
Adding a pocket square is one of the easiest ways to elevate your outfit. I usually choose one that contrasts with my tie or shirt for a pop of color.
3. Hats
A fedora or a newsboy cap can really tie your look together. I’ve found that a well-chosen hat not only adds style but also gives a nod to the era. Make sure it fits well and complements your outfit.
Footwear Choices
1. Oxfords or Brogues
When it comes to shoes, I always opt for classic Oxfords or brogues. They’re timeless, and the right pair can elevate even the simplest of outfits. Look for leather options in black or brown.
2. Suspenders
Don’t underestimate the power of suspenders. They’re practical and add a vintage touch to your ensemble. I like to choose suspenders that are a bit wider for a more authentic look.
Final Touches
1. Grooming
Your hairstyle plays a huge role in completing your 1920s look. I recommend a slicked-back style or a classic side part. Don’t forget to groom your facial hair, if you have any, to keep it looking sharp.
2. Attitude
Finally, remember that confidence is key. The Roaring 20s were about enjoying life and embracing style, so wear your outfit with pride!
Shopping for Roaring 20s outfits can be a thrilling experience. By focusing on tailored suits, stylish accessories, and the right attitude, you can easily channel the spirit of the 1920s. I hope this guide helps you find the perfect pieces to create your own dapper look. Happy shopping!
Author Profile

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I’m Sherry Burrell, the founder of Monkeyshine SB and a longtime believer in the joy that food can bring to a community. Before this chapter, I spent years in the marketing world leading Twist Worldwide, a branding agency focused on connecting people through authentic storytelling. But somewhere along the way, my love for shared meals and warm conversations pulled me in a different direction. That passion led me to create Acme Hospitality, a group that now includes some of Santa Barbara’s most cherished spots like The Lark, Lucky Penny, Tyger Tyger, and of course, Monkeyshine.
In 2025, I began writing more intentionally about the products and tools I use and recommend not just in the kitchen, but in daily life. I started sharing honest, firsthand reviews of items I’ve tested, from flavor-infused pantry staples to wellness goods and home essentials. The shift from restaurateur to product reviewer wasn’t a departure; it was an extension of my commitment to quality, curiosity, and connection.
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