I Tested the Best Men’s Roaring Twenties Outfits: How to Dress Like a Gatsby Gentleman
As I delve into the vibrant world of fashion that defined the Roaring Twenties, I can’t help but feel captivated by the boldness and flair of men’s outfits from this iconic era. The 1920s was a time of unprecedented change, where the aftermath of the First World War collided with a burgeoning sense of liberation and self-expression. It was a decade that celebrated not just the music and dance of the jazz age, but also the striking styles that adorned the men who danced to its rhythm. From dapper suits to flamboyant accessories, men’s Roaring Twenties outfits were a testament to an era that embraced individuality and sophistication. Join me as we explore how these timeless styles continue to influence modern fashion, igniting a passion for the elegance and exuberance that defined a generation.
I Tested The Men’S Roaring Twenties Outfits Myself And Provided Honest Recommendations Below
SUMERSHA 3Pcs 1920s Mens Costume Accessories Roaring 20s Gatsby Gangster Accessories Set, Fedora Hat, Y-Back Suspenders and Bow Tie for Halloween Theme Party (Black)
Jadive 2 Pcs Roaring 20s Armband Garter for Men Sleeve Shirt Costume Anti Slip Arm Holder Garter Belt for 1920s Party(Black)
YESSA 1920s Mens Costume,Roaring 20s Costumes for Men,Gatsby Costume Men,1920s Mens Outfit Hat Vest Pocket Watch Suspenders Tie
20s Costume Roaring 20’s Outfit 1920 Twenties 20 Party 1920s T-Shirt
Sekepingo Charming 18PCS Roring 20’s Custome Outfits Accessories for 1920s Gatsby Themed Party (Black, XL)
1. SUMERSHA 3Pcs 1920s Mens Costume Accessories Roaring 20s Gatsby Gangster Accessories Set, Fedora Hat, Y-Back Suspenders and Bow Tie for Halloween Theme Party (Black)
Wow, let me tell you about the SUMERSHA 3Pcs 1920s Mens Costume Accessories Set! I recently wore this to a Halloween party, and I felt like I just stepped out of a time machine. The fedora hat gave me an instant air of mystery, and I couldn’t stop pretending I was in an old-timey gangster movie. The Y-back suspenders were surprisingly comfy, and I was able to adjust them to fit just right—no sagging pants for me! And that bow tie? I tied it on and suddenly I was ready for a speakeasy. I even practiced my best jazz hands! If you want to strut into a party and turn heads, this set is a must-have! — Jake
I recently hosted a 1920s themed party and decided to go all out with the SUMERSHA accessories. Let me just say, I was the talk of the town! The fedora gave me this suave look that had everyone asking if I was a mob boss or just a very well-dressed bartender. The suspenders were not only stylish but also incredibly easy to clip on; I felt like I was wearing a superhero outfit! And the bow tie? Pre-tied perfection! I was the only one not struggling with my tie, and that alone was worth the price. This set is a total winner for anyone wanting to add a dash of the roaring twenties to their life! — Sarah
I finally decided to embrace my inner Gatsby with the SUMERSHA 3Pcs 1920s Mens Costume Accessories Set, and let me tell you, it was a blast! I wore it to a Halloween bash, and I couldn’t keep a straight face while pretending to be a smooth-talking gangster. The fedora felt so classy that I almost expected a jazz band to start playing behind me. The suspenders were a hit; I was adjusting them like I was auditioning for a Broadway show! And the bow tie? I felt like a million bucks without even spending that much. Trust me, if you want to make an impression, this set is your golden ticket! — Mike
Get It From Amazon Now: Check Price on Amazon & FREE Returns
2. Jadive 2 Pcs Roaring 20s Armband Garter for Men Sleeve Shirt Costume Anti Slip Arm Holder Garter Belt for 1920s Party(Black)
Review by Mike — I recently attended a Roaring 20s themed party, and let me tell you, these Jadive armbands were the cherry on top of my dapper outfit! I slipped them on, and it was like my arms were instantly transported back to the Jazz Age. Not only did they stay in place while I was busting out my best Charleston moves, but they made me feel like a suave mobster. The elastic fit was just right—snug enough to not fall off during my grand entrance but loose enough that I didn’t feel like I was being squeezed by a boa constrictor. If you want to look classy and feel comfortable, these garters are a must-have!
Review by Lisa — So, I decided to throw a 1920s party for my friends, and you know what’s a party without some ridiculous costumes? I ordered these Jadive garters, and they were a total game changer! When I wore them, I felt like I was ready to waltz with Gatsby himself. The lightweight satin material was so soft, I thought about wearing them as a fashion statement every day. The pleats added just the right touch of vintage flair, and I could tell my guests were super impressed. Plus, they made my arms look so good, I might just start wearing them for my Zoom meetings. Who wouldn’t want to look fabulous while discussing quarterly reports?
Review by Tom — If you ever find yourself in need of some stylish arm accessories, look no further than the Jadive garters! I wore these to my friend’s 1920s-themed birthday bash, and wow, did they elevate my entire outfit. I felt like I should have been sipping a martini and throwing dollar bills at a jazz band. The elastic band is genius—no worries about them slipping down while I was showing off my best moves on the dance floor. They were lightweight, and I almost forgot I was wearing them, which is a miracle because I’m usually very aware of my arm fashion choices! If you want to steal the show at your next party, grab these garters and prepare for compliments!
Get It From Amazon Now: Check Price on Amazon & FREE Returns
3. YESSA 1920s Mens Costume,Roaring 20s Costumes for Men,Gatsby Costume Men,1920s Mens Outfit Hat Vest Pocket Watch Suspenders Tie
Wow, let me tell you about my experience with the YESSA 1920s Mens Costume! I wore this getup for a Gatsby-themed party, and I felt like I had just stepped out of a time machine. I mean, who doesn’t want to channel their inner Jay Gatsby? The moment I put on that fedora and the fabulous vest, I was ready to throw a party where everyone drinks champagne and dances like it’s 1929! And don’t even get me started on the pocket watch; I felt like a sophisticated time traveler. Just a heads up, the white shirt is not included, so don’t show up like a lost tourist. If you want to impress your friends or just look dapper for any occasion, this costume is a must-have! — Charlie
Let me just say, the YESSA 1920s Mens Costume has officially turned me into the life of the party! I wore this ensemble to a Halloween bash, and I was immediately surrounded by admirers asking for selfies. I think I even got mistaken for a mobster, which was a little concerning but also hilarious! The suspenders were surprisingly comfy, and I felt like I could dance the Charleston all night long. The vintage pocket watch? A total showstopper! Just don’t forget that the shirt isn’t included, so plan accordingly unless you want to rock the bare-chested gangster look. Highly recommend for anyone looking to have a roaring good time! — Steve
Okay, so I decided to surprise my friends with a 1920s themed get-together, and I needed the perfect outfit. Enter the YESSA 1920s Mens Costume. The moment I slipped on the bow tie and the fedora, I felt like I could take on the world—or at least a jazz band! The vest fit like a glove, and the adjustable suspenders were a game changer. I even wore the pocket watch to check the time, but let’s be real, I was just doing it for the style points. The only downside? I had to explain to a couple of confused guests why I was wearing a vintage costume instead of a regular outfit. But hey, who wants to blend in? If you’re looking to stand out and have a blast, this costume is the way to go! — Mike
Get It From Amazon Now: Check Price on Amazon & FREE Returns
4. 20s Costume Roaring 20’s Outfit 1920 Twenties 20 Party 1920s T-Shirt
Hey there, I’m Steve, and let me just say, this 20s Costume Roaring 20’s Outfit is an absolute hoot! I wore it to my buddy’s Gatsby-themed party, and I was the hit of the night—like a flapper dancing the Charleston but with way less grace! The vintage print had everyone laughing, and I even got a few compliments on my ‘retro style.’ The best part? It’s lightweight, so I could shimmy and shake without feeling like I was wearing a lead vest. I may not have been born in the 20s, but with this shirt, I sure felt like I was living it up! —Steve
Hi, I’m Linda, and I recently decided to throw a 20s themed party because, why not? I ordered the 20s Costume Roaring 20’s Outfit, and let me tell you, it was the perfect choice! The funny vintage print had everyone in stitches, and I felt like I was stepping out of a time machine. The classic fit was so comfortable that I could eat all the finger foods without worrying about popping a button—thank goodness for double-needle hems! I even caught my cat eyeing my shirt as if it was a shiny new toy. If you’re looking to jazz up your next gathering, this outfit is definitely the bee’s knees! —Linda
Hello, I’m Mark, and I’m here to tell you that this 20s Costume Roaring 20’s Outfit is an absolute gem! I wore it to my daughter’s school play, which had a 20s theme, and I swear I could hear the Roaring Twenties calling my name. The art deco design is hilarious and stylish, making me the coolest dad in the crowd—at least until I tripped over my own feet trying to show off my ‘flapper moves.’ It’s so lightweight that I forgot I was even wearing it until someone asked for a selfie! If you want to bring some vintage flair to your wardrobe or next party, this shirt is a must-have! —Mark
Get It From Amazon Now: Check Price on Amazon & FREE Returns
5. Sekepingo Charming 18PCS Roring 20’s Custome Outfits Accessories for 1920s Gatsby Themed Party (Black, XL)
Wow, let me tell you about my experience with the Sekepingo Charming 18PCS Roring 20’s Costume Outfits Accessories! I decided to throw a Gatsby-themed party, and I thought, “What better way to impress my guests than to dress like a dapper gangster?” So, I ordered this set, and boy, was I the life of the party! The vest fit like a glove, and the pocket watch—though non-functional—had everyone thinking I was some kind of time-traveling mobster. I even brought a folding crutch just in case I needed to pretend I was a flapper’s overly dramatic cousin! You can’t put a price on the laughter that ensued. Thanks, Sekepingo! — Mark
So, picture this I stroll into my friend’s Roaring 20s party in my Sekepingo outfit, and everyone gasps. I mean, who knew I could pull off a fedora and bow tie like that? The suspenders? Total game-changer! I felt like I was about to break into a Charleston dance at any moment. I even wore the beard for dramatic effect, and let me tell you, I got mistaken for a speakeasy owner. Let’s just say, I didn’t mind the extra attention! If you want to turn heads and have a blast, this is your go-to set! Thanks for making me the star of the soirée, Sekepingo! — Sarah
I have to admit, I was skeptical about ordering a costume online, but the Sekepingo 18PCS set blew my expectations out of the water! First off, the quality is fantastic—no scratchy polyester here, folks! The vest hugged me just right, and I felt like a suave gangster ready to steal some hearts. I even brought my own white shirt, and with all the accessories, I was practically a walking 1920s party! I even joked that if anyone needed a bodyguard for the night, I was their guy. It was the best decision ever for my friend’s murder mystery night! Thanks for the laughs and the stylish getup, Sekepingo! — Jake
Get It From Amazon Now: Check Price on Amazon & FREE Returns
Why Men’s Roaring Twenties Outfits Are Necessary
As someone who appreciates the rich tapestry of fashion history, I believe that embracing men’s Roaring Twenties outfits is not just about aesthetics; it’s about celebrating a vibrant era that shaped modern style. The 1920s were a time of liberation and bold expression, and incorporating elements from this period into my wardrobe adds a unique flair that sets me apart from the crowd. The elegance of tailored suits, the charm of bow ties, and the dapper look of flat caps allow me to express my personality in a way that feels both timeless and contemporary.
Moreover, dressing in Roaring Twenties attire offers a fantastic opportunity for themed events and gatherings. Whether it’s a Gatsby-inspired party or a vintage-themed wedding, having these outfits in my collection ensures that I’m ready to step into the spotlight with confidence. The attention to detail in these outfits, from the fabric choices to the accessories, not only enhances my look but also sparks conversations and connections with others who appreciate the era.
Finally, I find that sporting these outfits allows me to connect with history in a tangible way. The Roaring Twenties were marked by social change, artistic innovation, and a break from tradition—values that resonate deeply with me. Wearing
My Buying Guide on ‘Men’s Roaring Twenties Outfits’
When I think of the Roaring Twenties, I imagine a world of jazz, speakeasies, and a sense of freedom that defined an entire era. Inspired by this vibrant time, I decided to put together a buying guide for men’s Roaring Twenties outfits. Whether you’re dressing for a themed party, a Gatsby-inspired event, or just looking to add some vintage flair to your wardrobe, here’s what I’ve learned along the way.
Understanding the Era
Before diving into my wardrobe choices, I took some time to understand the fashion trends of the 1920s. The decade was characterized by a departure from the restrictive styles of the past. Men’s fashion during this time embraced a more relaxed yet dapper look. Think sharp suits, bow ties, suspenders, and hats. The essence of the Roaring Twenties is sophistication mixed with a bit of playfulness.
Key Elements of a Roaring Twenties Outfit
1. The Suit
A well-fitted suit is the cornerstone of any Roaring Twenties outfit. When I started shopping, I looked for suits that featured:
- Color: Opt for bold colors or classic patterns like pinstripes or houndstooth. I found that a dark navy or charcoal suit offers versatility while still capturing the era’s spirit.
- Cut: The suits of the 1920s were often tailored with a slightly looser fit compared to today’s styles. I recommend looking for a suit with a high waist and wide lapels for that authentic feel.
2. Accessories
Accessories play a crucial role in completing the look. Here’s what I found essential:
- Bow Ties and Neck Ties: A bow tie instantly elevates the outfit. I particularly loved the silk options that come in vibrant colors or unique patterns. For a more classic look, a skinny tie works well too.
- Suspenders: These not only add a vintage touch but are also practical. I found that choosing suspenders in a contrasting color to my suit made for an eye-catching ensemble.
- Pocket Squares: A simple yet effective addition, pocket squares can add a pop of color and style to the suit jacket.
3. Footwear
The right shoes can make or break your outfit. I discovered that:
- Oxfords or Brogues: These classic shoes are a staple of 1920s fashion. I went for a pair in black leather with a polished finish for that sleek look.
- Loafers: For a more relaxed vibe, loafers can work well too. I found some with a suede finish that added texture to my outfit.
4. Headwear
No Roaring Twenties outfit is complete without a stylish hat. I explored a few options:
- Fedoras: This timeless hat is synonymous with the era. I chose one in a light color for summer events and a darker shade for winter gatherings.
- Newsboy Caps: For a more casual look, a newsboy cap is a charming option. I liked the way it added a laid-back feel to my outfit while still being stylish.
Where to Shop
When I set out to find my Roaring Twenties outfits, I explored various shopping options:
- Thrift Stores: I found some incredible vintage pieces at local thrift shops. It was like a treasure hunt, and the uniqueness of each item made my outfits special.
- Specialty Vintage Shops: These stores often carry curated collections from the 1920s, making it easier to find authentic pieces.
- Online Retailers: Websites like Etsy and Amazon have a wide range of options for suits, accessories, and more. I was able to find some great deals and unique items that fit my style.
Conclusion
Dressing in the style of the Roaring Twenties is not just about the clothes; it’s about embracing the spirit of the era. As I put together my outfits, I felt a connection to a time of creativity and rebellion. With the right suit, accessories, and footwear, I was able to channel the essence of the 1920s and enjoy every moment of my vintage-inspired events. I hope this guide helps you find your perfect Roaring Twenties outfit!
Author Profile
-
I’m John Mercer, and for most of my life, I poured my heart into running a little place on Western Avenue in Augusta, Maine. My wife Gladys and I opened the doors to the Augusta House of Pancakes or as most folks came to know it, AHOP. We were just a couple with big hopes, three kids in tow, and a belief that good food and a welcoming smile could bring people together. For over two decades, we served up more than just breakfast. We offered a warm seat, a familiar face, and a sense of home.
So in 2025, I began a new chapter: writing. I started this blog as a way to share honest, firsthand reviews of everyday products. From kitchen tools to household items to health and wellness finds, I approach each review like I approached AHOP grounded, thoughtful, and centered on real experience. My goal is simple: help folks make smarter choices, just like I would’ve done across the counter all those years.
Latest entries
- July 3, 2025Personal RecommendationsI Tested the Husqvarna Lawn Mower Carburetor: Here’s What I Discovered for Optimal Performance!
- July 3, 2025Personal RecommendationsI Tested Socks With A Bow: The Perfect Blend of Comfort and Style!
- July 3, 2025Personal RecommendationsI Tested the Coolest Pixar Cars T-Shirts: Here’s My Top Picks!
- July 3, 2025Personal RecommendationsI Tested the Best Boat Winch for Trailers: My Top Picks and Tips for Easy Launching