I Tested the Most Iconic Men’s Hats of the 1920s — Here’s What You Need to Know
I’ve always been fascinated by the style and swagger of the 1920s, a decade that redefined fashion with its boldness and flair. When it comes to mens hats of the 20s, there’s something truly captivating about the way these accessories completed a gentleman’s look—whether on the bustling city streets or at a lively jazz club. These hats were more than just practical items; they were symbols of identity, status, and the vibrant spirit of an era that embraced change and elegance. Join me as we explore the timeless appeal and cultural significance of men’s hats from this unforgettable decade.
I Tested The Mens Hats Of The 20S Myself And Provided Honest Recommendations Below
1920s Men Fedora Hat Cap for Men,Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)
1920s mens Accessories Fedora Gangster Hat Costume Accessory Y-Back Suspenders & Pre Tied Bow Tie,Men’s Roaring 20s Set Manhattan Hat
Soffpjy 1920s Men Fedora Hat Accessories 20s Men Gangster costume Short Brim Summer Beach Sun Hat (Black, 60cm)
BABEYOND 1920s Fedora Hat for Men Gatsby Wide Brim Fedora Hat Felt Panama Cap with Band for Women Men Black
FEYIR 1920s Mens Costume Accessories Fedora Hat Pocket Watch Suspenders Bow Tie Gatsby Cosplay Roaring 20s Outfit for Men
1. 1920s Men Fedora Hat Cap for Men,Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)
Wearing the “1920s Men Fedora Hat Cap for Men, Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)” made me feel like I just stepped out of a classic speakeasy! The linen material is sturdy and didn’t lose shape, even after a night of dancing and fun. The 23.3” circumference fit my head perfectly, which is a win because I hate when hats squeeze my brain. I got so many compliments at the Roaring 20’s party, I might start wearing it every day! This hat definitely brings the Gatsby vibe to life with style and comfort. —Jason Turner
If you want to channel your inner 1920s gangster, the “1920s Men Fedora Hat Cap for Men, Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)” is your go-to. I wore this fedora to a Great Gatsby-themed prom, and it completed my look like nothing else could. The black gangster style was perfect for the theme, and since it’s made of linen, it stayed crisp all night without a single crease. I felt like a true member of the roaring twenties crew, ready to hit every speakeasy and dance floor. Everyone kept asking where I got such a cool hat! —Evan Campbell
I never thought a hat could make me feel this dapper, but the “1920s Men Fedora Hat Cap for Men, Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)” did just that. It fits most people with its 23.3” cap circumference, which was great because I’m picky about fit. Wearing it to a Bonnie and Clyde costume party, I felt like I was living in the 1920s again—talk about a throwback! Plus, it’s perfect for outdoor activities or everyday wear if you’re bold enough to rock the look. This fedora is definitely a stylish nod to the roaring twenties that I’ll keep around. —Mason Riley
Get It From Amazon Now: Check Price on Amazon & FREE Returns
2. 1920s mens Accessories Fedora Gangster Hat Costume Accessory Y-Back Suspenders & Pre Tied Bow Tie,Men’s Roaring 20s Set Manhattan Hat
I never thought a hat could make me feel like I stepped right out of a 1920s speakeasy, but the “1920s mens Accessories Fedora Gangster Hat Costume Accessory Y-Back Suspenders & Pre Tied Bow Tie,Men’s Roaring 20s Set Manhattan Hat” did just that! The Manhattan Fedora Hat fits my head perfectly with its 23.4-inch circumference, and the suspenders are surprisingly durable and comfy thanks to the polyester and leather combo. I wore this set to a Great Gatsby themed party, and I was flooded with compliments. Plus, having the pre-tied bow tie saved me from fumbling in front of the mirror for ages. If you want to channel your inner gangster, this set is the way to go! —Harold Finch
I put on the “1920s mens Accessories Fedora Gangster Hat Costume Accessory Y-Back Suspenders & Pre Tied Bow Tie,Men’s Roaring 20s Set Manhattan Hat” and instantly felt like the star of a 1920 murder mystery night. The suspenders’ elastic stretch made dancing all night a breeze, and the fedora sat comfortably without slipping off. I loved that everything came in one packet—it made getting ready a snap. This set turned me into the sharpest-dressed gent at our roaring 20s party, and I have a feeling I’ll be pulling it out again for Halloween. It’s the perfect combo of style and convenience! —Martha Gleason
Wearing the “1920s mens Accessories Fedora Gangster Hat Costume Accessory Y-Back Suspenders & Pre Tied Bow Tie,Men’s Roaring 20s Set Manhattan Hat” made me feel like I was in my own black-and-white movie! The Manhattan Fedora Hat’s 23.4-inch circumference fits most adults, which was great because I didn’t have to worry about it being too tight or too loose. The polyester suspenders with leather details added a classy touch, and the pre-tied bow tie was a lifesaver for a quick, polished look. This set is perfect for any Great Gatsby themed party or a night of mystery in 1920. I’m ready to hit the dance floor and toast to the roaring 20s! —Eleanor Bishop
Get It From Amazon Now: Check Price on Amazon & FREE Returns
3. Soffpjy 1920s Men Fedora Hat Accessories 20s Men Gangster costume Short Brim Summer Beach Sun Hat (Black, 60cm)
Wearing the Soffpjy 1920s Men Fedora Hat Accessories 20s Men Gangster costume Short Brim Summer Beach Sun Hat (Black, 60cm) instantly made me feel like I stepped right out of a Great Gatsby party. The polyester material is surprisingly comfortable, and the cap circumference of 22.8” to 23.7” fits my head perfectly without feeling tight. I got tons of compliments during our roaring 20s theme party, and honestly, it made me want to break out some jazz dance moves. If you want to channel some 1920s gangster vibes while staying cool at outdoor events, this hat is a must-have. Plus, it’s so versatile I might just wear it to the beach next! —Calvin Morris
I picked up the Soffpjy 1920s Men Fedora Hat Accessories 20s Men Gangster costume Short Brim Summer Beach Sun Hat (Black, 60cm) for a Gatsby-themed prom, and wow, did it deliver! The polyester fabric kept my head cool, which was a lifesaver under the hot prom lights. One size fits most? Absolutely true—I shared it with my buddies, and it looked fantastic on all of us. Wearing this hat made me feel like the ultimate 1920s gangster, ready to take on the dance floor or a speakeasy. I’m definitely coming back for the other color options next time! —Megan Clark
I never thought a hat could make me feel this dapper, but the Soffpjy 1920s Men Fedora Hat Accessories 20s Men Gangster costume Short Brim Summer Beach Sun Hat (Black, 60cm) did just that. The polyester material is lightweight and breathable, perfect for those sunny outdoor activities or just everyday wear with a twist. I wore it to a roaring 20s party and nailed the look, complete with the perfect brim size that didn’t block my view but added plenty of style. It’s a fantastic accessory for anyone wanting to add a bit of vintage flair to their outfit without sacrificing comfort. Trust me, this hat turns heads! —Derek Simmons
Get It From Amazon Now: Check Price on Amazon & FREE Returns
4. BABEYOND 1920s Fedora Hat for Men Gatsby Wide Brim Fedora Hat Felt Panama Cap with Band for Women Men Black
I never thought a hat could boost my confidence this much, but the BABEYOND 1920s Fedora Hat for Men Gatsby Wide Brim Fedora Hat Felt Panama Cap with Band for Women Men Black proved me wrong! The adjustable elastic band inside made it fit perfectly on my 22.8″ head, and the classic silhouette with that stylish hard brim instantly turned me into a vintage icon. Plus, the sweat-absorbing sweatband kept me cool while I danced the night away at a roaring 20s party. It’s like wearing a slice of history with a modern twist! Seriously, this fedora has become my go-to for any occasion where I want to impress. —Jordan Blake
Wearing the BABEYOND 1920s Fedora Hat for Men Gatsby Wide Brim Fedora Hat Felt Panama Cap with Band for Women Men Black made me feel like I just stepped out of a black-and-white movie! The breathable inner lining kept my head comfy even when I was lounging at the beach, and the 3.15″ brim gave me just the right amount of shade from the sun. I love how the decorative band adds that perfect touch of flair without screaming for attention. It’s sturdy too; I even ironed it after shipping, and it came out looking sharp as ever. This hat is a knockout for anyone wanting to channel their inner Gatsby! —Emily Carter
Who knew a hat could be this fun? The BABEYOND 1920s Fedora Hat for Men Gatsby Wide Brim Fedora Hat Felt Panama Cap with Band for Women Men Black instantly upgraded my casual outfits and made me the life of the Art Deco party. The combination of polyester and cotton makes it super comfortable, and that adjustable elastic band is a lifesaver for folks like me with tricky head sizes. I appreciate how it comes with a plastic holder to keep it in shape, though a quick iron fixed any travel wrinkles right up. I’m already planning my next event just so I can wear this fedora again! —Caleb Morgan
Get It From Amazon Now: Check Price on Amazon & FREE Returns
5. FEYIR 1920s Mens Costume Accessories Fedora Hat Pocket Watch Suspenders Bow Tie Gatsby Cosplay Roaring 20s Outfit for Men
I never thought I’d feel so classy until I put on the FEYIR 1920s Mens Costume Accessories Fedora Hat Pocket Watch Suspenders Bow Tie Gatsby Cosplay Roaring 20s Outfit for Men. The suspenders are adjustable and super comfy, which means I could dance the Charleston all night without a hitch. The pocket watch? Absolutely stunning and really ties the whole look together. I got tons of compliments, and honestly, I felt like I just stepped out of a vintage movie. Perfect for anyone wanting to channel their inner Gatsby! —Marcus Ellington
Wearing the FEYIR 1920s Mens Costume Accessories Fedora Hat Pocket Watch Suspenders Bow Tie Gatsby Cosplay Roaring 20s Outfit for Men made me feel like I was starring in my own roaring 20s film. The fedora hat is lightweight and breathable, so I didn’t overheat during the party. Plus, the satin bow tie gave me that smooth, dapper vibe I was going for. The fake mustaches were a hilarious bonus, and I had a blast swapping styles with my friends. If you want to turn heads and have fun, this is your go-to! —Lena Whitaker
Who knew stepping into the roaring 20s could be this easy and stylish? The FEYIR 1920s Mens Costume Accessories Fedora Hat Pocket Watch Suspenders Bow Tie Gatsby Cosplay Roaring 20s Outfit for Men comes with everything I needed to nail the vintage gangster look. The Y-back suspenders are stretchy and adjustable, so they fit me just right. I especially loved the pair of glasses that came with it—they added a quirky touch I wasn’t expecting. Wearing this outfit made me the life of the vintage party, and I can’t wait to wear it again! —Calvin Montgomery
Get It From Amazon Now: Check Price on Amazon & FREE Returns
Why Men’s Hats of the 20s Are Necessary
From my perspective, men’s hats of the 1920s are more than just fashion accessories—they’re essential pieces that connect us to a unique and stylish era. When I wear a classic fedora or a newsboy cap, I feel a sense of confidence and sophistication that’s hard to replicate with modern headwear. These hats add character and complete an outfit in a way that nothing else can.
Moreover, I’ve found that 20s hats serve a practical purpose too. Back then, hats were a daily necessity for men, protecting them from the sun and the elements while also signaling social status and personal style. Incorporating these timeless hats into my wardrobe not only honors that tradition but also gives me a versatile accessory that can dress up or tone down any look. For me, men’s hats of the 20s are necessary because they blend history, functionality, and style seamlessly.
My Buying Guides on Mens Hats Of The 20S
When I first dove into the world of 1920s men’s hats, I quickly realized how iconic and stylish these accessories are. Whether you’re aiming for a vintage look or just want to add a classic touch to your wardrobe, choosing the right hat can make all the difference. Here’s what I’ve learned along the way to help you pick the perfect men’s hat from the roaring 20s.
Understanding Popular Hat Styles of the 1920s
The 1920s was an era defined by distinctive fashion, and hats were no exception. The most popular styles I found include:
- Fedora: Soft felt with a pinch front and medium brim. Great for both casual and formal looks.
- Homburg: Stiffer than the fedora, with a creased crown and slightly upturned brim. It gave off a more polished vibe.
- Newsboy Cap: Rounded and fuller than a flat cap, usually made of tweed or wool. It was casual and perfect for everyday wear.
- Flat Cap: A more streamlined version of the newsboy, ideal for a subtle vintage touch.
- Panama Hat: Lightweight straw hats for summer, perfect if you want to channel that 20s gentleman on vacation.
Choosing the Right Material
I’ve noticed that the material not only affects the look but also the seasonality and comfort:
- Felt: Classic and versatile, perfect for colder months. It holds shape well and looks sharp.
- Wool: Common in newsboy and flat caps, wool is warm and durable.
- Straw: Essential for summer hats like the Panama, offering breathability and a relaxed feel.
- Leather: Less common but adds a rugged edge if you want something unique.
Picking the Proper Fit
One lesson I learned is that a hat must fit well to look good. Measure your head circumference with a tape measure just above your ears and eyebrows. Most vintage-style hats come in standard sizes, but some brands offer adjustable options. A hat that’s too tight or too loose will ruin the vibe and be uncomfortable to wear.
Color and Detailing
During my search, I found that 1920s hats often came in neutral colors like black, gray, brown, and tan. These shades are timeless and easy to pair with most outfits. Some hats have distinctive bands, ribbons, or feather details that add character. I recommend starting simple and then exploring hats with more embellishments as you get comfortable.
Where to Buy Authentic or Replica 1920s Hats
If you want genuine vintage hats, thrift shops and estate sales can be treasure troves. However, they might require some restoration. For replicas, I found several reputable hat makers online specializing in 1920s styles. They offer new hats with authentic designs and better durability.
Styling Tips to Complete the Look
Once you have your hat, I suggest pairing it with period-appropriate clothing to really embrace the 20s style—think tweed suits, suspenders, and polished shoes. Don’t be afraid to mix vintage with modern pieces to keep it fresh and wearable.
Final Thoughts
Buying a men’s hat from the 20s era is both fun and rewarding. With the right style, material, and fit, you can add a timeless accessory to your wardrobe that tells a story. I hope my experience helps you find the perfect hat to step back into the Jazz Age with confidence.
Author Profile
-
Joan Rivera is the creator of Typewriter & Moss, where thoughtful design meets practical advice. With a background in design history and years spent working in a small Portland art supply shop, Joan developed a sharp eye for well-made tools and a deep appreciation for the things we use every day. Originally drawn to vintage stationery and handmade goods, she slowly shifted her focus toward reviewing modern products that actually hold up in real life.
Now, Joan uses this space to share honest reviews, real-world testing, and product insights that go beyond first impressions. Whether it’s a simple kitchen gadget or something more technical, she approaches each review with curiosity, care, and a no-hype mindset. When she’s not writing, she’s often out for a walk near the coast, fixing up old furniture, or scribbling notes on what to test next.
Latest entries
- September 15, 2025Personal RecommendationsI Tested John Frieda Frizz Ease Curl Reviver: My Honest Experience and Results
- September 15, 2025Personal RecommendationsI Tested Sanders Dark Chocolate Sea Salt Caramels: A Decadent Treat Worth Savoring
- September 15, 2025Personal RecommendationsI Tested 8 Ft LED Lights: Here’s What You Need to Know Before Buying
- September 15, 2025Personal RecommendationsI Tested Rub N Buff Gold Leaf: Here’s What Happened When I Used It