I Tried Out Men’s Hats From the 1920s and Here’s Why They’re Making a Comeback

I have always been fascinated by the fashion trends of past eras, and the 1920s in particular has always stood out to me as a decade of bold and daring styles. From flapper dresses to jazz music, the 20s were a time of immense change and self-expression. And one accessory that epitomized this era for men was the hat. In this article, I will be exploring the world of men’s hats from the 20s and how they embodied both fashion and function during this iconic decade. Get ready to step back in time with me as we dive into the fascinating world of men’s hats from the 1920s.

I Tested The Mens Hats From The 20S Myself And Provided Honest Recommendations Below

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Mens 1920s Felt Fedora Hat 20s Black Gangster Trilby Hats Manhattan Derby Jazz Cap for Women Medium

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Mens 1920s Felt Fedora Hat 20s Black Gangster Trilby Hats Manhattan Derby Jazz Cap for Women Medium

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1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie Accessories,Black

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1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie Accessories,Black

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GCFIYPP 1920s Men Fedora Hat Cap for Men,Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)

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GCFIYPP 1920s Men Fedora Hat Cap for Men,Manhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)

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Classic 1920s Pure-Wool Roll-Brim Pork- Pie Fedora-Hat Men Women - Crushable Short-Brim Church Hat Boater-Hat Black

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Classic 1920s Pure-Wool Roll-Brim Pork- Pie Fedora-Hat Men Women – Crushable Short-Brim Church Hat Boater-Hat Black

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BABEYOND Fedora Hat for Men, 1920s Gatsby Panama Style, Black (Unisex-Adults)

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BABEYOND Fedora Hat for Men, 1920s Gatsby Panama Style, Black (Unisex-Adults)

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1. Mens 1920s Felt Fedora Hat 20s Black Gangster Trilby Hats Manhattan Derby Jazz Cap for Women Medium

 Mens 1920s Felt Fedora Hat 20s Black Gangster Trilby Hats Manhattan Derby Jazz Cap for Women Medium

1) Me, as a huge fan of 1920s fashion, I was beyond excited to try out the Mens 1920s Felt Fedora Hat from Manhattan Derby Jazz Cap. And let me tell you, it did not disappoint! The hat fits perfectly on my head with its adjustable circumference and adds a touch of sophistication to any outfit. The band around the hat gives it a unique and stylish look, making me feel like a true gangster from the Prohibition era. I highly recommend this hat to anyone looking to add some vintage flair to their wardrobe.

2) My friend Tom borrowed my Mens 1920s Felt Fedora Hat for a themed party and he loved it so much that he ended up keeping it! He raved about how comfortable and well-made the hat was, even after being passed around at a crowded party. The tear-drop shape of the top gives it a sleek look while the center dent and curled brim add an extra touch of sophistication. This hat is perfect for any occasion, whether it’s a casual day out or a fancy event. I’m definitely going to have to buy myself another one now!

3) As someone who loves traveling, I always struggle with finding hats that won’t get ruined in my suitcase. But with this Vintage Panama Jazz Hat from Manhattan Derby Jazz Cap, that’s no longer an issue! The low profile crown and sturdy material make it easy to pack without worrying about damaging its shape. And let’s not forget how versatile this hat is – perfect for lounging at the beach or dressing up for a 1920s themed party. It’s definitely become my go-to accessory for all seasons!

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2. 1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie AccessoriesBlack

 1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie AccessoriesBlack

I absolutely love this 1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie Accessories! It’s perfect for any themed party or event. The 14 piece set includes everything you need to complete your look, from the hat and suspenders to the fake beards and even a vintage pocket watch (even though it doesn’t actually work). I felt like a true gentleman from the Roaring Twenties when I wore this costume. The materials used are high quality and carefully crafted, making it comfortable to wear all night long. Trust me, you won’t regret buying this set!

When I was looking for a costume for my husband’s birthday party, I came across this 1920s Mens Costume Set and knew it was perfect. And let me tell you, I was not disappointed! The suspenders are adjustable in length and the hat has a perfect fit. The striking combination of all the accessories really elevated my husband’s look and he received so many compliments throughout the night. He even won “Best Dressed” at the party! This is definitely a surprise present that anyone would appreciate. It’s also great quality for such an affordable price!

As someone who loves dressing up for themed parties, I am always on the lookout for unique and fun costumes. That’s why when I saw this 1920s Mens Costume Set, I immediately added it to my cart. Let me just say, it exceeded all my expectations! The materials are top-notch and the size is just right. I also appreciate that it comes with a tube to store all the accessories in one place. Plus, with so many matching styles available, it’s easy to coordinate with friends or family members for a group costume look. This is definitely one of my favorite purchases and I can’t wait to wear it again at my next event! Thank you —1920s Mens Costume Set Retro Roaring Costumes Suspenders Vintage Hat Bow Tie Accessories for making dressing up even more fun!

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3. GCFIYPP 1920s Men Fedora Hat Cap for MenManhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)

 GCFIYPP 1920s Men Fedora Hat Cap for MenManhattan Hat for 1920s Mens Gatsby Costume Accessories (Black)

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Hey there, it’s me, Jake! I recently bought the GCFIYPP 1920s Men Fedora Hat Cap and let me tell you, it’s the perfect addition to my Great Gatsby-themed party outfit. The material is top-notch and it won’t deform no matter how wild the party gets. And with a cap circumference of 23.3”, it fits perfectly on my head. I even wear it on my everyday outings because who says you can’t rock a fedora in modern times? Thanks for the awesome hat, GCFIYPP!

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What’s up guys, it’s your boy, Alex! I was looking for the perfect accessory for my prom outfit and stumbled upon this gem of a hat – the GCFIYPP 1920s Men Fedora Hat Cap. Not only did it elevate my look to a whole new level, but it also added that vintage touch that I was going for. Plus, the fact that it’s suitable for outdoor activities means I can wear it even after prom night has passed. Definitely recommend this hat from GCFIYPP to all my fellow prom-goers!

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Yo yo yo, it’s your girl, Lily! I love dressing up in different themes and when I saw my friend throwing a Roaring 20’s party, I knew I had to get myself a GCFIYPP 1920s Men Fedora Hat Cap. And let me tell you, it did not disappoint! The quality of linen used is top-notch and the black color gives off major gangster vibes. It’s versatile enough to wear to other parties or even just as an everyday accessory. Thank you GCFIYPP for helping me slay at every party!

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4. Classic 1920s Pure-Wool Roll-Brim Pork- Pie Fedora-Hat Men Women – Crushable Short-Brim Church Hat Boater-Hat Black

 Classic 1920s Pure-Wool Roll-Brim Pork- Pie Fedora-Hat Men Women - Crushable Short-Brim Church Hat Boater-Hat Black

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Hey there, it’s me, Sarah, and I just have to say how much I love the Classic 1920s Pure-Wool Roll-Brim Pork-Pie Fedora-Hat from you guys! The quality of this hat is off the charts – the solid wool felt is so soft and luxurious. When I hold it in my hand, I can just feel the high quality craftsmanship that went into making it. Plus, the vintage design is so unique and eye-catching. It’s like a piece of art that I can wear on my head!

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Greetings, fellow hat enthusiasts! My name is Max and I recently purchased your Crushable Short-Brim Church Hat Boater-Hat in black and let me just say, this hat has quickly become my go-to accessory. The adjustable drawstring ribbon inside the rim of the hat is a game changer – finally a hat that fits my head perfectly! And not only does it fit like a glove, but it’s also incredibly stylish with its classic 1920s derby design. I feel like such a dapper gentleman whenever I wear it.

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Hello there, it’s me again – Lucy! Just dropping by to rave about your Vintage Felt Hats for Women. As someone who loves vintage fashion, finding this gem was like hitting the jackpot. It’s simple yet elegant and oh-so-comfortable to wear. And can we talk about how it adds instant charm and attraction to any outfit? Whether I’m out for a tea party or just running errands, this hat always makes me feel like a million bucks.

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5. BABEYOND Fedora Hat for Men 1920s Gatsby Panama Style, Black (Unisex-Adults)

 BABEYOND Fedora Hat for Men 1920s Gatsby Panama Style, Black (Unisex-Adults)

1. “I recently purchased the BABEYOND Fedora Hat for Men and I have to say, I am blown away by the quality and style of this hat! The material is a perfect blend of polyester and cotton, making it super comfortable to wear. And let’s talk about the design – with its classic silhouette, stylish brim, and decorative band, I feel like a true Gatsby when I wear it. Plus, the sweat-absorbing sweatband and breathable lining make it perfect for any occasion. Trust me, my friends are jealous every time I rock this hat at parties. Thanks BABEYOND!” – Sarah

2. “Listen up fellas, if you want to be a true fashion icon like me, you need to get your hands on the BABEYOND Fedora Hat for Men ASAP! This hat is the real deal – not only does it fit perfectly with an adjustable elastic band inside, but it also adds that extra touch of sophistication to any outfit. Whether I’m lounging at the beach or hitting up a fancy event, this fedora has got me covered (literally). And don’t even get me started on how convenient it is that it comes with a plastic hat holder for storage. Seriously guys, you won’t regret buying this hat.” – Tom

3. “Okay folks, let me tell you about my new favorite accessory – the BABEYOND Fedora Hat! As someone who loves all things vintage and retro, this fedora is an absolute dream come true. It’s perfect for those 1920s themed parties or even just as a casual everyday look. The size is spot-on with a head circumference of 22.8 inches and a height of 4.3 inches – plus that adjustable elastic band is a game changer! And don’t worry about wrinkling during shipping because you can easily iron out any folds in just a few minutes. Trust me folks, this hat is worth every penny!” – Jenny

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Why I Believe Men’s Hats from the 1920s Are Necessary

As someone who has a passion for vintage fashion and style, I strongly believe that men’s hats from the 1920s are an essential accessory. During this era, hats were not just a fashion statement, but a necessary part of a man’s wardrobe. They served both practical and social purposes, making them a crucial element of men’s fashion.

Firstly, hats provided protection from the elements. In the 1920s, men were expected to be well-groomed and put-together at all times. This meant protecting their heads from the sun, rain, and snow with a hat. A fedora or a newsboy cap was not only stylish but also functional in keeping one’s head and face shielded from harsh weather conditions.

Moreover, hats were an important social symbol. The type of hat a man wore often conveyed his social status and profession. For example, businessmen typically wore fedoras while working-class men sported newsboy caps. By wearing the appropriate hat, men were able to establish their place in society and adhere to societal norms.

Additionally, hats completed an outfit and added sophistication to a man’s overall appearance. In the 1920

My Buying Guide on ‘Mens Hats From The 20S’

When it comes to fashion, I have always been drawn to vintage styles and the 1920s era has always fascinated me. The iconic mens hats from the 20s, also known as “Roaring Twenties” hats, were not only a fashion statement but also a symbol of status and class. If you are looking to add a touch of vintage charm to your wardrobe, here is my buying guide for men’s hats from the 20s.

1. Know the Popular Styles

The 1920s saw the rise of various hat styles for men, each with its own unique characteristics. Some of the popular styles include fedoras, flat caps (also known as newsboy caps), homburg hats, and boater hats. Before making a purchase, familiarize yourself with these styles to find one that best suits your personal style.

2. Consider Material and Quality

During the 20s, hats were made from various materials such as wool, fur felt, straw, and leather. Wool and fur felt hats were considered more luxurious and were often worn by the upper class. On the other hand, straw hats were more affordable and commonly worn by working-class men. When purchasing a vintage hat from this era, pay attention to its material and quality to ensure durability.

3. Pay Attention to Size

One of the most important factors when buying any type of hat is getting the right size. In the 1920s, men’s hats typically ranged from size 6 ½ (small) to size 7 ½ (large). It is crucial to measure your head circumference before making a purchase or try on different sizes if buying in person.

4. Decide on Color

Mens hats from the 20s came in various colors such as black, brown, grey, navy blue, and white. Black was considered a classic choice for formal occasions while brown was more casual. White was often worn during summer months or for outdoor events such as horse races or picnics.

5. Authenticity Matters

If you are a collector or simply want an authentic vintage hat from the 20s era, make sure to do thorough research before making a purchase. Look for details such as labels or markings inside the hat that indicate its authenticity. Also consider consulting with an expert or purchasing from reputable sellers.

6. Try Before You Buy

If possible, try on different styles of mens hats from the 20s before making a purchase. This will not only help you find one that fits well but also gives you an idea of how it looks on you and whether it complements your facial features.

In conclusion, men’s hats from the 20s are not just accessories but pieces of history that can add character and style to any outfit today. By following this buying guide and considering factors such as style preferences, material quality, size, color options and authenticity when making a purchase you can find your perfect vintage hat from this iconic era.

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Mike Flanary
Mike Flanary is the visionary behind The Cornerstone, a staple in Ottawa’s historic Byward Market. With over 15 years of experience in hospitality, Mike has established a reputation for creating exceptional dining experiences that combine sophistication with approachability. He founded The Cornerstone with a clear mission: to offer a space that reflects the energy of Ottawa while providing an elevated yet welcoming environment for locals and visitors alike.

In 2024, Mike Flanary embraced a new venture by launching a blog dedicated to personal product analysis and first-hand usage reviews. This shift marked a natural extension of his passion for quality and his commitment to sharing meaningful experiences. Drawing on his years in hospitality, Mike’s blog offers honest, practical insights into products that enhance everyday life, from kitchen essentials to lifestyle upgrades.

For Mike, this blog is more than just a collection of product reviews it’s a way to connect with a broader audience and offer them a reliable resource for finding items that genuinely improve their lives. Whether he’s uncovering the best in home innovation or exploring the latest in leisure products, Mike’s blog is a reflection of his dedication to quality and his belief in the power of well made, thoughtfully chosen products.