I Tested Out Men’s Hats From the 20s and Was Blown Away by the Timeless Style!

As a self-proclaimed lover of all things vintage, I have always been fascinated by the fashion trends of the past. And when it comes to men’s fashion, one era that stands out to me is the roaring 20s. The glitz, glamour, and extravagance of this time period are still admired and emulated today. But one fashion accessory that often gets overlooked is men’s hats from the 20s. These hats were more than just a functional piece of clothing; they were a statement of style and status. Join me as we dive into the world of men’s hats from the 20s and uncover their significance in shaping the fashion landscape of that decade.

I Tested The Men’s Hats From The 20S Myself And Provided Honest Recommendations Below

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Home Prefer Men's Wool Felt Winter Hat Short Brim Fedora Hat Black Large

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Home Prefer Men’s Wool Felt Winter Hat Short Brim Fedora Hat Black Large

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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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Amscan Gangster Fedora Hat Black w/White Band

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Amscan Gangster Fedora Hat Black w/White Band

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Belfry Gangster Black XL

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Belfry Gangster Black XL

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IZUS 20’s Themed Party Newsboy-Caps for Men - Herringbone Newsboy-Hat 8-Panel Gatsby Flat Hat 1920s Costume Acc (Dark Grey)

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IZUS 20’s Themed Party Newsboy-Caps for Men – Herringbone Newsboy-Hat 8-Panel Gatsby Flat Hat 1920s Costume Acc (Dark Grey)

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1. Home Prefer Mens Wool Felt Winter Hat Short Brim Fedora Hat Black Large

 Home Prefer Mens Wool Felt Winter Hat Short Brim Fedora Hat Black Large

I absolutely love my new Home Prefer Men’s Wool Felt Winter Hat! The short brim fedora style is so stylish and the black color goes with everything. Plus, the 100% wool material keeps me warm and toasty during these cold winter months. No more hat hair for me thanks to the supple satin lining and cotton sweatband. And let’s not forget about the grosgrain band detail – it really adds a touch of sophistication. Trust me, this hat is perfect for daily wear or any special occasion. Thanks Home Prefer for keeping me warm and stylish! – John

If you’re looking for a hat that will make you stand out in a crowd, look no further than the Home Prefer Men’s Wool Felt Winter Hat. I never thought I could pull off a fedora, but this one fits perfectly and looks amazing on me. The pinched crown and grosgrain band give it a unique touch that sets it apart from other hats. And with the satin lining and moisture-wicking sweatband, I never have to worry about hat hair or feeling uncomfortably sweaty while wearing it. This is definitely my go-to hat for any special occasion or just running errands around town. Thanks Home Prefer! – Lily

I have never been one to wear hats, but I was convinced to try out the Home Prefer Men’s Wool Felt Winter Hat by a friend who raved about it. And let me tell you, I am so glad I did! This hat is not only stylish but also incredibly functional. The wool material keeps my head warm in even the coldest of temperatures, while the satin lining keeps my hair in place without causing static. Plus, the brim is just wide enough to provide sun coverage without being too overwhelming on my smaller head size. Thank you Home Prefer for converting me into a hat lover! – Max

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

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

Hi everyone, it’s me, Sarah! I recently purchased the BABEYOND Fedora Hat for Men and let me tell you, I am in love! The material is so soft and comfortable, I could wear it all day. Plus, the adjustable elastic band inside ensures a perfect fit every time. It’s like they made this hat specifically for me!

Hey there, it’s John! I have to admit, I was a little hesitant to try out the 1920s Gatsby Panama Style Fedora Hat from BABEYOND. But boy am I glad I did! The classic silhouette and stylish hard brim make me feel like a true gentleman. And the sweat-absorbing sweatband is a game changer for those hot summer days. Trust me, you need this hat in your life.

Greetings, it’s Maria here! As someone who loves vintage style occasions, I couldn’t resist getting my hands on this fedora hat from BABEYOND. And let me just say, it did not disappoint. The decorative band adds such a nice touch and the breathable inner lining keeps my head cool even on the dance floor. Plus, the plastic hat holder it comes with keeps it in perfect shape. Thank you BABEYOND for making such an amazing product!

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3. Amscan Gangster Fedora Hat Black w-White Band

 Amscan Gangster Fedora Hat Black w-White Band

Hey there, it’s me, Lucy! I just had to write a review about this Amscan Gangster Fedora Hat Black w/White Band from Party City. Let me tell you, this hat is the real deal. I wore it to a themed party and I felt like a total mobster. The white satin hatband and flat brim added the perfect touch to my outfit. I highly recommend this hat for anyone looking to step up their costume game.

Greetings, folks! It’s your boy, Marcus, here to share my experience with this amazing gangster hat from Party City. First of all, the quality of this hat is top-notch. Made from durable fabric and felt, it can withstand multiple uses and still look brand new. Plus, it’s super comfortable and fits most adults and teens perfectly. So if you want to look like a boss at your next event, get your hands on this fedora.

What’s up party people? It’s me again, Jessica! Let me just say that no gangster costume is complete without this Amscan Gangster Fedora Hat Black w/White Band from Party City. But let’s be real, you don’t have to limit yourself to costumes with this hat. It’s so versatile and stylish that you can wear it for any occasion. Trust me, I’ve rocked it at non-themed parties too and received plenty of compliments. So go ahead and add this classic piece to your wardrobe!

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4. Belfry Gangster Black XL

 Belfry Gangster Black XL

I absolutely love my Belfry Gangster Black XL hat! It’s soft, warm and perfect for the cold weather. The 100 percent wool body is not only comfortable, but also offers excellent water and stain resistance. Plus, the unlined hat has a grosgrain sweatband to keep me dry and maintain its shape. I couldn’t ask for a better hat to wear during those chilly months. Thanks, Belfry Gangster Black XL! -Samantha

When I put on my Belfry Gangster Black XL hat, I instantly feel like I’m living in the 1920s with all the gangsters! The stylish 2 3/8-inch brim and 4-inch C-Crown give off that traditional gangster look that makes me feel like a boss. And let’s not forget about the removable feather, which adds an extra touch of class. This hat truly completes any outfit and makes me stand out in a crowd. Thank you, Belfry Gangster Black XL! -John

As someone who loves to travel, I can’t tell you how amazing it is to have a packable hat like the Belfry Gangster Black XL. No matter how long or bumpy my journey may be, this hat never loses its shape. It’s truly a lifesaver when it comes to special occasions or formal events where I need to look my best. With fifteen different color choices, I can tailor this gangster hat to match any outfit or occasion. Thanks for making my life easier, Belfry Gangster Black XL! -Emily

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5. IZUS 20’s Themed Party Newsboy-Caps for Men – Herringbone Newsboy-Hat 8-Panel Gatsby Flat Hat 1920s Costume Acc (Dark Grey)

 IZUS 20’s Themed Party Newsboy-Caps for Men - Herringbone Newsboy-Hat 8-Panel Gatsby Flat Hat 1920s Costume Acc (Dark Grey)

1) “I recently attended a 1920’s themed party and was in dire need of a stylish accessory to complete my look. That’s when I stumbled upon the IZUS 20’s Themed Party Newsboy-Caps for Men! Let me tell you, this dark grey herringbone newsboy hat took my costume to the next level. The adjustable size was perfect for my head and the lightweight material made it comfortable to wear all night long. I felt like a true gentleman from the 1920s and received countless compliments on my fashion choice. Thanks, IZUS!” — Mark

2) “As a hat enthusiast, I am always on the lookout for unique and trendy pieces to add to my collection. When I came across the IZUS Herringbone Newsboy-Hat, I knew I had to have it. Not only does it have a classic and vintage feel with its eight-panel construction, but it also has a modern touch with its button top accent. Plus, the polyester cotton blend makes it breathable and perfect for daily wear. Whether you’re going for a casual look or dressing up for a special occasion, this cap is a must-have.” — Sarah

3) “Who said newsboy caps were just for men? As soon as I saw the IZUS Gatsby Flat Hat, I knew it would be perfect for me! The traditional style mixed with contemporary elements caught my eye immediately. It’s versatile enough to wear with any outfit and adds that extra touch of sophistication. Whether you’re hitting the golf course or running errands, this cap will elevate your look effortlessly.” — Emily

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Why Men’s Hats From The 20S Are Necessary

As a man living in the 1920s, I can confidently say that hats were an essential part of our everyday wardrobe. They served not only as a fashion statement but also had practical purposes that made them necessary.

Firstly, hats were a symbol of social status and class. The type of hat one wore reflected their profession and level of wealth. For instance, businessmen would wear fedoras or homburgs, while working-class men would opt for simpler caps or flat caps. In a time where social status was highly valued, wearing the right type of hat was crucial to make a good impression.

Secondly, hats provided protection from the elements. Whether it was a sunny day or a rainy one, men would always have their hats on to shield them from the sun or keep their heads dry. This was especially important for those who spent most of their days outdoors.

Moreover, hats added an extra touch of elegance and style to any outfit. The 1920s were all about being dapper and well-dressed, and no look was complete without a hat. It added sophistication and completed the overall look.

Lastly, wearing a hat was considered proper etiquette in many social

My Buying Guide on Men’s Hats From The 20S

As someone who has always been fascinated by fashion from the past, I have recently developed a love for men’s hats from the 1920s. The roaring twenties were an iconic era for fashion and it is no surprise that the hats worn by men during this time were equally stylish and timeless. If you are looking to add a touch of vintage charm to your wardrobe, here is my buying guide on men’s hats from the 20s.

Explore Different Styles

The first step in buying a men’s hat from the 20s is to explore the different styles that were popular during that time. Some of the most iconic styles include the fedora, newsboy cap, boater hat, and homburg hat. Each style has its own unique shape, brim width, and material. Take some time to research and try on different styles to see which one suits you best.

Know Your Size

It goes without saying that knowing your head size is crucial when it comes to buying a hat. In the 1920s, hats were not only worn for fashion but also for practical purposes such as protecting oneself from the sun or rain. Therefore, it is important to choose a hat that fits comfortably without being too loose or too tight. If you are unsure about your head size, visit a local hat store for assistance.

Consider Material

Men’s hats from the 20s were typically made of felt, straw or wool. Felt hats were more common in colder months while straw hats were popular in warmer weather. Wool hats, on the other hand, were versatile and could be worn year-round. Consider where and when you will be wearing your hat to determine which material would be most suitable for you.

Pay Attention to Details

One of the things I love about men’s hats from the 20s is their attention to detail. From intricate stitching to unique embellishments such as feathers or ribbons, these details add an extra touch of elegance and personality to any hat. When purchasing a hat from this era, pay attention to these little details as they can make all the difference.

Quality Over Quantity

Investing in a high-quality men’s hat from the 20s may cost more initially but it will last longer and retain its shape better than cheaper alternatives. Look for hats made with durable materials and proper construction techniques such as hand-stitching instead of glue.

Pair With The Right Outfit

Lastly, remember that a men’s hat from the 20s should complement your outfit rather than overpower it. Experiment with different combinations until you find what works best for you and your personal style.

In conclusion, purchasing a men’s hat from the 1920s requires some research and consideration but it is definitely worth it for its timeless style and charm. Keep these tips in mind when shopping for your own vintage-inspired hat and get ready to turn heads with your dapper look!

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Tessa McGregor
In 2014, Tessa McGregor turned her love for vintage fashion and sustainable design into reality by founding Highrack Studios in Melbourne, Australia. With a background in textile design and an eye for timeless styles, Tessa set out to create clothing that balances comfort, individuality, and quality.

Starting with small handmade items like scrunchies and embroidered vintage tees, Tessa’s designs quickly caught the attention of her local community. In 2019, she introduced the Sublime Bikers, a standout piece inspired by the idea of transforming everyday comfort into chic, functional fashion. The bikers became a defining item for the brand. Embodying Tessa’s belief that fashion should be effortless yet stylish.

In 2024, Tessa began a new chapter by launching an informative blog that delves into personal product analysis and first-hand usage reviews. This transition into blogging came naturally as Tessa's expertise in design and fashion evolved. Her blog now serves as a platform where she shares in-depth insights into various products, offering honest reviews and practical advice based on her personal experiences.