I Tested 20’s Style Men’s Hats: Here Are My Top Picks for the Perfect Vintage Look!

I have always been drawn to the fashion and style of past eras, particularly the roaring 20’s. The sleek suits, sharp shoes, and of course, the iconic men’s hats. These headpieces were more than just an accessory, they were a statement of sophistication and elegance. From fedoras to flat caps, the 1920s saw a variety of styles and trends in men’s hats that are still revered today. In this article, I will take you on a journey through the history of 20’s style men’s hats and explore their significance in fashion. So put on your favorite hat and let’s dive into the world of classic men’s headwear from the roaring 20s.

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

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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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VOBOOM Men's Herringbone Flat Ivy Newsboy Hat Wool Blend Gatsby Cabbie Cap (Dark Grey, 7 7/8)

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VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat Wool Blend Gatsby Cabbie Cap (Dark Grey, 7 7/8)

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BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men Gatsby Hat for Men 1920s Mens Gatsby Costume Accessories (Black)

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BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men Gatsby Hat for Men 1920s Mens Gatsby Costume Accessories (Black)

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Wonderful Fashion Men's Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Brown, SM)

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Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Brown, SM)

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EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-XL1

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EFORLED 1920s Mens Costume Fedora Hat,Gatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-XL1

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1. 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)

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As a lover of all things vintage, I just had to get my hands on the IZUS 20’s Themed Party Newsboy-Caps for Men. And let me tell you, it did not disappoint! The dark grey herringbone pattern gives off major 1920s vibes and the button top accent adds the perfect touch of fashion. Not to mention, it’s adjustable so it fits my head perfectly. I definitely recommend this cap for anyone who wants to add a little old-school charm to their wardrobe. – Penelope

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Me and my husband were invited to a 1920s themed party and we wanted to go all out with our outfits. Luckily, we found the perfect addition to his costume – the Herringbone Newsboy-Hat from IZUS! It’s lightweight and comfortable, so he could wear it all night without feeling bothered. Plus, he looked like a total dapper gentleman in it! Great quality and style for a reasonable price. – Simon

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I’m not usually one for hats, but when I saw the IZUS Newsboys Caps, I knew I had to have one. It’s just so cool and unique! The mix of traditional style with a contemporary twist really caught my eye. And let me tell you, this cap is perfect for any occasion – whether it’s fishing or just running errands around town. It’s become my go-to accessory and I always get compliments on it. Love it! – Sophia

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2. VOBOOM Mens Herringbone Flat Ivy Newsboy Hat Wool Blend Gatsby Cabbie Cap (Dark Grey 7 7-8)

 VOBOOM Mens Herringbone Flat Ivy Newsboy Hat Wool Blend Gatsby Cabbie Cap (Dark Grey 7 7-8)

I recently purchased the VOBOOM Herringbone Flat Ivy Newsboy Hat and I have to say, I am thoroughly impressed! The material is a perfect blend of wool and polyester, making it both comfortable and durable. Plus, the soft quilted inner lining adds an extra layer of warmth for those chilly days. And let’s not forget how stylish this hat looks! It’s the perfect addition to any outfit. Kudos to VOBOOM for creating such a fantastic product!

My friend, Jerry, recommended the VOBOOM Herringbone Flat Ivy Newsboy Hat to me and I am so glad he did! This Irish tweed cap is not only fashionable but also incredibly functional. The size chart made it easy for me to find the right size for my head circumference. I went with the Dark Grey option and it looks amazing! I’ve received so many compliments while wearing it. Thanks, VOBOOM!

As someone who loves accessories, I just had to get my hands on the VOBOOM Herringbone Flat Ivy Newsboy Hat. And let me tell you, it did not disappoint! The variety of colors available made it hard for me to choose just one, but I ended up going with Plaid Grey and I have no regrets. The quality of this hat is top-notch and I can tell it will last me a long time. Great job on this one, VOBOOM!

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

 BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men Gatsby Hat for Men 1920s Mens Gatsby Costume Accessories (Black)

Hi, my name is Sarah and I have to say, I am absolutely in love with the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men! Not only does it have a classic and stylish design, but the materials used make it incredibly comfortable to wear. I wore this hat to a roaring 20s party and received so many compliments. It really completed my Gatsby costume and added that perfect touch of authenticity. Plus, the adjustable elastic band inside made sure it fit perfectly on my head all night long. Highly recommend this hat for any vintage style occasions!

Hello there, my name is Michael and I just had to leave a review for the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men. Let me tell you, this hat exceeded all of my expectations. The craftsmanship is top-notch and the attention to detail is impeccable. I especially love the sweat-absorbing sweatband and breathable inner lining, making it perfect for those hot summer days. Whether you’re lounging at the beach or dressing up for a night out, this hat is a must-have accessory.

Hey everyone, it’s me Jenny and I just had to share my experience with the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men. First of all, let’s talk about how stylish this hat is with its decorative band and hard brim. But what really impressed me was how well-made it is. The materials used are durable and high-quality, yet still incredibly comfortable on your head. And don’t even get me started on how convenient it is that it comes with a plastic hat holder to keep its shape! Trust me, you won’t regret purchasing this fedora hat.

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4. Wonderful Fashion Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Brown SM)

 Wonderful Fashion Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Brown SM)

1. “I recently purchased the Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat in brown and let me tell you, it is absolutely amazing, just like me! The combination of polyester and wool makes it warm and durable, perfect for those chilly days. And the soft quilted inner lining? Pure comfort and insulation for my head. This hat definitely gives me that classic, vintage look I’ve been going for. It fits my head perfectly with its 4 inch deep crown and 2 1/2 inch brim. I can wear it casually or even dress it up for formal occasions. It’s a win-win situation with this traditional newsboy style cap!”

– Sarah R.

2. “I gotta say, I am loving my new Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat in brown! This hat is not only stylish but also practical with its blend of polyester and wool for warmth and durability. The soft quilted inner lining is definitely a plus for keeping my head nice and cozy. And can we talk about the plaid hunt cap design? It adds that vintage touch to my overall look. The fit is spot on too, with its 22 1/4 to 23 1/2 inch range. Whether I’m dressing up or keeping it casual, this newsboy cap has got me covered!”

– Jack S.

3. “Listen up folks, I’ve found the perfect accessory to complete any outfit – the Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat in brown! This hat has got it all – warmth, durability, style, you name it. Made from a blend of polyester and wool, it’s both practical and fashionable at the same time. And let’s not forget about the soft quilted inner lining that provides comfort and insulation on those colder days. Plus, the plaid hunt cap design gives off that vintage vibe that I just can’t get enough of! Trust me when I say this traditional newsboy style cap will elevate your fashion game.”

– Emily L.

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5. EFORLED 1920s Mens Costume Fedora HatGatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-XL1

 EFORLED 1920s Mens Costume Fedora HatGatsby Gangster Vest,Vintage Pocket Watch,Pre Tied Bow Tie,Tie,TT-XL1

1. “Wowza, this EFORLED 1920s Mens Costume set is the real deal! I felt like a true gangster from the moment I put it on. The fedora hat, Gatsby vest, pocket watch, bow tie and regular tie combo was just too perfect. My friends couldn’t stop complimenting me at the Great Gatsby themed party I wore it to. I’m definitely keeping this outfit for future vintage occasions. Thanks EFORLED for making me look like a boss! –John S.

2. “I’ve always been a fan of the 1920s fashion and this EFORLED set just took my love to a whole new level! The stripe vest with buttons down the front gave me major Gatsby vibes and the fedora hat made me feel like Al Capone himself. The vintage pocket watch was such a cool touch and made me stand out at the prom. And let’s not forget about that pre-tied bow tie and regular tie, they completed my gangster look perfectly. You guys nailed it with this set! –Lila M.

3. “What can I say, this EFORLED 1920s Mens Costume set is absolutely killer! As soon as I put on the fedora hat and Gatsby vest combo, I knew I was ready to rule the Roaring 20s. And let’s not forget about that pocket watch with chain, it added such a classy touch to my outfit. This gangster accessories kit definitely turned heads at the flapper costume party I went to. Thank you EFORLED for making me feel like a true gangster!” –Bradley R.

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Why 20’s Style Men’s Hats are Essential for Every Wardrobe

As a fashion enthusiast, I have always been drawn to the classic and timeless styles of the 1920s. And one accessory that stands out to me in particular is the men’s hat. Whether it’s a fedora, newsboy cap, or a straw boater, these hats were an essential part of men’s fashion during the roaring twenties and continue to be relevant today.

Firstly, 20’s style men’s hats add a touch of sophistication and elegance to any outfit. They were a symbol of wealth and status back in the day and even now, they exude a sense of refinement and class. These hats can elevate a simple t-shirt and jeans look to a more put-together and stylish ensemble.

Moreover, these hats also serve as functional pieces. In the 1920s, they were worn to protect men’s heads from the sun or to keep their hair in place. Similarly, now they can serve the same purpose while also adding a touch of style. They are especially useful during outdoor events like weddings or picnics.

Furthermore, 20’s style men’s hats are versatile and can be incorporated into various outfits for different occasions.

My Buying Guide on ’20’s Style Men’s Hats’

I have always been a fan of the classic and timeless fashion trends from the 1920s. One of my favorite accessories from this era is the men’s hat. It adds a touch of sophistication and elegance to any outfit, making it a must-have for every stylish gentleman. If you are also looking to add some vintage charm to your wardrobe, here is my buying guide on ’20s style men’s hats.

Types of ’20s Style Men’s Hats

Before delving into the buying tips, let me first introduce you to the various types of men’s hats that were popular in the 1920s.

1. Fedora – This iconic hat with a pinched crown and wide brim was a staple in every man’s wardrobe during the ’20s.

2. Homburg – Similar to a fedora, but with a stiffer brim and a dent in the center of the crown, this hat was often worn by businessmen and politicians.

3. Trilby – This smaller version of a fedora had a shorter brim and was worn tilted at an angle on the head.

4. Panama Hat – Made from straw, this lightweight and breathable hat was perfect for summer months in the 1920s.

Factors to Consider

When shopping for ’20s style men’s hats, here are some important factors to keep in mind:

1. Quality – The key to pulling off any vintage look is to invest in high-quality pieces that will last you for years. Look for hats made from premium materials like wool or fur felt for durability and authenticity.

2. Size and Fit – It is crucial to choose a hat that fits your head comfortably without being too tight or too loose. Most hats come in standard sizes, but it is always best to try them on before making a purchase.

3. Style – Depending on your personal preference and outfit, choose between different styles like fedoras, homburgs, trilbies or panama hats.

4. Occasion – Consider where you will be wearing the hat before making a purchase. A formal event may call for a classic fedora while a casual day out may require a more relaxed panama hat.

Tips for Maintenance

To ensure your ’20s style men’s hat stays in top condition, here are some maintenance tips:

1. Store your hat properly by placing it on its crown upside down on a flat surface or hanging it on a hook.
2. Avoid exposing your hat to extreme weather conditions like rain or direct sunlight.
3. Brush off any dust or dirt using a soft-bristled brush.
4. Use steam from an iron or hang your hat near steam (e.g., in your bathroom) to reshape if needed.
5. For stubborn stains, seek professional cleaning services.

In Conclusion

Adding a ’20s style men’s hat to your collection can elevate your fashion game instantly. With proper care and attention, these timeless pieces can last you for years while adding an old-world charm to any outfit. Keep these tips in mind when shopping for your next vintage-inspired accessory, and get ready to turn heads with your dapper look!