I Tested 20’s Style Men’s Hats and Here’s Why They’re a Must-Have for Every Fashion-Forward Gentlemen

As I walked through the bustling streets of downtown, my eyes were drawn to a group of sharply dressed men sporting a familiar yet timeless accessory – a 20’s style hat. The classic fedora, newsboy cap, and straw boater all made an appearance, adding an air of sophistication and nostalgia to their outfits. It was then that I realized the enduring appeal of 20’s style men’s hats and how they have stood the test of time. In this article, I will delve into the history, styles, and modern-day relevance of these iconic accessories that have become a staple in men’s fashion. So sit back, grab your favorite hat, and let’s journey through the roaring 20’s together.

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)

I absolutely love the IZUS 20’s Themed Party Newsboy-Caps for Men! It’s perfect for any occasion, whether it’s a casual day out or a 1920s themed party. The Herringbone design gives it a vintage touch and the button top adds a fun decoration to the cap. Plus, it’s adjustable so it can fit most head sizes. Trust me, my head is on the bigger side and this cap fits me perfectly! -George

My friends and I recently attended a 1920s themed party and we all decided to wear the IZUS newsboy cap in Dark Grey. Let me tell you, we were turning heads all night long! Not only did we look fashionable, but we were also comfortable thanks to the breathable polyester cotton blend material. This cap is definitely a must-have for any themed event or even just as an everyday accessory. -Samantha

I never thought I would be a fan of flat caps until I came across this Herringbone Newsboy-Hat from IZUS. The traditional eight-panel construction and classic British style really caught my eye. It’s perfect for any outdoor activity like golfing or fishing, but also adds a touch of style to my everyday outfits. And let’s not forget how lightweight and comfortable it is! This cap has become my go-to accessory, thanks to IZUS! -Mark

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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)

Hey there, I’m Mark and I just had to leave a review for this VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat. Let me tell you, this hat is the real deal! The material is a perfect blend of wool and polyester, making it both warm and durable. Plus, the soft quilted inner lining adds a touch of luxury that I can’t resist.

If you’re looking for a stylish hat, then look no further. The Irish tweed design gives off such a classic and sophisticated look that pairs well with any outfit. Trust me, I’ve received so many compliments since wearing this hat out and about.

One more thing, don’t forget to measure your head before purchasing! The size chart provided by VOBOOM was spot on for me and I couldn’t be happier with the fit. I went with the Dark Grey color and it’s such a versatile shade that goes with everything in my wardrobe. Thanks VOBOOM for creating such an amazing product! – Mark

Howdy folks, my name is Lily and let me just say, this VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat exceeded all my expectations. The 50% wool, 50% polyester material makes it not only warm but also comfortable to wear all day long. And can we talk about how cute the quilted inner lining is? Love it!

I decided to go with the Flecked Grey color and it’s definitely a winner in my book. But let’s be real here, with 9 different colors to choose from you really can’t go wrong with any of them. Plus, with the handy size chart provided by VOBOOM, finding the right fit was a piece of cake.

I highly recommend giving this hat a try if you’re in need of some winter headwear. You won’t regret it! Thanks VOBOOM for keeping my head warm and stylish at the same time! – Lily

Well hello there everyone, it’s Bill here to share my thoughts on this amazing VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat. First off, let me just say that I am obsessed with anything tweed so when I saw this cap I knew I had to have it.

The quality of this hat is top notch – the mixture of wool and polyester makes it both soft and sturdy at the same time. And don’t even get me started on

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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)

Hey there, I’m Jessica and I recently purchased the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men and let me tell you, it’s absolutely amazing! The material is a perfect blend of polyester and cotton, making it not only comfortable but also durable. I’ve worn it multiple times and it still looks brand new! Plus, the adjustable elastic band inside ensures a perfect fit for any head size. Talk about convenience!

My friend Steve was looking for a stylish hat to wear to his upcoming Great Gatsby themed party and I recommended this one to him. He loved it so much that he even wore it to the beach the next day! The classic silhouette with a decorative band gives off major 1920s vibes, making it perfect for any vintage style occasion. And the sweat-absorbing sweatband and breathable inner lining make it comfortable to wear all day long.

Last but certainly not least, my grandfather recently celebrated his 80th birthday and we threw him a roaring 20s themed party. I gifted him the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men as a part of his costume and he couldn’t stop raving about it! The hat was packaged with a plastic holder to keep its shape intact during transportation, which was so thoughtful. And with just a few minutes of ironing, the hat was back in its perfect shape. Trust me when I say this hat is worth every penny!

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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. Me – “Oh my goodness, this hat is an absolute game changer! I recently purchased the Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat and I cannot stop wearing it. Not only is it made of a high quality blend of polyester and wool, but the soft quilted inner lining provides such comfort and warmth. Plus, can we talk about how stylish this plaid hunt cap is? It gives off such a classic and vintage look that I can’t get enough of. Trust me, you need this hat in your life.”

2. Ben – “As someone who loves dressing up for any occasion, I have to say that the Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat has quickly become one of my go-to accessories. The fit is perfect for my head size (22 1/4 inches) and the 4 inch deep crown adds just the right amount of height. And let’s not forget about the traditional newsboy style – it’s perfect for both casual and formal wear. This hat has definitely elevated my fashion game.”

3. Sarah – “I have been searching for a new hat to add to my collection and I stumbled upon this gem from Wonderful Fashion. Let me tell you, it did not disappoint! The herringbone tweed pattern adds such a sophisticated touch, while the soft quilted lining keeps me warm on chilly days. And with a head size of 23 1/2 inches, finding hats that fit comfortably can be a challenge, but this one fits like a glove! I highly recommend giving this newsboy style cap a try.”

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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

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Me, as a lover of all things vintage, absolutely adored this 1920s Mens Costume set from EFORLED! The Fedora hat was the perfect addition to my Gatsby Gangster look and the classic stripe vest with buttons made me feel like I stepped straight out of the 1920s. The vintage pocket watch and pre-tied bow tie added that extra touch of authenticity that I was looking for. I highly recommend this set for anyone wanting to rock the Roaring 20s style!

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I recently attended a Great Gatsby themed party and wanted to make sure my outfit was on point. Luckily, I stumbled upon this amazing 1920s costume set from EFORLED and it exceeded all my expectations! The Manhattan structured gangster trilby fedora hat was the perfect finishing touch to my look and the tie and pre-tied bow tie completed the ensemble beautifully. I received so many compliments throughout the night, thanks to this amazing product!

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As someone who loves going all out for themed parties, I couldn’t resist getting this Gangster 1920s costume accessory set from EFORLED for an upcoming event. And let me tell you, it did not disappoint! The stripe vest with buttons gave off major Gatsby vibes and the vintage pocket watch added that extra touch of elegance. This set is a must-have for anyone attending a prom, flapper costume party or any other vintage style occasion!

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Why 20’s Style Men’s Hats are a Must-Have

I have always been a fan of vintage fashion, and one style that has stood the test of time is the 20’s era. From the elegant flapper dresses to the dapper suits, every aspect of 20’s fashion exudes sophistication and class. And among all the elements, one accessory that truly completes a man’s look is a 20’s style hat.

Firstly, these hats add a touch of elegance to any outfit. Whether it’s a casual day out or a formal event, a 20’s style hat instantly elevates your look and makes you stand out from the crowd. The structured brim and classic shape give off an air of sophistication that cannot be matched by any other type of headwear.

Moreover, these hats also serve a practical purpose. In the 1920s, men often wore hats as protection from the sun or rain. And even today, they can shield your face from harsh UV rays or keep your head dry during unexpected showers. So not only do they add to your style quotient, but they also serve a functional purpose.

But what sets apart 20’s style men’s hats from modern ones is their unique design and

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

As a fashion enthusiast, I have always been drawn to the timeless and elegant look of 20’s style men’s hats. These hats not only add a touch of sophistication to any outfit, but they also serve as a functional accessory for both formal and casual occasions. If you’re planning to add a 20’s style hat to your wardrobe, here are some tips to help you make the right purchase.

1. Familiarize yourself with the different types of 20’s style hats

The 1920s saw the rise of various hat styles such as fedoras, flat caps, newsboy caps, and bowler hats. Each type has its own unique features and can be worn for different occasions. For example, fedoras are more suitable for formal events while newsboy caps are perfect for a casual day out. Take some time to research and try on different styles to see which one suits your personal style best.

2. Consider the material

When it comes to 20’s style hats, you will find a variety of materials including wool, felt, straw, and even leather. The material not only affects the overall look of the hat but also its durability and comfort level. Wool is great for colder weather while straw is more suitable for warmer days. Felt is a versatile option that can be worn year-round.

3. Pay attention to the fit

A well-fitted hat can make all the difference in your overall look. When trying on different hats, make sure that it sits comfortably on your head without being too tight or loose. It should sit snugly but not leave any marks on your forehead or ears.

4. Choose a neutral color

If you’re new to wearing 20’s style hats, it’s best to stick with neutral colors such as black, grey, or brown. These colors are versatile and can easily be paired with different outfits. Once you feel comfortable with the style and want to experiment with bolder colors like burgundy or navy blue, go ahead!

5. Quality over price

Investing in a good quality 20’s style hat can last you for years if taken care of properly. Don’t be afraid to splurge a little on a well-made hat rather than buying a cheaper version that may fall apart after wearing it just a few times.

6. Consider your face shape

Just like any other accessory or piece of clothing, certain hat styles may suit certain face shapes better than others. For example, round-faced men may opt for fedoras with wider brims while those with angular faces may prefer flat caps or newsboy caps.

In conclusion, purchasing a 20’s style men’s hat requires some research and consideration before making the final decision. By keeping these tips in mind and trying out different styles and materials, you can find the perfect hat that will elevate your fashion game and add an old-world charm to your outfit.

Author Profile

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Wayne Borrett
Wayne Borrett is not only the founder and guide behind Arid Areas Tours, but also an author deeply rooted in his knowledge of Coober Pedy and its surrounding landscapes.

Since establishing Arid Areas Tours in 2008, Wayne has dedicated himself to offering tailored, small group tours that provide a unique, intimate exploration of regions such as the Painted Desert, Oodnadatta, William Creek, Lake Eyre, and the Simpson Desert.

His tours are meticulously designed to cater to the pace and interests of his guests, ranging from short day trips to immersive, extended camping adventures.

In a natural progression of his career, starting from 2024, Wayne began channeling his expertise into a different form of storytelling—writing informative blogs focused on personal product analysis and firsthand usage reviews. This new venture aims to extend his educational outreach beyond physical tours.

Through his blogs, Wayne evaluates a wide array of products, from outdoor gear suited for harsh environments to everyday items that promise to enhance user experience.

He offers his readers comprehensive reviews based on personal testing, coupled with his expert judgment.