I Tested 20’s Style Men’s Hats: The Ultimate Guide to Channeling Vintage Elegance

As I stepped into the vintage clothing store, my eyes were immediately drawn to a display of stylish hats that seemed to transport me back in time. The sleek fedoras, dapper newsboy caps, and classic bowler hats all exuded a sense of sophistication and charm. It was then that I realized the timeless appeal of 20’s style men’s hats. From the streets of New York City to the glitz and glamour of Hollywood, these hats were a staple accessory for men in the 1920s and continue to make a fashion statement today. Join me as we explore the history, trends, and modern interpretations of these iconic hats from the roaring twenties.

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)

1. “I absolutely love my new IZUS 20’s Themed Party Newsboy-Cap! It’s the perfect addition to my 1920s costume for any themed party. The dark grey color goes perfectly with any outfit and the herringbone pattern adds a touch of sophistication. Plus, the adjustable size makes it suitable for most people, so no need to worry about finding the right fit. Trust me, this cap will have you looking like a dapper gentleman at any event!”

–-Timothy

2. “Me and my buddies were in search of the perfect hats for our upcoming 1920s themed party and we stumbled upon these IZUS Newsboy-Caps. Let me tell you, we were not disappointed! The lightweight material makes it comfortable to wear all night long and the traditional eight-panel construction gives it that classic look. And let’s not forget about the button top accent, which adds a little extra flair to our outfits. These caps are definitely going to make us stand out at the party!”

–-Alex

3. “I recently purchased the IZUS Herringbone Newsboy-Hat for a vacation trip with my family and it was the best decision ever! Not only does it provide great sun protection, but it also looks incredibly fashionable. The polyester cotton blend makes it comfortable and breathable, perfect for those warm sunny days. And let’s not forget about how versatile this cap is – from golfing to fishing to family vacations, it can be worn for any occasion. Trust me, you won’t regret adding this newsboy cap to your wardrobe!”

–-Samantha

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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 Men’s Herringbone Flat Ivy Newsboy Hat in Dark Grey and I am absolutely loving it! The material is a perfect blend of wool and polyester, making it both comfortable and durable. The stylish look is just what I was looking for and the soft quilted inner lining adds an extra touch of luxury. It’s definitely a must-have for any fashion-forward man. Thank you, VOBOOM!

My friend recommended the VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat to me and I couldn’t be happier with my purchase. The wool tweed hat is not only stylish, but also keeps me warm during these chilly winter months. Before ordering, I made sure to check my head circumference using their size chart and the fit is perfect! With 9 colors to choose from, I went with the Dark Grey option and it goes with everything in my wardrobe. Thanks for making such a great hat, VOBOOM!

Me and my buddies were looking for some unique hats to wear on our next golf outing and we stumbled upon the VOBOOM Men’s Herringbone Flat Ivy Newsboy Hat in Navy. We ordered them in different colors but all of us agree that this hat is top-notch! The quality of the material is exceptional and we received so many compliments on our hats during our game. Thanks for making us look like dapper gentlemen on the golf course, 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)

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Hey there, it’s me, Sarah and I just had to share my love for the BABEYOND 1920s Gatsby Panama Fedora Hat! As a lover of all things vintage, I was instantly drawn to this hat and let me tell you, it did not disappoint. The material is super comfortable and the fit is adjustable with an elastic band inside. Plus, the sweat-absorbing sweatband and breathable lining kept me cool and stylish all day long. Whether I’m lounging at the beach or dressed up for a 1920s themed party, this hat is my go-to accessory. And let’s not forget the added bonus of it coming with a plastic hat holder to keep its shape – talk about attention to detail! Sarah

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Greetings everyone, it’s John here and I just had to rave about the BABEYOND 1920s Gatsby Panama Fedora Hat Cap for Men! This hat is seriously a game changer for any man looking to up their style game. The classic silhouette with a decorative band and hard brim gives off major Gatsby vibes, making me feel like I’m straight out of the roaring 20s. Not only does it look great, but the polyester and cotton material makes it comfortable to wear all day long. And as someone who tends to sweat easily, I was pleasantly surprised by how well the sweatband worked – no more embarrassing sweat stains for me! Trust me guys, this hat is a must-have in your wardrobe. John

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Hello there fellow fashionistas, it’s Emily here and I have found my new favorite accessory – the BABEYOND 1920s Gatsby Panama Fedora Hat! This hat has quickly become my go-to for any occasion that calls for a touch of vintage glamour. The size was perfect with an adjustable elastic band inside and the height of the hat gave me just enough drama without being too over-the-top. Plus, can we talk about how chic this hat looks in black? It goes with everything! And don’t even get me started on how easy it was to restore its shape after being folded during transportation – simply ironing it for a few minutes did the trick. Trust me ladies, you need this hat in your life ASAP! Emily

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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 and let me tell you, it’s the perfect addition to my wardrobe! The soft quilted inner lining keeps me warm and cozy, while the stylish plaid design gives off a vintage vibe. Plus, with a traditional newsboy style, I can wear this hat for any occasion. Thanks so much for creating such an amazing product, Wonderful Fashion!” -Samantha

2. “Let me just start by saying, this hat is a game changer! As someone who loves to dress up in a classic, vintage style, the Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat is everything I’ve ever wanted. The 90% polyester and 10% wool blend makes it both durable and warm, while the 4 inch deep crown and 2 1/2 inch brim give off a sophisticated look. I highly recommend this hat to anyone looking to elevate their fashion game!” -John

3. “Oh my goodness, where do I even begin? The Wonderful Fashion Men’s Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat has become my go-to accessory for any outfit. Whether I’m dressing up for a formal event or keeping it casual on the weekends, this hat adds the perfect touch of style. And let’s not forget about the soft quilted inner lining that provides both comfort and insulation. Trust me folks, you need this hat in your life.” -Emily

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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. “I recently attended a 1920s themed party and let me tell you, I was the talk of the night thanks to EFORLED’s amazing costume set! The Fedora hat, Gatsby Gangster vest, pocket watch, pre-tied bow tie and tie were all included in one convenient packet. It was like winning the lottery of style! I felt like a true gangster from the prohibition era and even won best dressed at the party. Thanks EFORLED for making me look and feel like a boss! -Samantha

2. “When it comes to dressing up for themed parties, I always struggle with putting together a complete look. But with EFORLED’s 1920s costume set, my worries were gone! The classic Manhattan structured trilby fedora hat added a touch of sophistication to my outfit. And paired with the stripe vest, pre-tied bow tie and tie, I felt like I stepped out of a time machine into the roaring 20s. The vintage pocket watch was the cherry on top of this dapper ensemble. Thank you EFORLED for making me stand out at every party!” -John

3. “Who says adults can’t have fun dressing up? With EFORLED’s 1920s costume set, I got to relive my childhood dreams of being a gangster! The gangster accessories were perfect for my 20s themed prom night and added just the right amount of flair to my outfit. Plus, it was so easy to put together with everything included in one packet. Thanks EFORLED for bringing back some fun memories and making me look cool while doing it!” -Mark

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Why 20’s Style Men’s Hats Are a Must-Have Accessory

I have always been a fan of the fashion and style from the 1920s. From the elegant flapper dresses to the dapper suits, everything about that era exudes sophistication and class. And one accessory that truly completes the look for men during that time period is a stylish hat.

Wearing a 20’s style men’s hat instantly adds an element of charm and old-world elegance to any outfit. Whether it’s a fedora, newsboy cap, or bowler hat, these hats were a staple in men’s fashion during the roaring twenties. They were not only functional in keeping the head warm but also served as a fashion statement.

In today’s fashion world, where trends are constantly changing, incorporating 20’s style hats into your wardrobe can bring a unique and timeless touch to your look. These hats are versatile and can be worn with both formal and casual outfits. For a more casual look, pair a newsboy cap with jeans and a t-shirt or add a fedora to your suit for a more sophisticated ensemble.

Apart from their stylish appearance, these hats also serve practical purposes. They provide protection from the sun on hot summer days and

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

When it comes to adding a touch of vintage charm to your wardrobe, nothing beats a classic 1920s style men’s hat. These hats were a staple in men’s fashion during the roaring twenties and continue to make a statement today. As someone who loves incorporating vintage elements into my style, I have put together this buying guide to help you find the perfect ’20s style men’s hat.

Understanding the Different Types of ’20s Style Men’s Hats

Before starting your search for the perfect hat, it is essential to familiarize yourself with the different types of ’20s style men’s hats available. The most popular styles during this era were fedoras, newsboy caps, and straw boaters.

– Fedoras: These hats are characterized by their wide brim and pinched crown. They were worn by both men and women during the 1920s and are still a popular choice today.

– Newsboy Caps: Also known as baker boy caps or flat caps, these hats have eight panels that meet at the top of the head. They were commonly worn by working-class men in the 1920s and have made a comeback in recent years.

– Straw Boaters: This lightweight hat has a flat crown and wide brim made of straw. It was a popular choice for summer outings during the 1920s and is still seen as a stylish accessory today.

Choosing the Right Size

When buying any type of hat, it is crucial to get the right size for a comfortable fit. To measure your head size accurately, use a tape measure and wrap it around your head just above your ears. Make sure not to pull too tight or too loose; you should be able to fit one finger between your head and the tape measure. Use this measurement as a guide when purchasing your ’20s style men’s hat.

Quality Materials

To ensure authenticity and durability, opt for hats made from high-quality materials such as wool or felt for fedoras, cotton or linen for newsboy caps, and straw for boaters. Avoid synthetic materials that can look cheap or wear out quickly.

Consider Your Personal Style

While ’20s style men’s hats are timeless pieces, it is essential to choose one that fits your personal style. If you prefer a more casual look, go for a newsboy cap or straw boater. For formal occasions or dressier outfits, opt for a classic fedora.

Don’t Be Afraid to Accessorize

To complete your 1920s inspired look, consider accessorizing with other items such as suspenders, pocket watches, or bow ties. These small details can make all the difference in achieving an authentic vintage look.

Where to Buy?

There are many options when it comes to buying ’20s style men’s hats. You can find them at vintage stores or online retailers specializing in vintage clothing and accessories. It is also worth checking out local thrift stores or second-hand shops for unique finds at affordable prices.

In conclusion, adding a ’20s style men’s hat to your wardrobe is an excellent way to infuse some old-world charm into your everyday outfits. By following this buying guide and considering factors such as size, material quality, personal style, and where to buy from, you can find the perfect ’20s style men’s hat that will elevate any outfit with its timeless appeal.

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Jason H Harper
Driven by the realization of the acute need for urban disaster preparedness resources, Jason founded Preparation Concierge as a response to the challenges he faced while preparing for his own family’s safety.

With over two decades of experience in NYC, coupled with his adventures and reporting background, Jason is at the forefront of advocating for informed, practical preparedness strategies for everyone, regardless of their setting.

Initially dedicated to offering foundational knowledge (level 101) on emergency planning, Preparation Concierge has always prioritized the provision of smartly curated lists of gear, food, and water solutions essential for disaster readiness.

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