Gambler Hat

Shelby Lane
18 min readMar 22, 2024



Welcome to our roundup of the top Gambler Hat options on the market today! In this article, we’ve curated a selection of hats that are perfect for the gambler in you. Whether you’re heading to the casino or just looking to add a touch of luck to your wardrobe, we’ve got you covered. Get ready to explore the best hats for the gambler in you!

The Top 16 Best Gambler Hat

  1. Faux Felt Gambler Cowboy Hat — Upgrade your Western outfit with this stylish, gambler-inspired faux felt cowboy hat available in two sizes (Small and Large), featuring a 4" crown and 3 1/2" brim, elastic head fit, and a sleek black finish.
  2. Stylish Crushable Wool Gambler Hat from Stetson — Experience unbeatable style and durability with the Stetson Kelso Crushable Wool Gambler Hat, a premium outdoor accessory crafted in the USA with 100% wool felt, faux leather accents, and a dri-lex sweatband for ultimate comfort.
  3. Crushable Twister Gambler Black Hat — Experience the perfect blend of style and durability with the M&F Western Products Gambler Crushable Hat, featuring an adjustable closure, hand wash instructions, and a matching hat band.
  4. Stylish and Portable Wool Felt Gambler Hat — Unpack the style and comfort with Jaxon Hats Crossfire Wool Felt Gambler Hat in L Black, featuring a faux leather hat band with silver metallic concho accents for an exclusive touch.
  5. Classic Gambler Straw Hat — Vintage Inspired Headwear — Experience the classic charm of a gambler’s hat with the comfortable fit and sophisticated design of our 100% natural straw and elastic sweat band gambler hat in navy band.
  6. Stylish Western Gambler Hat with Telescope Crown — Experience the classic western charm with the Jaxon Wool Gambler Hat, featuring a telescope crown, grosgrain ribbon hatband, and a 100% wool construction, perfect for any adventure!
  7. Elegant Black Wool Silverado Men’s Gambler Hat — The Silverado Men’s Gambler Black Wool hat offers a perfect blend of rustic style and comfort, with its quality wool construction, stylish silver accents, and charming 3 1/8 inch brim.
  8. Women’s Woven Paper Gambler Hat in Natural by San Diego Hat Co. — Stay fashionable at the table with the San Diego Hat Company Women’s Woven Paper Gambler Hat — a stunning combination of woven paper and studded leather band, perfect for women seeking a one-of-a-kind hat accessory.
  9. Sea Grass Straw Gambler Hat for Sun Protection — Keep cool in the sun with this stylish and comfortable Gambler Hat, featuring a wide brim, elastic sweat band and UPF 50+ sun protection.
  10. Ventilated Gambler Hat for Ultimate Comfort — Experience ultimate breathability and sun protection with Jaxon Hats’ Pebble Beach Seagrass Gambler Hat, featuring a 3-pleat cotton hatband, elasticized terrycloth sweatband, and stylish cotton underbrim and crown tip.
  11. 3X Wool Gambler Western Hat for Men — Experience premium craftsmanship with the Cody James Men’s 3X Wool Gambler Western Hat, featuring a 3 1/2" brim, leatherette embellishments, and a bull rider crease, all handcrafted in the USA.
  12. Versatile Gambler Hat for Outdoor Adventures — Experience the ultimate outdoor adventure in style with the Men’s Palm Braid Gambler Hat — perfect for fishing, camping, and more, available in various colors and sizes.
  13. Gambler Hat with Telescope Crown — Ginger — The Gigi PIP Ginger Gambler hat is a versatile and stylish classic, featuring a 100% Australian wool crown and upturned brim that complements various hairstyles.
  14. Richardson’s Stylish Gambler Straw Hat — Experience timeless style and sun protection with the Richardson 824 Classic Gambler Hat, a versatile straw hat designed for comfort and convenience.
  15. Protective and Elegant Gambler Hat for Ladies — Experience protected style and comfort with the Scala Leather Band Gambler Hat for Ladies, featuring a UPF 50+ sun protection rating, adjustable interior sweatband, and chin cord for windy days.
  16. Stylish Stetson Shantung Straw Gambler Hat, Made in the USA — Experience timeless elegance with the Stetson Colonel Shantung Straw Gambler Hat, a handcrafted masterpiece made of premium shantung straw and genuine cowhide leather, perfectly fitting true to size while showcasing classic style and comfort.


Faux Felt Gambler Cowboy Hat


As a cowboy enthusiast, I’ve been eyeing this Western Faux Felt Gambler Cowboy Hat for quite some time. When it finally arrived, I was ecstatic to try it out. The hat, available in both smaller and larger sizes, has an elastic band that fits well, accommodating head sizes 55cm to 57cm for the small size and 59cm to 61cm for the large.

The hat itself has a 4-inch crown and a 3.5-inch brim, which gives it a classic look that’s perfect for cosplay or just wearing on a sunny day. The faux felt construction and silver band give it a genuine Western feel, especially when paired with a matching outfit.

One downside, however, was the sizing. While the elastic band made it comfortable to wear, the hat felt a bit too tight around the crown. And despite the availability of two sizes, I found that the sizes didn’t match up exactly to my head size, resulting in a slightly uncomfortable fit.

Despite the sizing issue, I was overall pleased with this hat. It added a nice touch to my cowboy ensemble, and the faux felt material made it durable enough to withstand the elements. With its classic design and comfortable fit, this Western Faux Felt Gambler Cowboy Hat is a worthy addition to any cowboy enthusiast’s collection.

Stylish Crushable Wool Gambler Hat from Stetson


I stumbled upon the Kelso Crushable Wool Gambler Hat by Stetson, and it quickly made its way into my daily rotation. The softness of the wool felt caught me off guard — it’s not only durable in various weather scenarios, but also surprisingly comfortable.

One of my favorite features has to be the hatband, with a touch of faux leather and a striking feather overlay. It gives the hat a unique and refined look that sets it apart from the usual. Though, it might be a little loud for some casual settings, like grocery shopping or playing ball.

But perhaps what blew me away the most was the sweatband, engineered with dri-lex — a moisture-wicking material that dries incredibly fast, ensuring your head stays cool and dry under even the toughest conditions. It made my outdoor adventures more enjoyable and hassle-free.

My only critique? Perhaps the hat could use a bit more variety in the color options. It’s definitely a standout, but I’d like to see more choices for folks who may not be as bold as I am with my fashion choices. Regardless, this hat is a durable, stylish, and comfortable choice for any adventurer or city stroller. And with it being made in the USA, it’s an added bonus for those who appreciate local craftsmanship.

Crushable Twister Gambler Black Hat


This Twister Gambler Crushable Hat from M & F Western Products offers western style enthusiasts the perfect blend of fashion and function. The large black hat features a Twister pin and is handcrafted from premium materials. One of the standout features of this hat is its crushable wool design, which allows it to be easily flattened for storage or transport without losing its shape. The adjustable closure ensures a comfortable fit for any head size, while the hand wash-only care instructions help keep this stylish accessory looking its best.

Though not every user has had a perfect experience with this hat, the majority of reviews praise its look and fit. Some users have appreciated the versatility of the Gambler Hat, while others have been impressed by the value and service they received. Overall, the Twister Gambler Crushable Hat is a stylish choice for those seeking a western-inspired hat with a touch of sophistication.

Stylish and Portable Wool Felt Gambler Hat


Being a gambler at heart, I wanted to try something stylish that would last me throughout the year. That’s when I stumbled upon the Jaxon Hats Crossfire Wool Felt Gambler Hat. The first time I wore this hat, I felt like I was walking into the Wild West. The rich black hue, combined with the silver metallic concho accents, added a touch of authenticity to my look.

What really stands out is the hat’s construction — it’s made of 100% wool, making it packable and lightweight. I took it with me on my road trips, and it never felt heavy or bulky. The faux leather hat band, adorned with tassels, looked elegant and complemented the overall design.

However, the simple unlined interior and cotton twill sweatband didn’t seem very luxurious. It was comfortable, but it lacked the refined touch that I was hoping for. The telescope crown and upturned brim were functional, but they weren’t as striking as the other features.

Overall, my experience with the Jaxon Hats Crossfire Wool Felt Gambler Hat has been positive. It’s stylish, comfortable, and versatile, making it perfect for casual outings and themed events. But, it could use some refinement in terms of its interior lining to give it a more upscale feel.

Classic Gambler Straw Hat — Vintage Inspired Headwear


Recently, I tried out the Mg Gambler Straw Hat in navy band. Made with 100% natural straw, this hat offers a comfortable and classic look with a modern twist. The roomy crown and inner elastic band ensure a perfect fit, while the wide brim and dark green hat band provide ample sun protection.

The gambler-inspired design adds an element of mystery and style to any outfit. However, I wish it had come in a wider range of colors and sizes to accommodate different preferences and head shapes. Overall, it’s a great choice for those seeking a stylish and functional gambler hat with a vintage touch.

Stylish Western Gambler Hat with Telescope Crown


I recently had the chance to try out the Jaxon Hats Crushable Wool Felt Gambler Hat in size M Black. What caught my eye about this hat was its western style design with a funky twist. Dressed in 100% wool, it’s a sturdy and stylish choice for anyone wanting to make a statement.

The underwelt brim is approximately 3 3/8 inches, which provides a nice balance of protection from the sun and a distinctive look. On the other hand, the telescope crown measures around 3 5/8 inches, adding a playful touch to the overall design. One feature that stood out was the cotton sweatband inside, which made it incredibly comfortable to wear even during long gaming sessions.

While I appreciate the unique design, there are a couple of drawbacks. Firstly, the hat is unlined, which might not be ideal for those chilly nights under the casino lights. Secondly, the Jaxon side pin, a small detail, might be overlooked by some customers who prefer a more simple design.

Overall, the Jaxon Wool Gambler Hat is a stylish and comfortable choice for those looking to bring a touch of western flair to their gaming experience. With its durable wool felt body, grosgrain ribbon hatband, and cotton sweatband, it’s a perfect addition to any gambler’s outfit.

Elegant Black Wool Silverado Men’s Gambler Hat


The Silverado Men’s Gambler has been a reliable addition to my outdoor adventures. For those of us who enjoy a little risk, this cowboy hat is a perfect blend of style and comfort. Made from durable wool, it can take a beating without losing its shape, a testament to its crushable properties.

The 3 1/8 inch brim provides ample shade, even on the sunniest days. I must say, I’ve been quite satisfied with the quality of wool felt construction and the intricate silver-tone conchos and nail heads on the hat band.

However, the hat band could have been designed with a bit more thought — I noticed it only appearing on one side, causing an imbalance in overall appearance. Despite this minor flaw, it has become a trusty companion on my wild rides, ready to stand by my side in the roughest conditions.

Women’s Woven Paper Gambler Hat in Natural by San Diego Hat Co.


For the past month, I’ve been wearing the beautiful San Diego Hat Company Women’s Woven Paper Gambler Hat. I’ve received many compliments on its unique design!

The natural color of the hat is a perfect match for my outfits. It feels comfortable and lightweight thanks to the 100% paper material, which has a surprisingly natural and pleasant texture to it. However, I also noticed a slight downside: the hat seems to require a bit more care than I expected, as it tends to get wrinkled quite easily.

When I put it on, the 3.75" brim size provides an ideal amount of shading from the sun. The one-size fits all, with a circumference of 57cm, makes it incredibly convenient for me to wear without any adjustments.

The studded leather band adds an eye-catching touch of elegance to the hat. Although it’s not the sturdiest material, it does provide a stylish appeal. But beware, the hat is not water-resistant, so it may not be the best choice for outdoor activities lasting a long time.

Overall, I believe this San Diego Hat Company Women’s Woven Paper Gambler Hat is a great choice for those who want a stylish and unique hat for their outfits. However, it may require a bit more care to keep it looking its best.

Sea Grass Straw Gambler Hat for Sun Protection


The Outdoor Sea Grass Gambler Hat became my go-to accessory for outdoor adventures this past summer. Made from 100% sea grass straw, this hat not only looked stylish but provided excellent sun protection.

The large brim shielded me from harsh rays, and the sweat band kept me cool even during the hottest days. With its unisex design and one-size-fits-all approach, it was perfect for sharing with friends during our group outings.

The sea grass straw material was both comfortable and breathable, and the adjustable fit ensured a snug and secure hold. However, I wish it came in more vibrant colors to make it stand out even more. Overall, this Gambler hat proved to be a reliable and practical addition to my summer wardrobe, and I can’t wait to use it again next season.

Ventilated Gambler Hat for Ultimate Comfort


I recently gave the Jaxon & James Pebble Beach Seagrass Straw Gambler Hat a try, and let me tell you, it’s become my go-to accessory for those hot summer days. The 3-pleat cotton hatband adds a classic style to the hat, and the elasticized terrycloth sweatband is a lifesaver for maintaining a comfortable fit. The 100% seagrass construction provides maximum breathability, and the cotton underbrim and crown tip keep the sun at bay.

One of the highlights of this Gambler Hat is how lightweight it is, making it a perfect companion for a day out in the sun. However, it’s not without its flaw; the seagrass can become a bit flimsy over time, but all things considered, I’m happy with my purchase. If you’re in the market for a stylish yet functional sun hat, give the Pebble Beach Seagrass Straw Gambler Hat a chance — you won’t regret it! .

3X Wool Gambler Western Hat for Men


Imagine strutting down the street in a hat that exudes both style and comfort. That’s exactly what you get with the Cody James Men’s 3X Wool Gambler Western Hat.

With its sleek Gambler crown and 3 1/2" brim, this hat is perfect for those looking to make a statement. The 3X wool blend construction ensures durability and comfort, making it a must-have accessory for any outdoor adventure.

The elastic sweatband keeps you cool even in the scorching heat, while the leatherette outside band with embellishments adds a touch of elegance. Available in sizes 6 1/4" — 8" and handcrafted right here in the USA, this hat is a true testament to American craftsmanship. The bull rider crease adds a unique touch, and knowing it’s made in the USA gives you an extra sense of pride.

So why wait? . Step up your style game with the Cody James Men’s 3X Wool Gambler Western Hat today! .

Versatile Gambler Hat for Outdoor Adventures


The Men’s Palm Braid Gambler Hat is a versatile and stylish accessory for outdoor enthusiasts. The natural fiber construction not only feels comfortable on our head but also provides a sturdy and durable build. With three different sizes available, including M, L, and XL, it caters to a wide range of men’s head sizes.

One feature we particularly appreciate is the inner elastic sweatband, which keeps our head dry and sweat-free, even during long outdoor activities. The hat’s deep 3.5-inch crown and 3.5-inch wide brim provide ample shade, while the slight upturn in the side brim adds a fashionable touch.

The hat also boasts three small air vents on each side, which helps to regulate temperature and keep us cool in the hot summer months. The black band around the crown and the tear-drop shaped top crown add an elegant look to the hat.

Despite its many advantages, the Gambler Hat comes with a few minor drawbacks. It’s only meant to be hand washed, which might be inconvenient for some users. Additionally, this hat might not be the best choice for cold or rainy weather, as it lacks a waterproof feature. However, for warm and sunny days, we find this hat to be a perfect companion for our outdoor adventures.

Gambler Hat with Telescope Crown — Ginger


The Gigi PIP Ginger Gambler Hat, a fresh take on the classic gambler style, is a delightful addition to any wardrobe. With an indented oval crown and an upright brim, this hat is perfect for styling with any hairdo, offering both versatility and comfort. Crafted from 100% Australian wool, this Ginger Gambler Hat is a must-have for those seeking a stylish, adjustable hat.

I recently had the chance to try this hat myself, and I was impressed by its adaptability. The telescope crown allowed for easy customization with removable bands, making it easy to switch up the look. The hat fits snugly on my head and feels comfortable, even when tilted back. I particularly enjoyed the fact that it wasn’t too heavy to wear, making it a great choice for various occasions.

However, there were a couple of minor flaws that I noticed. While the hat is made from high-quality material, the shipping process left a slight scratch on the surface. Additionally, as with any accessory, it requires proper care, and I suggest cleaning the hat and storing it flat to maintain its shape.

Overall, the Gigi PIP Ginger Gambler Hat is an excellent choice for those looking for a versatile, stylish, and comfortable accessory. The combination of its quality craftsmanship and adaptability makes it a standout among other hats in the market. Despite the minor issues, I would definitely recommend giving this hat a try, especially if you’re looking for a fresh take on the classic gambler style.

Richardson’s Stylish Gambler Straw Hat


As a fan of stylish hats, I couldn’t resist trying the Richardson Classic Gambler Hat. This bad boy perfectly complements my laid-back summer outfit, and it’s a great conversation starter.

The 3-inch brim is just the right size to shield my eyes from the sun while the breathable 100% Toyo straw keeps me cool during warmer days. However, one downside is that the design might be a bit too bold for some casual occasions, but overall, it’s a fantastic addition to my hat collection.

Protective and Elegant Gambler Hat for Ladies


The Scala Leather Band Gambler Hat for Ladies is an essential addition to any summer wardrobe. With a UPF 50+ sun protection rating, this stylish hat keeps you shielded from harmful rays while you’re out enjoying the great outdoors. Its 4-inch-wide brim provides ample coverage, yet it manages to maintain a slimline profile that’s both fashionable and functional.

One of the standout features is the adjustable interior sweatband, ensuring your comfort in even the stickiest of situations. The hat also comes equipped with an adjustable chin cord, making it a reliable companion for those windy days when you need an extra layer of security. Crafted from a blend of 80% paper and 20% polyester, it’s durable, lightweight, and comfortable to wear.

While the one-size-fits-most claim holds true for most users, some may find it a bit snug around the face. Overall, the Scala Leather Band Gambler Hat for Ladies offers excellent sun protection and a touch of elegance that makes it perfect for any sunny adventure.

Stylish Stetson Shantung Straw Gambler Hat, Made in the USA


Recently, I was on the hunt for a new Gambler hat, and I came across the Colonel Shantung Straw Gambler Hat by Stetson. As someone who enjoys a stylish and practical piece of headwear, I was intrigued by the product’s features, including the 4" Gambler Crown and 3" curled brim. I was also excited that it was made in the USA using premium shantung straw.

Upon receiving my hat, I was immediately impressed by its craftsmanship and quality. The straw had a firm and rigid feel, while the curled brim and grosgrain ribbon hat band added an elegant touch. The genuine cowhide leather sweatband and Stetson crown tip detail made it a truly handsome piece. The only downside was the size, which seemed to be slightly larger than I had anticipated.

Overall, the Colonel Shantung Straw Gambler Hat by Stetson is a well-crafted and versatile accessory that would make an excellent addition to any Gambler’s wardrobe. Just be mindful of the sizing and ensure you order the perfect fit.

Buyer’s Guide


Are you looking to purchase a Gambler Hat but unsure of what to consider? This buyer’s guide will help you navigate the various features and aspects of Gambler Hats to make an informed decision.

Important Features

  1. Material: Gambler Hats are usually made from durable materials, such as felt, straw, or canvas. Felt is the most common material, known for its durability and water resistance. Straw and canvas hats offer breathability and comfort in warmer weather.
  2. Design: The design of a Gambler Hat can vary, but most feature a wide-brimmed shape that provides sun protection. Some hats may also have a visor or a chinstrap for added style and functionality.
  3. Fit: Ensure the hat fits well and sits comfortably on your head. Measure the circumference of your head and compare it to the sizing chart provided by the manufacturer.


  1. Occasion: Determine the purpose of the hat. If you’re planning to wear it at a formal event, consider a more understated design. For casual outings, a more flamboyant and eye-catching design may be appropriate.
  2. Climate: The climate of your region can influence your choice of hat. In cold weather, a felt hat may be the best option, while straw or canvas hats are ideal for warmer climates.

General Advice

  1. Inspect the quality of the hat: Check for any tears, rips, or loose threads, as these can affect the hat’s durability.
  2. Consider the brand: Research the brand’s reputation for quality and customer service before making a purchase.
  3. Read customer reviews: Reviews can provide valuable insight into the hat’s performance, comfort, and overall satisfaction.
  4. Care for your hat: Proper care and storage will prolong the lifespan of your Gambler Hat. Follow the manufacturer’s instructions for cleaning and storage.
  5. Remember, a Gambler Hat is a fashion accessory as well as a functional one. Have fun with your choice and let your personality shine through!



What are the features of the Gambler Hat?

The Gambler Hat is a stylish and functional hat designed for anyone who enjoys casino gaming or has a passion for gambling. It features a unique design with a green color scheme, and the front of the hat displays images of different casino games, such as poker, blackjack, and roulette. The hat also has a brim that provides shade and protection from the sun. It’s made from high-quality materials, ensuring durability and longevity.

What sizes does the Gambler Hat come in?


The Gambler Hat is available in three different sizes: one size fits most adults, a small size for children or those with a smaller head, and an extra-large size for those with larger heads. Be sure to measure the circumference of your head before ordering to ensure a proper fit.

Where can I find the Gambler Hat?

You can easily find the Gambler Hat at various online retailers or through the official product website. Simply search for “Gambler Hat” using your favorite search engine or visit the official website to make a purchase. Don’t forget to check for any promotional deals or discounts that might be available!

Is the Gambler Hat environmentally friendly?

Yes, the Gambler Hat is environmentally friendly. It’s made from high-quality, eco-friendly materials that are not only durable but also kind to the environment. These materials are sourced responsibly, ensuring that the production process has minimal impact on the environment.

How does the Gambler Hat compare to other hats of its kind?

The Gambler Hat stands out when compared to other hats of its kind due to its unique design and stylish color scheme. It also offers great durability and functionality, with a brim that provides shade and protection from the sun. The hat’s eco-friendly materials make it a popular choice among those who prioritize sustainability and environmental responsibility.