Best Gambler hats for men

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Adventurous, spontaneous, impulsive, confidence is the words used to describe gambler hats. These are not the hats for everyone. But if you have a personality similar to that hat, it will surely enhance your look and take you to the next level. Gambler hats are western-style hats with a distinctive crown on top with ample brims. This hat is the silent words of telling people that you are a cool and confident high-roller.

Having said that, it can be difficult to buy a gambler cowboy hat as they are often sold as souvenir and are often overpriced for their concept. So here, we offer you some choices. These hats are highly ranked by the buyers. Most of the time, their prices are equal to the quality that they have.

01. Stetson Men’s Hawk Crushable Wool Gambler Hat – Swbkhk-7830 Black

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This cool gambler hat for men is made from 100% soft wool felt. It’s also water resistant and is crushable. What can be better than a hat that will keep you warm in the cold days and dry on the rainy days?

The hat is silver-toned. It features a leather hatband with a black leather tail. This is a classic gambler hat style. That hat can pop back into its original shape easily despite suffering harsh weather so it will always sit nicely on your head. Just by looking, you can tell that it’s a hat of quality and look. That hatband is placed off-center purposely which adds extra to the playful personality of the bearer.

The hat has been receiving feed backs that it’s a little too expensive than the quality that it offers. Of course, as mentioned, this is the case for mot gambler hat. But this hat is still better compared to other overpriced hats.


02. Eddy Bros. Men’s Gambler Hat

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Come in only black, this gambler hat is also made from 100% wool felt, it has a unique leather headband with small pennant-like items around the hat. It also features a small leather tail on the left side. This gambler hat will take care of the excess sweat on your forehead and hair by the sweatband located around the inside of the hat.

This hat has a gambler style with a rustic American aesthetic. The medallions around the hatband make the hat shiny, reflecting the confident style of the bearer. It’s also warm to wear in the cold day as the wool felt will keep you tight and cozy.

But be careful when wearing this hat as the medallions can drop off sometimes. And if one of them is lost, the rest will look unsystematically.


03. Dorfman Pacific Men’s Rush Straw Lightweight Casual Wide Brim Gambler Hat

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This straw gambler hat will add extra to the playfulness of the wearer. It’s made of 100% natural rush straw. The material makes the hat light and breathable. The straw fibers work very well in repelling the sunlight. The bride brim keeps the sun off your eyes and your face.

This hat can be worn with a beach outfit setting. Also, you can wear it when you’re out for fishing, gardening, hiking, sunbathing. The straw fibers leave a lot of small hole for air circulation. It deals well with the sweating. Also, the hat won’t have a bad odor even if the wearer is a sweater. The hat is available in 4 sizes for men.

Straw hats are easily bent and damaged but it’s also easy to reshape them. But remember to buy straw gambler hats from reliable source. They should be kept in a box, not a bag, to avoid getting damaged.


04. Conner Hats Men’s Quincy Wool Gambler Hat

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  • 3 inches brim
  • 25 inches crown

This is a water-resistant gambler hat made in Australia (with Australian wool). It’s crushable and compact so you can just fold it and put in your luggage when traveling. The hat includes an inner cotton headband so it can fit nicely on your head while adding extra warmth in the cold days. The sweatband is made of cotton so it’s absorbent.

The hat is comfortable to wear. Needless to say, the style is also great. This crushable hat really makes traveling and packing easier. The price is quite high compare to what people are willing to pay for the hat. But trust me, it is worth every penny.

However, the hat can be too hot to wear on sunny days. The wool and cotton leave little space for air circulation. Be mindful of that.


05. Black Creek Men’s Gambler Straw Hat – Bc9016

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The hat comes in two colors: black and ivory. It’s more like a travel and party hat than a gambling hat. The hat is made of high quality Toyo straw. It features a braided accents hatband. There are a lot of holes (by design) around the hat which allows air circulation.

This hat will give you a lot of sunshade with its tight weave. The manufacturer packs it nicely and carefully because straw hats can lose their shape easily. The color of the hat won’t make you stand out in a crown but would definitely get you a lot of attention.

Just like any other hats made from straw, you have to be very careful when using it. Don’t hold it with a firm grip. Hang it somewhere so that you won’t accidentally sit on it. They can lose their shape easily.


06. M&F Western Unisex Gambler

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For the last hat on the list we offer you a unisex hat for true western gamblers. With only on color: black, the hat makes you look playful and unpredictable. Wear this hat and sit at a poker table, people will definitely give you some thoughts.

The great thing about this hat is that it is crushable, which makes traveling much easier. You can easily roll it up and pack it in your suitcase. It will pop back into the original shape when you want to wear it. The hat is also made from wool. It can keep you warm in the cold days.

The only thing you need to be aware of when using this hat is that it needs to be hand-washed. The hat can lose its colors easily if you toss it in a washing machine.


Gambler hats are probably a unique hat among all the hats for men. They are easy to distinguish due to the curvy shape of the brim and the tail on the hatband. Whether for fashion purpose or protection purpose, take your time when selecting a hat. They are expensive and when they don’t look good on your head, there is little you can really do about it.

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