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  1. Hats - Black Hills
    Black Hills Gambler
    Regular Price $65.00 Starting at $48.75
  2. Melton Gambler
    Melton Gambler
    Starting at $160.00
  3. Rockett Raindura® Gambler
    Rockett Raindura® Gambler
    Starting at $140.00
  4. Chancy 2X
    Chancy 2X
    Regular Price $170.00 Starting at $127.50
  5. Ellsworth Gambler
    Ellsworth Gambler
    Starting at $150.00
  6. Gambler
    Starting at $70.00
  7. Joker Western Hat
    Joker Western Hat
    Starting at $110.00

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Gambler Cowboy Hat

Shop men’s gambler hats made of top-quality wool felt, seagrass, and straw to make sure you’re ready for anything. It’s time to go on an adventure you’ll never forget. At, it’s our mission to provide you with a premier collection of men’s hats to enhance your style. If you’re looking for something that evokes the wild freedom of the untamed West, a gambler hat could be the perfect choice for you. With their distinct oval-shaped crown and brim, they’re very similar to a regular cowboy hat but often include extra embellishments and details.

Striking Statement Pieces

A gambler hat offers you a distinctive fashion choice. It imbues you with a confidence and boldness that defines your style. These men’s gambler hats aren’t for those who play it safe! We carry gambler cowboy hats that are carefully crafted and designed for the summer, spring, and winter hat seasons so you can look your best no matter the time or place. With leading brands like Country Gentlemen, Bailey Outdoors, and Renegade Hats, you can find a high-quality statement piece that fits your aesthetic.

Unleash Your Inner Renegade

The gambler is a rugged and stylish hat that only gets more sophisticated with the passing years. With this timeless style, you’ll personify the same risk-taking, forward-thinking essence the hat’s name suggests. Check out our selection of high-quality men’s gambler hats to discover unique styles and specialty designs.

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Frequently Asked Questions

1. Why are gamblers so popular among men?

Many men love the gambler cowboy hat because its versatile and classic look suits both formal and casual occasions. The most popular gambler cap colors include gray, beige, tan, and black. Black is an especially in-demand hue among men seeking to showcase a sophisticated and mysterious look, while beige and tan trendy hats stand out for being light-hearted and casual. Gray is a balanced and neutral hue that works well with cool and warm tones.


2. Why are some gamblers made with seagrass?

Seagrass is eco-friendly and natural, making it an excellent hat material choice for sustainable hat lovers. Seagrass is also stain-resistant, durable, breathable, and lightweight, making seagrass gamblers ideal for keeping men comfortable and cool in the summer.


3. How old are gambler hats?

Gambler hats have been around since the 1800s, when riverboat gamblers attempting to copy wealthy landowners’ fashion popularized them. Farmers and other gentlemen also wore these hats since they appreciated the hats’ versatile and classic look. You can spot gambler hats in Maverick, a 1957-1962 television series starring James Garner, and Gone with the Wind, a 1939 movie starring Clark Gable.