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  1. Bailey - Kelp
    Lasham Fedora
    Starting at $145.00
  2. Bailey - Rosewood
    Kinns Fedora
    Starting at $145.00
  3. Bailey - Black
    Bolt Bucket Hat
    Regular Price $200.00 Starting at $150.00
  4. 775 Cowboy Hat - Onyx / S
    775 Cowboy Hat
    Starting at $175.00
  5. Black F23
    Tane Baseball Cap
    Starting at $175.00
  6. Black F23
    Philie Baseball Cap
    Starting at $175.00
  7. Lynton Ivy Cap - Black / M
    Lynton Ivy Cap
    Starting at $175.00
  8. McCrae 3X Cowboy Hat - Black / 6-3/4
    McCrae 3X Cowboy Hat
    Starting at $160.00
  9. Horan Fedora - Black / S
    Horan Fedora
    Regular Price $240.00 Starting at $180.00
  10. Hats - Black
    Max Fedora
    Starting at $100.00
  11. Hats - Black
    Scorsby Fedora
    Starting at $100.00
  12. Boreal Fedora - Black/Ash / S
    Boreal Fedora
    Regular Price $225.00 Starting at $168.75
  13. Camel
    Portsea Cloche
    Regular Price $250.00 Starting at $187.50
  14. Hats - Natural
    Quil Derby
    Starting at $195.00
  15. Winstone Raindura Fedora - Black / S
    Winstone Raindura Fedora
    Starting at $135.00
  16. Camel
    Apollo Baseball
    Regular Price $210.00 Starting at $168.00

Items 1-16 of 99

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Shop Iconic Men’s Hats

We never limit fashion when it comes to our men’s hats. That’s why our collection of men’s caps and hats was curated so you could find the hat perfect for you and your unique look. Browse all of our men’s hat styles to find your favorites, or filter our options by color, shape, size, and more to find the exact hats that fit your style. Whether it’s our fedoras, ivy and flat caps, classy beanies, or baseball caps, we promise you’ll find that piece that expresses your distinctive style.

Timeless Fashion carries classic and modern men’s caps and hats from leading brands like Kangol, Bailey 1922, Country Gentlemen, and more. We’re your ultimate guide in the world of men’s headwear, and we can help you find the right style for your facial shape and structure. We offer the finest trendy hats so that you can rest assured you’re looking your best. With timeless pieces like trilby hats and bucket hats, we offer many clean looks and classic shapes that work with a variety of outfits.

Shop The Latest from

Masculine fashion is our specialty. With our wide variety of men’s hats, you’re sure to find something to suit your look. Compliment your hat with an entire outfit from our collection of men’s clothing and accessories.

Plus, with our Sezzle payment program, you can pay for your new style on a schedule that works for you. Explore more and become a Rewards Member today!

Frequently Asked Questions

1. Why are men’s fedoras so popular?

Men’s fedoras are classic men’s hat styles that can instantly make any outfit more sophisticated. They’re highly versatile and you can dress them down or up depending on the occasion. These hats also protect from the sun by blocking harmful ultraviolet rays, which may damage your skin.


2. What makes Bailey 1922 one of the most popular brands for men’s hats?

Bailey 1922 remains a top brand for men’s caps due to their sophistication, craftsmanship, and heritage. Since 1922, these hats have stood out for their fine quality and ability to help people express their individuality. The company also offers a wide variety of hats that suit various preferences and occasions, including cowboy hats, straw hats, and fedoras.


3. What are some of the most popular clothing items and accessories men shop for when purchasing hats?

Some of today’s most popular men’s accessories range from backpacks to fleece hoodies and hoodie pullovers. Men’s hat lovers also look for comfortable t-shirts (including waffle tees), track jackets, jogger pants, popovers, and down or fleece jackets.