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Items 145-192 of 480

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  1. Hats - Black
    Maze Jacquard 504
    Regular Price $60.00 Starting at $30.00
  2. Hats - Black
    Witter Bucket
    Regular Price $75.00 Starting at $37.50
  3. Hats - Charcoal
    Nadel Cap
    Regular Price $70.00 Starting at $35.00
  4. Hats - Black
    Eli Fedora
    Regular Price $85.00 Starting at $42.50
  5. Bailey - Natural
    Glaser Fedora
    Starting at $195.00
  6. Hats - Natural
    Braylon Fedora
    Starting at $170.00
  7. Hats - Tan
    Imlay Fedora
    Regular Price $135.00 Starting at $67.50
  8. Hats - Rust
    Hinx Panama Fedora
    Starting at $225.00
  9. Hats - Natural
    Orsun Raindura Fedora
    Starting at $150.00
  10. Hats - Black
    Rave Sport Bucket
    Regular Price $60.00 Starting at $19.99
  11. Hats - Beige/Cherry Glow
    Wild Trip 504
    Regular Price $60.00 Starting at $30.00
  12. Dayton Raindura® Outback -  Navy/S
    Dayton Outback
    Starting at $138.00
  13. Delafield Cowboy Western Hat - Ivory/ 6 5/8
    Delafield Cowboy Western Hat
    Regular Price $85.00 Starting at $63.75
  14. Derren Cowboy Western Hat - Ivory/ 6 3/4
    Derren Cowboy Western Hat
    Starting at $85.00
  15. Deen Cowboy Western Hat - Ivory/6 3/4
    Deen Cowboy Western Hat
    Starting at $80.00
  16. Alternate View
    Airflo® Mash Up Outback
    Starting at $99.00
  17. 216 Fedora - Fuschia/S
    216 Fedora
    Starting at $170.00
  18. Cavalier Fedora - Black/S
    Cavalier Fedora
    Regular Price $450.00 Starting at $337.50
  19. 313 Boater - Black/S
    313 Boater
    Starting at $180.00
  20. 215 Fedora - Bluestone/S
    215 Fedora
    Starting at $200.00
  21. 214 Fedora - Classic Blue/S
    214 Fedora
    Starting at $165.00
  22. 615 Pork Pie - Dark Green/S
    615 Pork Pie
    Starting at $130.00
  23. 504 Homburg - Black/S
    504 Homburg
    Starting at $170.00
  24. 312 Fedora - Tobacco/S
    312 Fedora
    Starting at $105.00
  25. 202 Fedora - Ash Camo/S
    202 Fedora
    Starting at $120.00
  26. 713 Fedora - Alloy/S
    713 Fedora
    Starting at $140.00
  27. 512 Fedora - Seafoam/S
    512 Fedora
    Starting at $130.00
  28. 410 Bowler - Copper/S
    410 Bowler
    Starting at $120.00
  29. 212 Fedora - Burgundy/S
    212 Fedora
    Starting at $120.00
  30. Alternate View
    Godwin Fedora
    Regular Price $225.00 Starting at $90.00
  31. Renegade® Casville 2X - Fawn/6 5/8
    Casville 2X
    Regular Price $170.00 Starting at $127.50
  32. Alternate View
    Faux Leather Reversible Bucket
    Regular Price $75.00 Starting at $56.25
  33. USA Tropic 507 Ventair - Scarlet/S
    USA Tropic 507 Ventair
    Starting at $50.00
  34. Alternate View
    Bermuda Clery
    Regular Price $65.00 Starting at $32.50
  35. Ore Raindura® Fedora - Army Green/S
    Ore Fedora
    Starting at $138.00
  36. Alternate View
    Baxter Newsboy
    Regular Price $45.00 Starting at $33.75
  37. Country Gentleman Tomlin Fedora - Navy Multi
    Tomlin Fedora
    Regular Price $50.00 Starting at $37.50
  38. Utility Cords Jungle Hat - Navy/S
    Utility Cords Jungle Hat
    Starting at $70.00
  39. Carver Pork Pie - Natural/S
    Carver Pork Pie
    Regular Price $90.00 Starting at $58.50
  40. Alternate View
    Derwent Fedora
    Regular Price $175.00 Starting at $87.50
  41. Alternate View
    Magness Fedora
    Regular Price $180.00 Starting at $117.00
  42. Alternate View
    Warlick Fedora
    Starting at $225.00
  43. Hats - Mushroom
    Balans Roll up
    Regular Price $100.00 Starting at $65.00
  44. Limited Edition - Boyd Fedora - Taupe/S
    Limited Edition - Boyd Fedora
    Starting at $58.00
  45. Quilted Casual - Light Grey/S
    Quilted Casual
    Regular Price $73.00 Starting at $29.99
  46. Faux Fur Bucket - Tan Check/S
    Faux Fur Bucket
    Regular Price $80.00 Starting at $40.00
  47. Furgora Bucket - Black/S
    Furgora Bucket
    Regular Price $80.00 Starting at $40.00
  48. Wool Casual - Black/S
    Wool Casual
    Regular Price $80.00 Starting at $40.00

Items 145-192 of 480

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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.