Coolest Bailey Hats for Fall + Free Shipping
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A Hat For Every Head!

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Men's hats for large heads, in sizes 2X and 3X, can be hard to find. Thank goodness, then for MensHats.com! If you're a hard-to-fit man with a Size 8 head, measuring 25 1/4 inches (or you're shopping for someone with those measurements), you'll be happy with our truly extensive collection of men's hats in sizes 2X and 3X. Every style is represented too, from berets to Greek Fisherman caps and dress hats like the new Stetson Barnstormer, a fur felt fedora with sizes up to [more]

2X & 3X Sizes

Click one of the hats/items below for more information, and use our ZOOM feature to see finer detail.
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Products per Page
Leinburd/Crown Cap Persian Lambswool Winter Hat - The Persian Envoy - image
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Leinburd/Crown Cap...
  $350.00

The Stetson Barnstormer - image
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The Stetson Barnstormer
  $195.00

Stefeno Leather Patch Newsboy - The Randy - image
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Stefeno Leather Patch...
  $195.00

The Deluxe French Beret - image
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The Deluxe French Beret
  $85.00

Kangol Litefelt Trilby - The Wool Player - image
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Kangol LiteFelt...
  $60.00

The Jb Stetson Weathered Cotton Ivy Cap - image
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The JB Stetson...
  $55.00

The Jb Stetson Byers Leather Cadet - image
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The JB Stetson Byers...
  $150.00

Jb Stetson Leather Ivy Cap - image
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JB Stetson Leather...
  $150.00

The Jb Stetson Brooklin Patchwork Newsboy - image
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The JB Stetson...
  $95.00

The Jb Stetson Texas Patchwork Ivy - image
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The JB Stetson Texas...
  $95.00

Jb Stetson Wool Newsboy Cap - The Kennet - image
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JB Stetson Wool...
  $150.00

The Jb Stetson Lenox Trilby - image
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The JB Stetson Lenox...
  $150.00

The Dobbs Raconteur - image
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The Dobbs Raconteur
  $195.00

Borsalino Fur Felt Fedora - The Traveller - image
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Borsalino Fur Felt...
  $295.00

The Bailey Casson - image
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The Bailey Casson
  $125.00

The Bailey Barr - image
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The Bailey Barr
  $110.00

Men's Stetson Fur Felt Casual Western Fedora - The Stetson Weekender - image
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Men's Stetson Fur...
  $175.00

Stetson Fur Felt Fedora - The Stratoliner - image
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Stetson Fur Felt...
  $195.00

Men's Fur Felt Dress Fedora - The Stetson Temple - image
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Men's Fur Felt Dress...
  $175.00

Stetson Fur Felt Fedora  - The Stetson Downs - image
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Stetson Fur Felt...
  $175.00

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  ...continued from above

7 3/4 available, and another from Borsalino, called The Traveller, this unlined open crown offered in a Deep Blue up to size 7 7/8. Stingy brim dress hats are represented in our selection of larger sizes too, with Dobbs offering The Raconteur to size XXL along with Bailey's Casson, a USA-made center crease hat with a stingy 1 7/8" snap brim.

When it comes to flat caps and newsboys in large sizes, we've got you covered with The Randy, a Stefeno leather patch newsboy cap with a sewn down suede brim and satin lining, and an ivy cap from JB Stetson made from weathered cotton that's perfect for bad weather. You can order an XXL newsboy cap in 100% wool too. It's called The Brooklin by JB Stetson, and it's a patchwork cap with a great basketweave, rather like The Texas, the patchwork ivy cap from Stetson, although the latter uses a variety of materials in its panels.

Winter hats need to fit properly in order for your head to stay warm, and we've got a full line-up of cold weather headwear in large sizes, like The Persian Envoy, a dress winter hat made from genuine Persian lambs wool with a woolen pull-down ear band and fully lined with a plush quilted lining for added warmth. You can also get The Diplomat in size XXL, which is similar in style to The Persian Envoy, and is also from Leinburd/Crown Cap. Made of tough, plush sheepskin shearling, you can get extra protection and warmth by pulling the fur trim down around your ears and neck. People who have bought this hat leave five-star reviews that read:

  • This is a very warm and comfortable hat. I have received many compliments, especially on cold winter days. I love this hat!
  • This is a good looking, comfortable and well made hat. I recommend it without reservation.
  • A beautiful, soft, comfortable match to any brown or camel topcoat. Great features for cold weather use without the price of the Diplomat.
  • Bought this hat for my father to ward off the Minnesota winter. It's very stylish. He seems to enjoy it very much.
  • For ultimate protection on a cold winter day, the Leather Bombardier is a classic trooper-style hat from Paul Leinburd of Canada that is made to fit heads up to size 2X. It features rabbit fur in the front which snaps in place and has rabbit fur-lined earflaps for added warmth, secured with a leather tie and buckle. A delighted customer told us: "My husband has a largish head and it's quite difficult finding hats in his size. I gave him the hat as an anniversary gift and he was very pleased that it fit."