Coolest Bailey Hats for Fall + Free Shipping
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Wool Hats & Caps image
The wool hats and caps in our Fall/Winter collection have truly never been finer with brand names like: JB Stetson offering The Patch, a wool blend patchwork cap with tie print satin lining; Christys' bringing you The Claudius, a cushion front wool cap with sewn down brim and snap peak; and Goorin, with its big brim wool blend newsboy cap. More new caps for the season include an ivy cap in a [more]

Wool Hats & Caps

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Bailey Wool Ivy Cap - The Port - image
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Bailey Wool Ivy...
$60.00   $42.00

Kangol Newsboy Cap - The Donegal Tweed Ripley - image
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Kangol Newsboy Cap
  $55.00

Kangol Herringbone Peebles Ivy Cap - image
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Kangol Herringbone...
  $75.00

Bailey Wool Ivy Cap - The Bailey Lord Ivy - image
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Bailey Wool Ivy...
$65.00   $45.50

Bailey Wool Ivy Cap - The Bailey Lord Herringbone - image
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Bailey Wool Ivy...
$65.00   $45.50

The Jb Stetson Wool/Suede Ball Cap - image
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The JB Stetson...
  $30.00

Jb Stetson Ivy Cap- The Patchwork Ivy - image
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JB Stetson Ivy Cap-...
  $55.00

Jb Stetson Newsboy- The Patchwork Newsboy Cap - image
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JB Stetson Newsboy-...
  $55.00

Kangol Wool Ivy Cap - The Peebles - image
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Kangol Wool Ivy...
  $55.00

Jb Stetson Ivy Cap - The Herringbone Modesto - image
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JB Stetson Ivy Cap
  $95.00

Doria Patchwork Ivy Cap - The Fiorentino - image
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Doria Patchwork Ivy...
  $95.00

Jb Stetson Hatteras - The Wool/Cashmere Hatteras - image
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JB Stetson...
  $95.00

Men's Wool  Ivy Cap - The Scala Wool Felt Ivy - image
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Men's Wool Ivy...
  $35.00

Jb Stetson Newsboy - The Herringbone Hatteras - image
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JB Stetson Newsboy
  $95.00

Christys' Wool Blend Newsboy - The Scotch - image
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Christys' Wool Blend...
$75.00   $45.00

Christys' Patchwork Ivy Cap - The Bedlam - image
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Christys' Patchwork...
$85.00   $42.50

The Capas Big Apple Wool Tweed Cap - image
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The Capas Big Apple...
  $40.00

Kangol Woolen Winter Ivy Cap - The Classic Ivy - image
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Kangol Woolen Winter...
  $45.00

Christys' London Wool Ivy Cap - The Tiber - image
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Christys' London Wool...
$65.00   $32.50

Christys' Wool Rex - The Adriatic Stingy Brim Hat - image
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Christys' Wool Rex
  $85.00

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  ...continued from above

handsome wool blend from Stetson with seam piping, as well as The Donegal Tweed Ripley, a Kangol newsboy cap (with contrast colored stitched down brim and leather tab with d-ring and Kangaroo emblem). There's also a newsboy-style Gatsby cap from Goorin that's sure to please. The eight panel cap is in a lightweight wool blend fabric and features a sewn down brim. The interfaced sweatband with slight stretch allows for a comfortable, snug fit.

Customers love The Wool/Cashmere Hatteras from JB Stetson and have left multiple five-star reviews for this newsboy crafted from a blend of virgin wool and cashmere:
  • I have had a great deal of trouble buying good hats. I wear Size 7 7/8 to 8, which has limited my choices over the past 30 years. This hat, however, fits perfectly. There is enough material in the top to have it fit how it should. Very nice material, fits well, and I cannot praise it enough.
  • Excellent, rich, handsome cap.
  • Very fine quality hat. Wonderful blend of materials made with true craftsmanship. Fits well and looks great.
  • Just what I was looking for. Fabric is beautiful thanks to the nice blend of cashmere and wool, and it should wear well. Husband loves this hat!
  • This hat fits perfect and the more I wear it the better it looks. So happy with my choice!

The attention to detail and excellent workmanship in caps by JB Stetson is evident too in The Herringbone Hatteras, a 100% wool newsboy. The brim is stitched down at three different points on this wool cap for a perfect fit and finish. There's a leather patch at one side and the lining is a comfortable cotton/poly blend, plus it comes in a handful of colors. Some five-star reviews for this newsboy read:
  • I have looked for this hat for years. Fits great and looks great and it's a Stetson.
  • This is an excellent Newsboy Cap. I have worn this cap every day since I recieved it.
  • Outstanding newsboy. Extremely well made and superb styling. Couldn't be happier with my purchase. Can't wait till cooler weather so I can wear it every day. Highly recommend this hat.
  • I love this cap. Stetson never disappoints.
  • Wonderful replacement for one worn many years. Fit is exact.

Kangol's another top brand introducing a new ivy cap, and this year they've outdone themselves with The Peebles, a fancy Italian wool tweed cap with a sewn down brim. Bailey of Hollywood has a couple of new caps for the season, one being The Port, a tasty wool ivy cap with contrast side panel and brim. For a tried and true cap, there's that one-of-a-kind Borsalino ivy, The Fiorentino, a woolen patchwork cap crafted from the milliner's finest wools. One happy customer calls it a "slick cap" and his five-star review reads: "This is a very nice cap. I am getting compliments just wearing it to the local store. Ladies seem to notice it the most."

Woolrich is another top brand represented here, offering The Wool Blend Ascot, a traditional Irish cap from the hat maker's Heritage Collection. The satin lined cap is made from warm 503 Hunt Cloth and customers love it, leaving reviews that read:
  • I was looking for a dressy hat I could wear in the winter. This hat is great for that purpose.
  • True to size, excellent hat...warm and stylish. Woolrich quality.
  • Very happy with my purchase. The hat fits great and looks good too. I'm glad I bought it.

Wool caps from Christys' London include The Tiber, an ivy cap in 100% wool done in a handsome herringbone pattern. With The Milvian, a woolen longshoreman cap, you've got a choice of Brown or Charcoal herringbone. The silhouette on this cap is slightly longer than that of the traditional ivy, and looks very sharp. There's also a wool blend driving cap in a great patchwork pattern you may wish to consider. With its sewn down cushion front and jacquard lining, there's nothing crazy about The Bedlam--except maybe its good looks.

From Capas Caps, we've got another tweed cap that is a perennial favorite. The 8/4 panel newsboy is made in the USA, from 100% wool tweed and it offers a relaxed silhouette. Yet another snazzy Capas cap goes by the name of The Big Apple. You may have seen the wool melton and leather versions, but this particular rendition is made from wool tweed in Brown, perfect for the season.

A satisfied customer said "the Borsalino Rex is a great hat and it's got a good fit." This traditional tweed walking hat is made from a finely woven 100% Donegal wool, and it rex features a snap brim and quilted lining. When it's frosty outside, caps with earflaps liked The Earlap from Borsalino (a winter ivy cap with hidden knitted earlaps) and The Classic Ivy (100% wool cap with woven sweatband from Kangol) are nice to have on hand (and on your head).