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    • Small
      Pequeuño
      Size
      6
      3/4
      -
      6
      7/8
      Tamaño
      21
      1/8
      "
      -
      21
      1/2
      "
      54
      cm
      -
      55
      cm
    • Medium
      Medio
      Size
      7
      -
      7
      1/8
      Tamaño
      21
      7/8
      "
      -
      22
      1/4
      "
      56
      cm
      -
      57
      cm
    • large
      Grande
      Size
      7
      1/4
      -
      7
      3/8
      Tamaño
      22
      5/8
      "
      -
      23
      "
      58
      cm
      -
      59
      cm
    • X-Large
      X-Grande
      Size
      7
      1/2
      -
      7
      5/8
      Tamaño
      23
      1/2
      "
      -
      23
      7/8
      "
      60
      cm
      -
      61
      cm
    • XX-Large
      XX-Grande
      Size
      7
      3/4
      -
      7
      7/8
      Tamaño
      24
      1/4
      "
      -
      24
      5/8
      "
      62
      cm
      -
      63
      cm
    • XXX-Large
      XXX-Grande
      Size
        8
       - 
      8 +
      Tamaño
      25
      "
      -
      25
      3/8
      "
      64
      cm
      -
      65
      cm
  • This is a General Hat Sizing Chart: Please read each hat product page for further sizing information.
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Save up to $16 | End of Winter Sale | CODE: WINTER
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Winter Hats

1 - 28 of 87 Products
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  Finally Kangol's popular Tropic Monty Beret is available in a warm wool version perfect for fall and winter! Field Marshal Montgomery, for whom the hat is named, wore a Kangol Beret as he commanded Allied troops in World War II. This Kangol military beret has made a fashionable transition…

(8)
$55.25
Available Colors:
  • BLACK
  • DARKBLUE
  • RED
  • TAN

…  The new Knightsbridge Italian Wool Ivy Cap features 100% Italian wool and a black/tan variegated herringbone pattern. Part of the Baskerville Hat Company's new Fall/Winter line, the Knightsbridge Ivy is a cozy and classic option for the season. Finished with a single-snap bill and plush,…

(2)
$34.95

  FINAL SALE   The Jaxon Herringbone Trapper is an excellent way to keep stylishly warm this winter. The earflaps which can be worn up, or down on those particularly cold days you know are coming are lined in a soft faux fur.   Approx. 7 1/2" Earflap Length   Made…

(10)
$14.95
Available Colors:
  • BROWN

…the Scala Boho Wool Felt Swinger Hat needs little embellishment. Its raw edge brim gives the hat a clean finish while its slightly floppy nature gives it its relaxed boho charm. Available in great colors perfect for autumn and winter, the Boho Wool Swinger Hat is a chic way to complete almost any…

(1)
$56.00
Available Colors:
  • CAMEL

…tucked back into the hat's crown when not in use. Bailey's exclusive LiteFelt® finish gives the hat its soft and packable/crushable nature while also making it water repellent. Ideal for colder (and wetter) fall and winter months, the Joe Eder Wool LiteFelt Western Hat by Bailey has the…

(5)
$114.75
Available Colors:
  • SERPENT
  • BLACK

…confidence with the Gain Wool Felt Fedora Hat from Brixton! Featuring a soft wool felt fedora designed with a pinch front center dent crown, trimmed with a sleek grosgrain ribbon hat band and a stingy snap brim, this fedora will get you through fall and winter in total style!   Approx. 4"…

$63.75

…perfect for windy winter days. Equipped with a chin cord, this hat will stay right where it's suppose to be - on your head.   Approx. 4" Teardrop Crown 3 1/2" Underwelt Curved Brim   Made of: 100% Wool Felt - Soft, Packable Finish   Faux Leather Hat Band Faux Leather…

(10)
$59.95
Available Colors:
  • BLACK

…Felt Floppy Hat is a stylish new design perfect for all and winter. Featuring a round crown with a medium-sized brim, Mullins is adorned with a wide grosgrain hat band and faux fur poms at the side. Inside, Mullins features a drawstring grosgrain sweatband that adjusts the hat's fit.    …

(1)
$73.00
Available Colors:
  • BLACK
  • PLUM
  • LEOPARD

  Kangol's Furgora Cuff Beanie Hat is the newest in the line for fall/winter. Fashioned after the classic cuff beanie silhouette, furgora yarn amps up the volume with its uber soft texture. Turn the cuff down for a more slouchy beanie look on those toasty nights in from the cold.   …

$68.00
Available Colors:
  • BLACK
  • IVORY

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Winters Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably…

(3)
$164.05

  Summer, Winter, Autumn or Spring, whether skies are gray or blue, we've got you with the Women's Every Season Covered! The Chloe Wool Felt Cloche Hat will keep you warm yet stylish during the colder months, while when it pours you can pull out the Nylon Rain Bucket Hat. To round it all out,…

$44.96

…extent of our Russian - home of the Cossack Hat. Due to the crazy demand, we've brought the Jaxon Cossack back in stock! The extremely soft faux fur hat comes complete with a fully quilted satin lining along with cotton/fleece earlaps for those cold winter days.   Approx. 2 7/8" Earflap…

(43)
$44.95
Available Colors:
  • BLACK

  Featuring a classic herringbone pattern bespeckled with multi-colored flecks, the Cambridge Herringbone Wool Ivy Cap by Jaxon Hats is a singularly stylish fall/winter cap. Crafted of a medium-weight wool blend, the Cambridge is styled in the classic ivy cap tradition with a single-snap…

(17)
$29.95
Available Colors:
  • GREEN
  • NAVYBLUE

…Felt Fedora Hat is a handsome new fedora style crafted of a fine fur and wool blend. Trimmed with a traditional grosgrain ribbon hat band, deluxe side feather and Dobbs side pin, the Prescott features a classic teardrop crown and 2 1/2 inch snap brim. Dress up your look this fall and winter with the…

(2)
$162.00

…Call us at 1-888-847-4287 for help with sizing.   Limited Edition   The Hampstead Japanese Wool Ivy Cap is part of Baskerville Hat Company's newest Fall/Winter line. Made of 100% Japanese Wool, the Hampstead is sleek and classic while providing warmth and comfort during the…

(2)
$34.95
Available Colors:
  • CHARCOAL

…M = 7 1/4 L = 7 1/2 XL = 7 3/4 XXL = 8 The multi-tone checked Austen Wool Check Square Bill Ivy Cap by Baskerville Hat Company is perfect for fall and winter! And not only because of this classic pattern. Made of 100% Italian wool for the colder months, pop this ivy on the second you fell…

$34.95

  Made in Belgium with Genuine Irish Virgin Wool Donegal Tweed   Meet your new favorite winter accessory: City Sport Caps’ Herringbone Squares Donegal Tweed Wool Ivy Cap. Made in Belgium of 100% genuine virgin wool Donegal Tweed (handwoven in Donegal, Ireland), this iconic ivy cap…

$121.95
Available Colors:
  • TAN

  FINAL SALE   Get comfy cozy with the Blanket Fleece Packable Bucket Hat by Brixton Hats. This hat emphasizes coziness with its fleece finish that reminds us of fuzzy blankets on a cold winter's night. Interior is unlined with a tonal underbrim and elasticized sweatband.   …

$24.50
Available Colors:
  • BLACK
  • BURNTORANGE
  • DESERT

…the 100% wool felt Ammon Wool Felt Teardrop Fedora Hat by Bailey is astonishingly silky to the touch. A classic teardrop crown (aka C-Crown) and all around downturned brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband…

(1)
$164.05

  Made of 100% wool, Village Hat Shop brings you the timeless Wool Fashion Beret in a wide assortment of colors. Sleek and simple, this seamless wool beret is topped with a small tonal tassel. Wear it tilted to either side of your head, centered or towards the back - the Wool Fashion Beret adds…

(113)
$14.95

  For those of you who need some extra insolation this winter, we have the Faux Fur Trapper Hat by Kangol. This hat is the next best thing to walking around with your own personal heater! Features all-over faux fur, a thick quilted lining and earflaps that can be worn down or tied up.  …

$80.75
Available Colors:
  • BLACK

…Harris Tweed wool and made in Italy, the Herringbone Harris Tweed Wool Ascot Cap by Stefeno is a study in quality, craftsmanship and tradition in hat making. Spun, woven and dyed by hand in the Outer Hebrides of Scotland following age-old traditional methods, Harris Tweed wool is world-famous for…

(4)
$117.95

  Made in Belgium with Genuine Irish Donegal Tweed Virgin Wool   Village Hat Shop Exclusive   Get that old school newsboy look with the Herringbone Donegal Tweed Wool Newsboy Cap by City Sport Caps. Featuring a distinctive herringbone pattern, this flat cap is sure to envoke…

(1)
$109.00
Available Colors:
  • COGNAC
  • OFFWHITE

…option, then look now further than the Toucan Collection's Vegan Wool Felt Gaucho Hat. Finished to appear as if it's made of wool felt, this hat is actually completely vegan. In the oh-so popular gaucho design, this hat is fashion without the price tag! A must for your fall/winter wardrobe. …

$56.00
Available Colors:
  • SAND

  Keep your head warm with the quintessentially classic Harlem Wool Ivy Cap by Jaxon Hats. Stay warm while looking stylish all fall and winter long.    Approx. 9" Diameter 2" Single Snap Bill   Made of: 40% Wool 60% Polyester   Removable Jaxon Side Pin Padded Bill…

$29.95
Available Colors:
  • BLACK
  • CHOCOLATEBROWN
  • BURGUNDY
  • OLIVEGREEN
  • CHARCOAL

…Shepherds of the same name, Bearn.  They first hand knit the beret and then felted the wool in mountain waters to create a hat that protects against the sun and harsh winters. Basque became the more popular term when Napoleon III, noticed it upon the laborers working on his Palais de Biarritz. The…

(42)
$89.95
Available Colors:
  • BLACK
  • NAVYBLUE
  • RED

…Collection, the Stetson Whippet Fur Felt Fedora Hat is created with the finest Royal Deluxe Quality fur felt. Crafted with a smooth and delicate finish, this handsome fedora works well with many winter outfits, jackets and coats. The tonal grosgrain hat band wraps around the crown ending in a side…

(8)
$249.99
Available Colors:
  • TAWNY
  • CARIBOU
  • BLACK

  Made in Belgium with Genuine Irish Virgin Wool Donegal Tweed   Village Hat Shop Exclusive   The Donegal Tweed Large Herringbone Newsboy Cap by City Sport Caps offers an old school look. Featuring a large distinctive black and white herringbone pattern, this flat cap is…

(1)
$109.00
Available Colors:
  • BLACKWHITE

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