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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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Winter Flat Caps

1 - 28 of 106 Products
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…relatively lightweight nature makes this a great cap for both autumn and winter.    Approx. 9 3/4" Length, Flat 10" Width, Flat 1 3/4" Double Snap Bill   Made of: 100% Virgin Wool   Made in Italy Classic Ivy Cap Design Windowpane Plaid Pattern Bailey Side Pin Grosgrain…

$85.00

…original Kangol. It's iconic and is made for colder weather. Bring the style this fall/winter season!   Approx. 9 1/2" Length, Flat 8 3/4" Width, Flat 2" Sewn Bill   Made of: 43% Modacrylic 37% Wool 11% Acrylic 9% Nylon   Original 504 Design Tonal Boiled Wool Stripe…

$60.00
Available Colors:
  • DARKFLANNEL

…Melton Wool Earflap Ivy Cap by Wigens is a comfortable and attractive wool ivy cap with earflaps. The warm earflaps are lined in soft fleece and the quilted polyester lining help protect you from the bitter winter cold. Made of 100% wool, the Melton Wool Earflap Ivy Cap by Wigens offers unmatched…

$120.00
Available Colors:
  • BLACK
  • CAMEL

Cap gives off an air of confident intelligence with a sharp yet refined style. Featuring a fine smooth nappa leather, this flat cap is known for its softness and durability. Nappa leather is water vapor permeable and therefore provides an excellent heat exchange, perfect for the Fall and Winter

(5)
$119.00
Available Colors:
  • CHOCOLATEBROWN
  • BLACK

…from bamboo, and is considered more whickable than cotton. It has insulating properties keeping you cooler in the summer and warmer in the winter, feeling gentle and smooth next to the skin.   The protection panels allow you to have multiple looks! They're both optional and removeable,…

$7.95
Available Colors:
  • CAMOUFLAGE

…Kangol logo side pin, the Knit Panel Wool Blend 504 is lightweight and unlined - ideal for crisp fall and winter weather.    Approx. 9 3/4" Length, Flat 10 1/2" Width, Flat 1 7/8" Sewn Bill   Made of: 40% Viscose 35% Wool 25% Modacrylic   Classic 504 Shape Seamless…

$41.25
Available Colors:
  • BLACK
  • FLANNEL

…and plush, quilted satin lining this cap will make a great addition to any flat cap lover's collection.    Approx. 9 1/2" Length, Flat 10 1/4" Width, Flat 2" Snap Bill   Made of: 100% Italian Wool   Limited Edition Classic Ivy Cap Design Classic Houndstooth Pattern…

(5)
$34.95

…a stretchy elastic sweatband that matches the color of the cap's stripes. Sporty, stylish and warm, the new Code Stripe 504 is a definite must-have this fall and winter!    Approx. 9 1/2" Length, Flat 10" Width, Flat 1 7/8" Sewn Bill   Made of: 50% Lambswool 50% Modacrylic …

$60.00

  For whatever your plans are, check out the Winter Stars Plaid Ivy Cap from Goorin Bros! Packable and crushable in build, this ivy can go with you anywhere, perfect for travel. The windowpane plaid pattern is stylish and eye-catching, and the intricate satin lining is so comfortable. …

$60.00
Available Colors:
  • BLACK

…classic width wale, this cap is perfect for the cooler fall and winter seasons. Trimmed with a small New Era flag logo side pin and cotton lining, this style boasts an incredibly soft and pliable sewn leather bill.   Approx. 9 3/4" Length, Flat 9 1/2" Width, Flat 2" Sewn Leather Bill …

(1)
$50.00
Available Colors:
  • BLACK
  • TAN

…with an extended sewn bill and satin lining. Perfect for fall and winter, the Cheesecutter Wool & Cashmere Ivy Cap will add sumptuous softness and style to your look.    Approx. 9 1/2" Length, Flat 10" Width, Flat 2 1/4" Extended Sewn Bill   Made of: 14% Cashmere 86%…

$105.00
Available Colors:
  • BLACK
  • WINE

…like herringbone and plaid. The Donegal Tweed Herringbone Patchwork Ivy Cap features both of those patterns. This unique flat cap features a colorblock of patterns in each patch. Add a nice pop of color to your Fall and Winter wardrobe.   Approx. 2 1/4" Sewn Bill 9 3/4" Diameter …

(5)
$86.00

…a clean and updated look. Perfect for fall and winter, the Smit Tweed Ivy will keep you warm AND in style.    Approx. 10" Length, Flat 9 3/4" Width, Flat   Made of: 55% Wool 45% Polyester   Breed® Collection Cap 5-Panel Design Bailey Staple Side Pin Comfort Sweatband…

(1)
$67.00
Available Colors:
  • CAMEL
  • NAVYBLUE

…detailing, this ivy cap isn't your run-of-the-mill flat cap. Its thick woolen design and tuckaway earflap provides warmth for your head and ears in a classic pattern ideal for fall and winter that always looks dapper.    Approx. 9 3/4" Length, Flat 10" Width, Flat 1 5/8" Sewn Bill …

(2)
$80.00

…and hand crafted detailing, this ivy cap isn't your run-of-the-mill flat cap. Its thick woolen design provides warmth for your head in a classic pattern ideal for fall and winter that always looks dapper.    Approx. 9 3/4" Length, Flat 10" Width, Flat 1 5/8" Sewn Bill   Made of:…

(2)
$68.00

…your winter wardrobe with the Chunky Knit Infinity Scarf from sur la tete.   The continuous one loop warm acrylic knit scarf is the perfect compliment to any wardrobe – but particularly with sur la tete's wonderful selection of fall and winter hats.   Approx. 34" Length, Flat 68"…

(4)
$15.95

…dress hat design, the Silk Bow Wool Felt Lampshade Hat by Toucan is a lovely new dress hat for fall and winter. Crafted in the USA of soft and packable wool felt, this hat boasts a square crown (flat top, straight sides) and an elegant down-turned wide brim. Adorned with an oversized distressed silk…

(1)
$95.00
Available Colors:
  • BLACK
  • CAMEL
  • CHARCOAL
  • NAVYBLUE

…a small wooden Bailey side pin is placed at the cap's left side. Perfect for fall and winter, the Salko Cotton Newsboy Cap has a singular look you need to add to your Bailey cap collection!    Approx. 9 5/8" Length, Flat 10" Width, Flat 1 7/8" Extended Sewn Bill   Made of: 100%…

(1)
$60.00
Available Colors:
  • DENIMBLUE

…Kangol logo at the back and stylish fillet 'head band' the Hawker Corduroy is your ticket to style this fall and winter!    Approx. 10 1/2" Length, Flat 9 3/4" Width, Flat 1 3/8" Sewn Bill   Made of: 98% Cotton 2% Spandex   Standard Wale Corduroy Finish Hybrid…

$64.00

…for the ideal warm coverage during cooler fall and winter months. Classically trimmed with a rounded single snap bill and quilted satin lining, the Rochester has a sleek and clean look.   Approx. 9 1/2" Length, Flat 10 1/4" Width, Flat 1 3/4" Single Snap Bill/Brim (Measured from size…

(1)
$34.95
Available Colors:
  • NAVYBLUE

…construction. Complete with a textured body and slouch design, this beanie will keep you fashionably warm all winter long.   Approx. 7 1/2" Diameter, Flat 10" Length, Flat   Made of: 100% Acrylic   Jaxon Tag Slouchy Fit Unlined   Size: One Size Fits Most…

$9.95
Available Colors:
  • BEIGE
  • BLACK

…crafted in Italy, this cap features a lightweight wool blend fabric that transitions easily from fall to winter.    See the Bailey Lord Cap's Solid version or classic Herringbone version to complete your collection!   Approx. 8 1/2" Diameter 1 7/8" Flat Bill   Made of:…

(3)
$85.00
Available Colors:
  • BLACK
  • BROWN
  • GREEN

  Top off your look this autumn and winter with the velvety softness and luxurious sheen of the new Wyman Velvet Newsboy Cap by Bailey. Part of their innovative Breed® Collection of hats and caps, Wyman boasts a more structured 8-panel design complete with a stylish extended bill. Its soft…

$64.00
Available Colors:
  • BLACK
  • BURGUNDY
  • NAVYBLUE

…ascot cap finish, this cap hugs the contours of your head and has a fuller crown. Trimmed with a luxe quilted satin lining and knit satin sweatband, the Herringbone Harris Tweed Wool Ascot Cap by Stefeno is a stunning cap perfect for fall and winter.    Approx. 9 3/4" Length, Flat 9 1/2"…

(2)
$105.00

…Ivy Cap by Wigens offers stylish and functional protection from the cold. Made from 100% wool in a rich true brown hue, the Vilgot Melange Melton Cap features versatile tuckaway earflaps you can wear over your ears or tucked into the hat. Sure to become your favorite go-to cap during cold winter

$125.00

…who prefer a bit more cap up top, the Ollie Wool Blend Newsboy Cap answers the call and will pair well with warm-toned fall and winter clothing.    Approx. 11" Length, Flat - Back to Front 10 1/2" Width, Flat - Side to Side 2" Snap Bill/Visor (Measured from size M cap)   Made of:…

(1)
$39.00

…the Galvin Striped Twill Wool Newsboy Cap features a stylish striped tweed pattern perfect for the season. Featuring the Galvin's classic newsboy design, this cap boasts an 8-panel crown, Bailey back pin and a double snap bill. Great for cool fall and winter months, the Galvin Striped Twill Newsboy…

$100.00
Available Colors:
  • CHARCOAL

  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. 2" Snap Bill  9" Diameter   Made of: 40% Wool 60% Polyester   Removable Jaxon Side Pin Padded Bill Sweatband…

$24.95
Available Colors:
  • BLACK

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