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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 97 Products
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  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

…plaid tweed pattern, the Wrayburn Plaid Tweed Wool Ivy Cap is a great new flat cap styled in the English tradition by Baskerville Hat Company. Its wooly plaid tweed pattern features beige, brown, black and rust hues for a timeless fall and winter look. Finished with a rounded single snap bill, the…

(2)
$34.95

…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)
$18.72

…Ivy Cap by Bailey! Featuring an oversized plaid pattern in a variety of hues, this cap is crafted of two panels with a slightly extended sewn bill and a wooden Bailey side pin. Keep warm while looking great with the new Kottler Wool Blend Ivy Cap!    Approx. 10 1/4" Length, Flat 10" Width, Flat 2…

(2)
$45.00
Available Colors:
  • HUNTERGREEN
  • OLIVEGREEN

…Brixton "B" pin at the back. Ideal for autumn and winter, the Hooligan Tweed Wool Blend Ivy Cap will top off your cool-weather wardrobe perfectly.    Approx. 10 1/4" Length, Flat 9 3/4" Width, Flat 1 1/2" Snap Bill/Brim (Measured from size M cap)   Made of: 90% Polyester 10% Wool    Classic Hooligan…

$28.50

…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

  The Jaxon Square Bill Herringbone Ivy Cap is one sleek-looking cap. Complete with a double snap bill and comfortable quilted lining, this flat cap does not disappoint! Made of a wool blend, the Square Bill Herringbone Ivy Cap is great for fall or winter - pair it with your favorite coat for a…

(31)
$28.95
Available Colors:
  • BROWN
  • CHARCOAL

Caps. Featuring a classic plaid pattern in a medium-weight wool blend fabric, this ivy cap boasts a fleece-lined earflap that may tucked into the cap when not in use. Great to have on-hand on crisp winter days, this cap keeps you warm and offers versatility.   Approx. 10" Length, Flat 10"…

(2)
$93.75
Available Colors:
  • BLACK

…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

…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…

$54.40

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)
$110.00
Available Colors:
  • CHOCOLATEBROWN
  • BLACK

  Combining the looks of their popular Galaxy & Spitfire designs, the new Kangol Hawker Wool Newsboy Cap offers the best of both worlds. Its full, Spitfire-inspired crown is seamless and features implied eight-quarter segments, rather than the classically sewn 8-panels traditionally seen in…

$51.00

…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

…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

…for all seasons — warm enough for winter but not too stifling for summer wear. Cut and sewn into a classic ivy cap style, Simon is finished with a classic rounded single snap bill and quilted satin lining.    Approx. 9 5/8" Length, Flat 10 1/2" Width, Flat 1 3/4" Single Snap Bill/Brim (Measured…

$34.95
Available Colors:
  • BLACK

winter. Featuring a heavier wool and cashmere blend for extra warmth, this cap is finished with a stylish ivy cap design, Wigens pin and quilted satin lining. Fall in love with this style's European design and feel the hand-crafted difference!    Approx. 10" Length, Flat 10" Width, Flat 1…

$80.00
Available Colors:
  • CHARCOAL

  Featuring an eight-panel hybrid newsboy/ivy cap design, the Houndstooth Leather Bill Driver Cap is part of New Era's eclectic EK Collection of hats and caps. Made of a lightweight wool blend, this style boasts a classic houndstooth pattern, New Era flag logo side pin and a breathable cotton…

$50.00

…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

…Jaxon Corduroy Ivy Cap is an excellent 5-point flat cap made of 100% cotton and finished with a smooth satin lining. Complete with a removable Jaxon side pin and a comfortable grosgrain ribbon sweatband, the Jaxon Corduroy Ivy Cap is a great addition to your fall and winter wardrobe.  Approx.…

(25)
$24.95
Available Colors:
  • BLACK
  • BROWN

  A cute layered flower makes the Betmar Lydia Wool Blend Cap a must have for both autumn and winter! This adorable flat cap puts the fun into functional! Keep your head warm without losing an ounce of style. Approx. 4" Crown, 8-Panel 2 1/4" Curved Bill/Brim   Made of:  55%…

$44.00

  Add a little sparkle to dreary fall and winter days with the Lucerne Wool Cap by Betmar! Featuring a lightweight wool and metallic thread blend, Lucerne boasts a gentle sparkle and is finished with a side bow adorned with faux pearl accents. Its soft and packable body folds and crushes for…

$40.00
Available Colors:
  • BLACK
  • BERRY
  • CHARCOAL

  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

…waxed cotton into the new fall/winter collection. The Jaxon Wax Cotton Ivy Cap will last in performance, style and comfort. The treated lightweight cotton ivy cap is the perfect accessory to protect you from the winter rain drops that come your way.   Approx. 2" Snap Bill   …

(44)
$24.95
Available Colors:
  • BLACK
  • BROWN

…with a single-snap bill 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   Classic Ivy Cap Design Classic Houndstooth Pattern Single Snap Bill Grosgrain…

(4)
$34.95

  Flat Cap Club Style   Crafted of incredibly lightweight wool fabric, the Lightweight Wool Newsboy Cap is part of Baskerville Hat Company's newest Fall/Winter line. The handsome Italian charcoal wool fabric features light gray heathering for added texture that beautifully compliments…

$34.95
Available Colors:
  • CHARCOAL

…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

…cotton sweatband. Perfect for keeping the old dome covered and toasty warm this fall and winter, the Goat Leather Newsboy Cap is sure to become your go-to cap of the season!    Approx. 10 1/4" Length, Flat 2 1/8" Extended Sewn Bill   Made of: 100% Goat Leather   Classic…

(2)
$90.00
Available Colors:
  • SADDLE

…ivy cap features an elasticized sweatband, a sewn brim/bill and an embroidered Jaxon "J" at its back. Offered in three great basic colors, the Jaxon Kid's Wool Ivy Cap easily compliments any outfit.    Style your little one to the nines with the Jaxon Kid's Wool Ivy Cap!   …

$28.00

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