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Winter Hats

  • Talese Harris Tweed Wool Baseball Cap - Stetson Hat Cap Stetson Hats
    Talese Harris Tweed Wool Baseball Cap - Stetson Hat Cap Stetson Hats STW366-GREY Grey OSFM
    Save 16%
    $ 54.00
    $ 45.45
    Stetson Hats

    Talese Harris Tweed Wool Baseball Cap - Stetson Hat

    Baseball cap made with legendary handwoven Harris tweed wool. Rounded crown. Bound brim, 2.5" Paisley print lining. Decorative strap in back with S...

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    $ 54.00
    $ 45.45
    Save 16%
  • Edison Weathered Leather Newsboy Cap, Large - Stetson Hat Flat Cap Stetson Hats
    Edison Weathered Leather Newsboy Cap, Large - Stetson Hat Flat Cap Stetson Hats STW199-BLK3 Black Large
    $ 62.00
    Stetson Hats

    Edison Weathered Leather Newsboy Cap, Large - Stetson Hat

    Weathered leather newsboy cap by the Legendary Stetson Hats. The worn look takes you back in time to the newsboys of the busy New York streets. Eig...

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    $ 62.00
  • Waldo Corduroy Ivy Cap with Print Lining - Stetson Hat Flat Cap Stetson Hats
    Waldo Corduroy Ivy Cap with Print Lining - Stetson Hat Flat Cap Stetson Hats STW370 Taupe Medium
    Sold out
    $ 22.50
    Stetson Hats

    Waldo Corduroy Ivy Cap with Print Lining - Stetson Hat

    Corduroy men's flat cap for fall weather. Plaid lining. 1.5" sewn bill with contrast color underbrim. Embroidered STETSON® lettering detail. 15% ny...

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    $ 22.50
  • Cleveland Wool Felt Raw Edge Fedora up to 2XL - Stacy Adams Hats Safari Hat Stacy Adams Hats SAW536-BLK2 Black Medium (22.5")
    Cleveland Wool Felt Raw Edge Fedora up to 2XL - Stacy Adams Hats Safari Hat Stacy Adams Hats SAW536-GREY2 Grey Medium (22.5")
    $ 64.25
    Stacy Adams Hats

    Cleveland Wool Felt Raw Edge Fedora up to 2XL - Stacy Adams Hats

    Wool felt fedora hat with feather accent. Raw edge 2.5" wide brim. 19-Ligne grosgrain band with side bow. Signature STACY ADAMS pin detail Dented a...

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    $ 64.25
  • Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats Gambler Hat Stacy Adams Hats
    Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats Gambler Hat Stacy Adams Hats SAW509 Black Large (23")
    Save 30%
    $ 64.25
    $ 44.95
    Stacy Adams Hats

    Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats

    Wool felt porkpie rocker hat with feather detail. Bound 2" wide brim. 16-Ligne grosgrain ribbon band with side bow. Leather inner band. Satin linin...

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    $ 64.25
    $ 44.95
    Save 30%
  • Satipo Wool Felt Fedora Hat with Raw Edge, up to 2XL - Indiana Jones Hat Fedora Hat Indiana Jones Hats
    Satipo Wool Felt Fedora Hat with Raw Edge, up to 2XL - Indiana Jones Hat Fedora Hat Indiana Jones Hats IJ551-BRN1 Brown Small (54.5 cm)
    $ 69.00
    Indiana Jones Hats

    Satipo Wool Felt Fedora Hat with Raw Edge, up to 2XL - Indiana Jones Hat

    Indiana Jones Satipo fedora hat. Structured C-crown and pinched front. Raw edge 2.5" wide brim. Grosgrain band with side bow and Indiana Jones pin....

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    $ 69.00
  • Tucson Crushable Water Repellent Wool Felt Outback Hat - Scala Hat Safari Hat Scala Hats DF185-KAKI2 Khaki Medium (57 cm)
    $ 60.00
    Scala Hats

    Tucson Crushable Water Repellent Wool Felt Outback Hat - Scala Hat

    Classic outback style wool felt hat. Packable, crushable. Naturally water repellent and sun protective. Pinched front and C-crown. Gently curved br...

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    $ 60.00
  • Raider Small Heads Felt Fedora Hat - Indiana Jones Hat Fedora Hat Indiana Jones Hats
    Raider Small Heads Felt Fedora Hat - Indiana Jones Hat Fedora Hat Indiana Jones Hats 551B-BRN Brown Jr. Small (52 cm)
    $ 52.00
    Indiana Jones Hats

    Raider Small Heads Felt Fedora Hat - Indiana Jones Hat

    Indiana Jones Raiders of the Lost Ark fedora hat for small head sizes. Crushable wool felt fedora hat with C-crown and pinched front. Bound 3" wide...

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    $ 52.00
  • Up Brim Ladies Rain Hat - Scala Collezione Hat Kettle Brim Hat Scala Hats LW750-KH Khaki OS
    Up Brim Ladies Rain Hat - Scala Collezione Hat Kettle Brim Hat Scala Hats
    $ 23.00
    Scala Hats

    Up Brim Ladies Rain Hat - Scala Collezione Hat

    Stylish up turned brim breton style rain hat. Scala collection best selling up brim hat style now made of water repellent polyester.   Dimensional ...

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    $ 23.00
  • Crushable Water Repellent Wool Felt Ascot Cap, up to 2XL - Scala Hat Flat Cap Scala Hats
    Crushable Water Repellent Wool Felt Ascot Cap, up to 2XL - Scala Hat Flat Cap Scala Hats DF5-BLK3 Black Large
    $ 44.99
    Scala Hats

    Crushable Water Repellent Wool Felt Ascot Cap, up to 2XL - Scala Hat

    Classic molded wool felt ascot cap. Round, 1.75" padded bill. Packable. Wool felt is naturally sun protective and water repellent. 100% wool felt hat.

    $ 44.99
  • Finlay Felt Hat with Bound Wide Brim - Stacy Adams Hat Safari Hat Stacy Adams Hats
    Finlay Felt Hat with Bound Wide Brim - Stacy Adams Hat Safari Hat Stacy Adams Hats SAW706 Black Medium (22.5")
    $ 69.00
    Stacy Adams Hats

    Finlay Felt Hat with Bound Wide Brim - Stacy Adams Hat

    Wool felt safari style winter hat. Blanket bound 3.25" wide brim. Narrow ribbon tie. Dented and pinched front fedora-like crown. 100% wool felt hat

    $ 69.00
  • Woodstock Distressed Wool Felt Safari Winter Hat - Scala Hat Safari Hat Scala Hats
    Woodstock Distressed Wool Felt Safari Winter Hat - Scala Hat Safari Hat Scala Hats
    $ 59.75
    Scala Hats

    Woodstock Distressed Wool Felt Safari Winter Hat - Scala Hat

    Brown wool felt safari hat with turned up brim. Distressed worn edges.  Fedora-like dented and pinched crown. Wide brim, 3.5" with curled up edge. ...

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    $ 59.75
  • Arizona Distressed Wool Felt Safari Hat - Scala Hats Safari Hat Scala Hats
    Arizona Distressed Wool Felt Safari Hat - Scala Hats Safari Hat Scala Hats LF276-TAN Tan
    $ 68.99
    Scala Hats

    Arizona Distressed Wool Felt Safari Hat - Scala Hats

    Light tan color wool felt safari hat with turned up brim. Distress brown spotted finish creates a worn look. Fedora-like dented and pinched crown. ...

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    $ 68.99
  • Large Flower Felt Cloche Winter Hat- Scala Hat Cloche Scala Hats
    Large Flower Felt Cloche Winter Hat- Scala Hat Cloche Scala Hats LF265BK Black
    $ 59.99
    Scala Hats

    Large Flower Felt Cloche Winter Hat- Scala Hat

    Carretoo wool felt cloche hat with large felt flower. Dimensional brim, 3" wide. Dome crown. Ribbon inner band with drawstring to adjust fit. 100% ...

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    $ 59.99
  • Wool Felt Cloche with Wide Ribbon Band - Scala Hat Cloche Scala Hats
    Wool Felt Cloche with Wide Ribbon Band - Scala Hat Cloche Scala Hats LF261 Red
    $ 54.00
    Scala Hats

    Wool Felt Cloche with Wide Ribbon Band - Scala Hat

    Katie Ann wool felt cloche hat. Dimensional brim, 2.5" wide. Double, stitched ribbon band pulled through crown. Dome crown. Ribbon inner band with ...

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    $ 54.00
  • Scarsdale Structured Wool Felt Raw Edge Fedora up to 2XL - Scala Hats Safari Hat Scala Hats
    Scarsdale Structured Wool Felt Raw Edge Fedora up to 2XL - Scala Hats Safari Hat Scala Hats WF536 Black Medium (22.5")
    $ 59.00
    Scala Hats

    Scarsdale Structured Wool Felt Raw Edge Fedora up to 2XL - Scala Hats

    Structured wool felt safari style hat. Raw edge 2.5" wide brim. 19-Ligne grosgrain band with side bow. SCALA pin and feather detail. Dented and pin...

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    $ 59.00
  • Authentic Basque French Wool Beret - Heritage Par Laulhere Beanie Laulhere
    Authentic Basque French Wool Beret - Heritage Par Laulhere Beanie Laulhere 51-BLK1 Black Small (55 cm)
    Save 46%
    $ 89.00
    $ 47.65
    Laulhere

    Authentic Basque French Wool Beret - Heritage Par Laulhere

    This beautiful French military beret was made by the iconic Heritage par Laulhere company. Beret is approximately 10" diameter with top tassel, cab...

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    $ 89.00
    $ 47.65
    Save 46%
  • Water Repellent Poplin Bucket Rain Hat - Stetson Hats Bucket Hat Stetson Hats
    Water Repellent Poplin Bucket Rain Hat - Stetson Hats Bucket Hat Stetson Hats STW381BK2 Black Medium (22 1/2")
    $ 31.00
    Stetson Hats

    Water Repellent Poplin Bucket Rain Hat - Stetson Hats

    A classic bucket hat made of water repellent poplin. Downward brim, 2.25" wide with stitching detail. Double mesh grommets on sides with STETSON en...

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    $ 31.00
  • Water Repellent Cotton Blend Rain Flat Cap up to 2XL - Stetson Hat Flat Cap Stetson Hats
    Water Repellent Cotton Blend Rain Flat Cap up to 2XL - Stetson Hat Flat Cap Stetson Hats STC60-KAKI2 Khaki Medium (22.5")
    $ 30.00
    Stetson Hats

    Water Repellent Cotton Blend Rain Flat Cap up to 2XL - Stetson Hat

    Classic flat cap style made of water repellent cotton blend fabric. 2" sewn bill. Stetson pin detail. Satin lined crown with STETSON stamp. Soft in...

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    $ 30.00
  • Houndstooth Lined Flat Cap - Dorfman Pacific Hat Flat Cap Dorfman Hat Co. MW204 Brown Small/Medium
    Houndstooth Lined Flat Cap - Dorfman Pacific Hat Flat Cap Dorfman Hat Co. MW204 Grey Small/Medium
    $ 19.00
    Dorfman Hat Co.

    Houndstooth Lined Flat Cap - Dorfman Pacific Hat

    Lightweight flat cap for fall wear. Houndstooth pattern. Snap peak, 1.5". Satin lined crown. Cotton inner band with elasticized front portion. 100%...

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    $ 19.00
  • Petite Size Fashion Felt Capeline Hat - Scala Kids Wide Brim Hat Scala Hats CW220 Black XXS (20")
    $ 22.00
    Scala Hats

    Petite Size Fashion Felt Capeline Hat - Scala Kids

    Classic capeline style hat for small heads. Dome crown. Flat ribbon bound brim, 3" wide (not floppy). Grosgrain ribbon band with loop. Extra-small ...

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    $ 22.00
  • Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats Cloche Callanan Hats
    Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats Cloche Callanan Hats LV424-GREY Grey Medium (57 cm)
    Save 37%
    $ 62.00
    $ 39.00
    Callanan Hats

    Structured Brim Cloche with Big Flower Accent - John Callanan Handmade Hats

    A true 1920's cloche hat. Narrow structured brim on front and side. 1.5" wide downward sloping brim in back. Felt flower petal accent with contrast...

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    $ 62.00
    $ 39.00
    Save 37%
  • Autumn Leaf Cloche Felt Hat - John Callanan Handmade Hats Cloche Callanan Hats LV404 Charcoal Medium (57 cm)
    Autumn Leaf Cloche Felt Hat - John Callanan Handmade Hats Cloche Callanan Hats LV404 Red Medium (57 cm)
    Save 64%
    $ 42.00
    $ 15.00
    Callanan Hats

    Autumn Leaf Cloche Felt Hat - John Callanan Handmade Hats

    Stylish wool felt wide brim cloche hat designed by British milliner, John Callanan. Asymmetrical brim, 3.5" wide. Brim stiffened and curled up on r...

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    $ 42.00
    $ 15.00
    Save 64%
  • Crushable Wool Felt Fedora Hat with Tie Print Band - Stacy Adams Fedora Hat Stacy Adams Hats SAW627bns Brown S/M
    Save 64%
    $ 42.00
    $ 15.00
    Stacy Adams Hats

    Crushable Wool Felt Fedora Hat with Tie Print Band - Stacy Adams

    Brown wool felt fedora hat with feather accent. Dented crown with pinched front. 1.5" wide bounded snap brim. Blue tie print band with Stacy Adams ...

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    $ 42.00
    $ 15.00
    Save 64%
  • Crushable Water Repellent Wool Felt Outback Hat - Scala Hat Safari Hat Scala Hats
    Crushable Water Repellent Wool Felt Outback Hat - Scala Hat Safari Hat Scala Hats
    $ 62.00
    Scala Hats

    Crushable Water Repellent Wool Felt Outback Hat - Scala Hat

    Classic outback style wool felt hat. Packable, crushable. Naturally water repellent. Pinched front and C-crown. Gently curved brim, 3" wide. Ribbon...

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    $ 62.00
  • Packable Water Repellent Wool Felt Outback Hat, Small to 3XL - Scala Hats Safari Hat Scala Hats
    Packable Water Repellent Wool Felt Outback Hat, Small to 3XL - Scala Hats Safari Hat Scala Hats DF6BLK1 Black Small (56 cm)
    $ 68.00
    Scala Hats

    Packable Water Repellent Wool Felt Outback Hat, Small to 3XL - Scala Hats

    Classic wool felt outback hat with feather accent. Packable, crushable. Naturally water repellent. Pinched front and C-crown. Gently curved brim, 3...

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    $ 68.00
  • Studded Asymmetrical Brim Wool Felt Cloche - Callanan Hats Cloche Callanan Hats
    Studded Asymmetrical Brim Wool Felt Cloche - Callanan Hats Cloche Callanan Hats LV449 Black Medium (57 cm)
    Save 34%
    $ 59.25
    $ 39.00
    Callanan Hats

    Studded Asymmetrical Brim Wool Felt Cloche - Callanan Hats

    Katie Ann wool felt cloche hat designed by John Callanan. Circular felt strip detail with studs. Asymmetrical brim, 2.75" wide, turned up on left s...

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    $ 59.25
    $ 39.00
    Save 34%
  • Wool Felt Safari Hat with Scottish Tweed Trim - Adora® Hats Safari Hat Adora Hats
    Wool Felt Safari Hat with Scottish Tweed Trim - Adora® Hats Safari Hat Adora Hats AD1121B Pecan Medium (57 cm)
    $ 51.00
    Adora Hats

    Wool Felt Safari Hat with Scottish Tweed Trim - Adora® Hats

    Wool felt safari hat dented and pinched crown. Grosgrain ribbon trimmed brim, 3" wide. Scottish tweed brim. Grosgrain ribbon band with side bow. In...

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    $ 51.00
  • Wool Felt Safari Hat with Suede Chin Strap - Adora® Hats Safari Hat Adora Hats AD1134A Black Medium (57 cm)
    Wool Felt Safari Hat with Suede Chin Strap - Adora® Hats Safari Hat Adora Hats AD1134B Tan Medium (57 cm)
    $ 52.25
    Adora Hats

    Wool Felt Safari Hat with Suede Chin Strap - Adora® Hats

    Safari wool felt hat with dented and pinched crown. Multitone woven band. Faux suede chin strap. Underwelt brim, 3.75" wide. Inner drawstring to ad...

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    $ 52.25
  • Wool Felt Cloche Hat with Embroidered Sequin Band - Adora® Hats Cloche Adora Hats AD980bn Brown
    Wool Felt Cloche Hat with Embroidered Sequin Band - Adora® Hats Cloche Adora Hats AD980bk Black
    $ 32.00
    Adora Hats

    Wool Felt Cloche Hat with Embroidered Sequin Band - Adora® Hats

    Bucket shape hat with square crown. Downward asymmetrical brim, 3" wide on front, narrows to 2". Stunning colorful embroidered band with tiny gold ...

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    $ 32.00
  • Winter Cap Knit Wool Hat - Scala Collezione Cap Scala Hats lw693gy Grey Medium (57 cm)
    Winter Cap Knit Wool Hat - Scala Collezione Cap Scala Hats lw693nv Navy Medium (57 cm)
    Save 63%
    $ 16.00
    $ 5.99
    Scala Hats

    Winter Cap Knit Wool Hat - Scala Collezione

    Knit wool blend winter baseball cap for women. Fitted style ball cap with 2.75" curved bill. Round seamless crown. Knit inner band. Packable. One s...

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    $ 16.00
    $ 5.99
    Save 63%
  • Reversible Cotton Bucket Hat with Fleece Lining - DPC Global Bucket Hat Dorfman Hat Co.
    Reversible Cotton Bucket Hat with Fleece Lining - DPC Global Bucket Hat Dorfman Hat Co. mw259m Camo Medium (57 cm)
    Save 38%
    $ 16.00
    $ 9.99
    Dorfman Hat Co.

    Reversible Cotton Bucket Hat with Fleece Lining - DPC Global

    Traditional bucket hat with warm fleece lining.  Stitched brim, 2.25" wide. Double metal eyelets. Reversible. Packable. 100% cotton

    $ 16.00
    $ 9.99
    Save 38%
  • Fleecy Canvas Bucket Hat for Men - Dorfman Hats Bucket Hat Dorfman Hat Co. mw259m Brown Medium (57 cm)
    Save 52%
    $ 21.00
    $ 9.99
    Dorfman Hat Co.

    Fleecy Canvas Bucket Hat for Men - Dorfman Hats

    The perfect winter bucket hat. Lined with warm winter fleece. Heavy cotton duck canvas outer layer. Faux leather bound, stitched brim, 2.5" wide. D...

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    $ 21.00
    $ 9.99
    Save 52%
  • Knitted Wool Blend Cloche with Twisted Bow - DNMC Hats Cloche Boardwalk Style Hats da3169 Camel Medium (57 cm)
    Knitted Wool Blend Cloche with Twisted Bow - DNMC Hats Cloche Boardwalk Style Hats da3169 Wine Medium (57 cm)
    Save 47%
    $ 38.00
    $ 19.99
    Boardwalk Style Hats

    Knitted Wool Blend Cloche with Twisted Bow - DNMC Hats

    Cloche style knitted boiled wool hat. Twisted two tone bow in marled colors Shapeable wire edge brim, 2.5" wide. Pull string with touch fastener un...

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    $ 38.00
    $ 19.99
    Save 47%
  • Quilted Cloche Hat with Bow and Tiny Bead Detail by DNMC Cloche Boardwalk Style Hats da3165 Black Medium (57 cm)
    Quilted Cloche Hat with Bow and Tiny Bead Detail by DNMC Cloche Boardwalk Style Hats da3165 Camel Medium (57 cm)
    Save 50%
    $ 30.00
    $ 15.00
    Boardwalk Style Hats

    Quilted Cloche Hat with Bow and Tiny Bead Detail by DNMC

    Cloche style quilted water repellent hat. Warm fleece lining.  100% cotton down filling. Downward, 2" wide brim Tiny bead accented band tied into b...

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    $ 30.00
    $ 15.00
    Save 50%

Warm winter hat styles to keep you protected from the elements. Flat caps, wool beanies, trapper hats with fleece lining and fur trim. Water repellent winter rain hats. Timeless winter hat styles for the whole family.