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Fall and Winter Hats, Caps and Beanies for Women

2020-2021 Women's Fall and Winter Hat Styles

women's fall and winter wool hats

Be stylish and stay warm this winter season with the latest fashion hat styles. This season's hot styles, the gambler, bolero, and boater made of beautiful merino wool felt. This years bright and pastel colors are in, so we have selected fun colorful beanies, ponytail beanies, french berets, pillbox hats and newsboy caps in a large variety of colors. The timeless classic cloche, fedora, safari and floppy hats are embellished with colorful handmade ribbon rosettes, velvet bands. Soft fleece and faux fur lined trapper and ushanka hats.

  • Faux Fur Bucket Hat - Scala Hats, Bucket Hat - SetarTrading Hats
    Faux Fur Bucket Hat - Scala Hats, Bucket Hat - SetarTrading Hats
    Scala Hats

    Faux Fur Bucket Hat - Scala Hats

    $ 38.00

    Soft faux fur winter hat for women. Shapeable brim, wear it turned down as a bucket hat, or turn up brim. Fully lined. One size, best fit medium to...

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    $ 38.00
  • Soft Wool Pulled Turban Beanie - Scala Hats, Beanie - SetarTrading Hats
    Soft Wool Pulled Turban Beanie - Scala Hats, Beanie - SetarTrading Hats
    Scala Hats

    Soft Wool Pulled Turban Beanie - Scala Hats

    $ 29.00

    Soft boiled wool turban style snug fit beanie. Criss cross pulled crown. Packable. 7" deep. Spot clean. Best fit, medium to large 57-59 cm. 100% wool

    $ 29.00
  • Boiled Wool Cuffed Turban Beanie - Scala Hat, Beanie - SetarTrading Hats
    Boiled Wool Cuffed Turban Beanie - Scala Hat, Beanie - SetarTrading Hats
    Scala Hats

    Boiled Wool Cuffed Turban Beanie - Scala Hat

    $ 25.00

    Small turban style beanie. Soft knit boiled wool. Grey cable knit cuff.  Self flower. One size. 100% boiled wool hat.

    $ 25.00
  • Large Brim Wool Felt Safari Hat Sateen Band - Adora® Hats, Safari Hat - SetarTrading Hats
    Adora Hats

    Large Brim Wool Felt Safari Hat Sateen Band - Adora® Hats

    $ 48.00

    Beautiful safari style wool felt hat. Fedora like dented crown with front pinch. Wide downward sloping wide brim, 4" with underwelt edge. Brim is s...

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    $ 48.00
  • Wool Felt Floppy Hat with Fall Colors Print - Adora®Hats, Floppy Hat - SetarTrading Hats
    Adora Hats

    Wool Felt Floppy Hat with Fall Colors Print - Adora®Hats

    $ 36.00

    Inspired by the beautiful autumn colors. Soft wool felt floppy hat. Classic dome crown with floppy brim.   Self tie. Raw edge brim, 4" wide. Ribbon...

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    $ 36.00
  • Wool Felt Cloche with Pleated Microfiber Band - Adora® Hats, Cloche - SetarTrading Hats
    Wool Felt Cloche with Pleated Microfiber Band - Adora® Hats, Cloche - SetarTrading Hats
    Adora Hats

    Wool Felt Cloche with Pleated Microfiber Band - Adora® Hats

    $ 53.00

    Asymmetrical brim wool felt cloche hat. Bell shape crown with 3.75" brim. Brim is turned up on front, narrows toward back. Pleated microfiber band ...

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    $ 53.00
  • Double Ribbon Band Wool Felt Cloche - Adora® Wool Hat, Cloche - SetarTrading Hats
    Adora Hats

    Double Ribbon Band Wool Felt Cloche - Adora® Wool Hat

    $ 43.00

    Classic dome crown wool felt cloche. Double ribbon pulled through felt loop. Adora pin accent. Inner drawstring to adjust fit. Spot clean. 100% wool

    $ 43.00
  • Bowler Hat with Animal Print Band - Adora® Wool Hats, Bowler Hat - SetarTrading Hats
    Bowler Hat with Animal Print Band - Adora® Wool Hats, Bowler Hat - SetarTrading Hats
    Adora Hats

    Bowler Hat with Animal Print Band - Adora® Wool Hats

    $ 48.00

    Classic bowler derby hat for women. Small turned up brim. Round crown. Pulled animal print band. Satin inner band with drawstring to adjust fit. Sp...

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    $ 48.00
  • Boiled Wool Cloche with Piping Accent - Adora® Wool Hats, Cloche - SetarTrading Hats
    Boiled Wool Cloche with Piping Accent - Adora® Wool Hats, Cloche - SetarTrading Hats
    Adora Hats

    Boiled Wool Cloche with Piping Accent - Adora® Wool Hats

    $ 31.00

    Cozy soft wool cloche hat for cold weather. Flat crown with piping detail. Adora pin detail. Small brim, 2.5" wide. Inner drawstring to reduce size...

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    $ 31.00
  • Rolled Brim Boiled Wool Beanie - Adora® Wool Hats, Beanie - SetarTrading Hats
    Rolled Brim Boiled Wool Beanie - Adora® Wool Hats, Beanie - SetarTrading Hats
    Adora Hats

    Rolled Brim Boiled Wool Beanie - Adora® Wool Hats

    from $ 24.00

    Soft knit boiled wool beanie hat. Round crown with coiled trim. Adora pin detail. Rolled edge. One size, fits up to 57 cm. 100% wool.

    from $ 24.00
  • Soft Boiled Wool Cloche with Flower - Adora® Wool Hats, Cloche - SetarTrading Hats
    Soft Boiled Wool Cloche with Flower - Adora® Wool Hats, Cloche - SetarTrading Hats
    Adora Hats

    Soft Boiled Wool Cloche with Flower - Adora® Wool Hats

    $ 31.00

    Asymmetrical brim cloche hat. Dome crown with self flower accent. Adora pin detail. Brim, 3" to 2" wide. Inner drawstring to reduce size. One size,...

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    $ 31.00
  • Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat®, Cloche - SetarTrading Hats
    Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat®, Cloche - SetarTrading Hats
    Adora Hats

    Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat®

    $ 31.00

    Cute little wool cloche hat. Dome crown with cushioned roll brim. Adora pin detail. Small brim, 2.5" wide. Inner drawstring to reduce size. One siz...

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    $ 31.00
  • Shapeable brim Patterned Soft Wool Bucket Hat - Adora Wool Hat®, Cloche - SetarTrading Hats
    Shapeable brim Patterned Soft Wool Bucket Hat - Adora Wool Hat®, Cloche - SetarTrading Hats
    Adora Hats

    Shapeable brim Patterned Soft Wool Bucket Hat - Adora Wool Hat®

    $ 24.00

    Multi color patterned soft knit wool hat. Small shapeable brim, approximately 2.5" wide. Brim can be turned up partially or all around. Inner band ...

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    $ 24.00
  • Soft Wool Turban Beanie with Pleated Accent - Adora Hat®, Beanie - SetarTrading Hats
    Soft Wool Turban Beanie with Pleated Accent - Adora Hat®, Beanie - SetarTrading Hats
    Adora Hats

    Soft Wool Turban Beanie with Pleated Accent - Adora Hat®

    $ 23.75

    Soft boiled wool cuffed beanie. Turban style snug fit. Pleated wool accent with bead detail. Packable. 7" deep. Spot clean. Best fit, small to medi...

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    $ 23.75
  • Plaid Fedora with Button Accent for Fall - Adora Hats®, Fedora Hat - SetarTrading Hats
    Adora Hats

    Plaid Fedora with Button Accent for Fall - Adora Hats®

    $ 18.00

    Stylish little plaid trilby hat. C-crown with tapered crown tip and slight front pinch. Light to dark brown plaid. Wide self band with button and p...

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    $ 18.00
  • Structured Wool Felt Wide Brim Safari Hat - Scala Hats, Safari Hat - SetarTrading Hats
    Scala Hats

    Structured Wool Felt Wide Brim Safari Hat - Scala Hats

    $ 51.00

    Stiff wide brim safari hat. Underwelt brim, 3" wide. Fedora like dented crown with front pinch, 4". Faux suede band with loop and SCALA pin. Ribbon...

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    $ 51.00
  • Wool Felt Fedora with Wide Ribbon Band - Scala Hats, Safari Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Fedora with Wide Ribbon Band - Scala Hats

    $ 49.00

    Wool felt wide brim fedora. Underwelt, straight brim, 2.5" wide. Dented crown, pinched front, 4" high. Wide grosgrain ribbon band with bow and SCAL...

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    $ 49.00
  • Wool Felt Fedora Hat with Red Satin Lining - Callanan Millinery, Safari Hat - SetarTrading Hats
    Wool Felt Fedora Hat with Red Satin Lining - Callanan Millinery, Safari Hat - SetarTrading Hats
    Callanan Hats

    Wool Felt Fedora Hat with Red Satin Lining - Callanan Millinery

    $ 45.00

    Wool felt wide brim fedora hat. Underwelt, slightly downward brim, 2.5" wide. Dented crown, pinched front, 4" high. Grosgrain ribbon band with uniq...

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    $ 45.00
  • Soft Wool Striped Crown Knit Fedora Hat - Callanan Millinery, Fedora Hat - SetarTrading Hats
    Soft Wool Striped Crown Knit Fedora Hat - Callanan Millinery, Fedora Hat - SetarTrading Hats
    Callanan Hats

    Soft Wool Striped Crown Knit Fedora Hat - Callanan Millinery

    $ 31.00

    Soft wool blend knit fedora hat. Striped dented crown with slight front pinch. Small shapeable brim, 2". Knit inner comfort band. One size, fits up...

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    $ 31.00
  • Boucle Cloche with Dimensional Brim - Dorfman Pacific, Cloche - SetarTrading Hats
    Dorfman Pacific

    Boucle Cloche with Dimensional Brim - Dorfman Pacific

    $ 21.00

    Multitone boucle cloche hat. Asymmetrical brim, 2.5" front, 1.5" back.   Grosgrain ribbon band with bow. Structured dome crown. One size, medium. 1...

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    $ 21.00
  • Fuzzy Knit Brim Cloche Hat - Dorfman Pacific, Cloche - SetarTrading Hats
    Dorfman Pacific

    Fuzzy Knit Brim Cloche Hat - Dorfman Pacific

    $ 21.00

    Two tone mohair-like knit cloche hat. Asymmetrical small brim, 2" front, 1" back. Round seamless crown. Leatherette tie with bow. Ribbon inner band...

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    $ 21.00
  • Knit Chenille Cloche Hat - Scala Hats, Cloche - SetarTrading Hats
    Knit Chenille Cloche Hat - Scala Hats, Cloche - SetarTrading Hats
    Scala Hats

    Knit Chenille Cloche Hat - Scala Hats

    $ 29.00

    Packable cloche hat for fall and winter. Classic bell shape hat with 2.25" brim. Knit chenille hat with shapeable wire edge brim. Signature Scala p...

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    $ 29.00
  • Microfleece Up Brim Winter Breton - John Callanan Hats, Kettle Brim Hat - SetarTrading Hats
    Callanan Hats

    Microfleece Up Brim Winter Breton - John Callanan Hats

    $ 32.00

    Warm double layer microfleece hat for cold winter days. Up turned kettle brim hat. Black fleece with red contrast stitching. Reverse side is solid ...

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    $ 32.00
  • Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Scala Hats

    Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats

    $ 59.75

    Soft, crushable wool felt flat top bolero style hat. Slightly floppy raw edge brim, 3.5" wide. Distressed faux suede band with braided overlay. Fea...

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    $ 59.75
  • Knit Beanie with Braided Band and Button Accent - Jeanne Simmons, Beanie - SetarTrading Hats
    Knit Beanie with Braided Band and Button Accent - Jeanne Simmons, Beanie - SetarTrading Hats
    Jeanne Simmons

    Knit Beanie with Braided Band and Button Accent - Jeanne Simmons

    $ 15.00

    Basket weave knit beanie cap. Rolled edge. Braided leatherette strap secured with two buttons. One size. Fits up to 59 cm. 100% acrylic

    $ 15.00
  • Red and Black Turban Beanie Hat for Petite Heads - Jeanne Simmons, Beanie - SetarTrading Hats
    Jeanne Simmons

    Red and Black Turban Beanie Hat for Petite Heads - Jeanne Simmons

    $ 22.00

    Two tone boiled wool small beanie. Red crown with double black piping around the crown. Accordion detail on side. Small size, 54-56 cm.  100% boile...

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    $ 22.00
  • Knit Cloche Hat with Thin Leatherette Tassel Tie - Jeanne Simmons, Cloche - SetarTrading Hats
    Jeanne Simmons

    Knit Cloche Hat with Thin Leatherette Tassel Tie - Jeanne Simmons

    $ 27.00

    Soft wool blend bucket hat. Contrast inline design band with think faux suede tie with tassels. Downward brim, 2" wide. Ribbon inner band with draw...

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    $ 27.00
  • Chenille Knit Fedora Hat with Cheetah Band - Jeanne Simmons Hats, Fedora Hat - SetarTrading Hats
    Chenille Knit Fedora Hat with Cheetah Band - Jeanne Simmons Hats, Fedora Hat - SetarTrading Hats
    Jeanne Simmons

    Chenille Knit Fedora Hat with Cheetah Band - Jeanne Simmons Hats

    $ 29.00

    Chenille knit women's fedora hat. Dented crown with front pinch. Wide, slightly downward brim, 3" . Faux hair on cheetah band with buckle detail. I...

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    $ 29.00
  • Wool Felt Flat Top Boater Hat - Biltmore Made in USA, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Wool Felt Flat Top Boater Hat - Biltmore Made in USA

    $ 125.00

    Stunning soft wool felt flat top vintage couture hat. Slightly tapered crown sidewalls. Flat brim 2.75" wide. Grosgrain ribbon band with knot and f...

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    $ 125.00
  • Wool Felt Boater Hat with Tassel Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Wool Felt Boater Hat with Tassel Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Boater Hat with Tassel Band - Scala Hats

    $ 59.75

    Soft wool felt flat top bolero style hat. Flat underwelt brim, 3" wide. Faux suede band with metal loop and tassel detail. Scala pin. Satin inner b...

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    $ 59.75
  • Wool Felt Cloche Hat with Velvet Band - Scala Hat, Cloche - SetarTrading Hats
    Callanan Hats

    Wool Felt Cloche Hat with Velvet Band - Scala Hat

    $ 59.25

    Classy asymmetrical brim wool felt cloche hat for winter. Brim is turned up on front, 2.5" wide, tapers to a brimless back. Deep dome crown, like t...

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    $ 59.25
  • Crushable Wool Felt Western Hat with Aztec Band - Scala Hats, Cowboy Hat - SetarTrading Hats
    Scala Hats

    Crushable Wool Felt Western Hat with Aztec Band - Scala Hats

    $ 69.00

    Dark brown wool felt cowboy hat. C-crown with front pinched. Crushable wool felt. Overwelt brim with wire edge to shape to your likem 3.5" wide. Az...

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    $ 69.00
  • Wool Felt Safari Hat with Whip Stitch - Callanan Hats, Safari Hat - SetarTrading Hats
    Callanan Hats

    Wool Felt Safari Hat with Whip Stitch - Callanan Hats

    $ 35.00

    Wool felt safari hat with whip stitch detail. Soft wool felt construction. Underwelt brim, 2.5" wide. Crown is 4" high. One size, medium, 57 cm. Dr...

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    $ 35.00
  • Wool Felt Safari Hat with Braided Suede Band - Scala Hats, Safari Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Safari Hat with Braided Suede Band - Scala Hats

    $ 49.00

    Dark brown wool felt safari hat with pinched crown. Soft wool felt construction with floppy, raw edge brim, 2 3/8" wide. Braided faux suede band. C...

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    $ 49.00
  • Wool Felt Safari Hat with Colorful Beaded Band - Scala Hat, Safari Hat - SetarTrading Hats
    Wool Felt Safari Hat with Colorful Beaded Band - Scala Hat, Safari Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Safari Hat with Colorful Beaded Band - Scala Hat

    $ 60.00

    Black wool felt safari hat. Unique multicolor beaded grosgrain ribbon band with mesh overlay. Underwelt wide brim, 3.5". Fedora-like dented and pin...

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    $ 60.00
  • Wool Felt Safari Hat with Tooled Leatherette Band - Scala Hats, Safari Hat - SetarTrading Hats
    Wool Felt Safari Hat with Tooled Leatherette Band - Scala Hats, Safari Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Safari Hat with Tooled Leatherette Band - Scala Hats

    $ 60.00

    Wool felt safari hat with dented crown and front pinch. Slightly downward sloping soft, but not floppy, raw edge brim, 3" wide. Tooled faux leather...

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    $ 60.00
  • Wool Felt Cattleman Cowboy Hat for Small Heads - Karen Keith Hats, Cowboy Hat - SetarTrading Hats
    Wool Felt Cattleman Cowboy Hat for Small Heads - Karen Keith Hats, Cowboy Hat - SetarTrading Hats
    Great hats by Karen Keith

    Wool Felt Cattleman Cowboy Hat for Small Heads - Karen Keith Hats

    $ 31.00

    Classic cattleman style cowboy in for small head sizes Brown structured (firm) wool felt hat. Narrow ribbon band. Leatherette sweatband. Curled bri...

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    $ 31.00
  • Wool Felt Safari Hat for Small Heads - Kakadu Australia, Safari Hat - SetarTrading Hats
    Wool Felt Safari Hat for Small Heads - Kakadu Australia, Safari Hat - SetarTrading Hats
    Kakadu

    Wool Felt Safari Hat for Small Heads - Kakadu Australia

    $ 68.00

    Small size structured wool felt safari hat with leather band. Pressed teardrop crown with front pinch. Downward sloping raw edge firm brim, 3" wide...

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    $ 68.00
  • Indigo Upcycled Jersey Beanie Hat for Healing - Flipside Hats, Beanie - SetarTrading Hats
    Indigo Upcycled Jersey Beanie Hat for Healing - Flipside Hats, Beanie - SetarTrading Hats
    Flipside Hats

    Indigo Upcycled Jersey Beanie Hat for Healing - Flipside Hats

    $ 39.00

    Made in America with eco-conscious materials. Two tone beanie cap is made from upcycled cotton jersey. Soft, lightweight beanie for all day comfort...

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    $ 39.00
  • Lavender Fleece Winter Cap for Healing - Flipside Hats, Cap - SetarTrading Hats
    Flipside Hats

    Lavender Fleece Winter Cap for Healing - Flipside Hats

    $ 39.00

    Made in America with eco-conscious recycled materials. Super warm winter cap is made from recycled polyester stretch fleece. Soft and lightweight p...

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    $ 39.00
  • Ethereal Organic Cotton Fleece Cap for Healing - Flipside Hats, Cap - SetarTrading Hats
    Flipside Hats

    Ethereal Organic Cotton Fleece Cap for Healing - Flipside Hats

    $ 39.00

    Made in America with eco-conscious materials. This warm cap is made from tencel organic cotton stretch sweatshirt fleece. Soft, lightweight two ton...

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    $ 39.00
  • Petite Striped Crown Knit Fedora Hat - San Diego Hat, Fedora Hat - SetarTrading Hats
    Petite Striped Crown Knit Fedora Hat - San Diego Hat, Fedora Hat - SetarTrading Hats
    San Diego Hat Company

    Petite Striped Crown Knit Fedora Hat - San Diego Hat

    $ 20.00

    Striped crown knit fedora hat for small head sizes. Contrast color knit band and brim edge. Dented crown with pinched front. Brim is 2" wide. Light...

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    $ 20.00
  • Black Floppy Hat with Embroidered Appliques - Brooklyn Hats, Floppy Hat - SetarTrading Hats
    Brooklyn Hat

    Black Floppy Hat with Embroidered Appliques - Brooklyn Hats

    $ 58.00

    Wide brim wool felt black floppy hat. Classic dome crown. Stunning, colorful flower and butterfly appliques. Red satin inner lining. Raw brim, 4" w...

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    $ 58.00
  • Floppy Brim Wool Felt Women's Safari Hat - Brooklyn Hats, Safari Hat - SetarTrading Hats
    Brooklyn Hat

    Floppy Brim Wool Felt Women's Safari Hat - Brooklyn Hats

    $ 50.00

    Wide brim wool felt safari hat with very floppy brim. Classic fedora-like crown with deep front pinch. Grosgrain ribbon band with side feather. Raw...

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    $ 50.00
  • Petite Floppy Brim Wool Felt Safari Hat - Brooklyn Hats, Safari Hat - SetarTrading Hats
    Brooklyn Hat

    Petite Floppy Brim Wool Felt Safari Hat - Brooklyn Hats

    $ 50.00

    Wide brim wool felt safari hat with very floppy brim. Classic fedora-like crown with deep front pinch. Grosgrain ribbon band with side feather. Raw...

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    $ 50.00