Our vintage women’s hats offer the perfect balance of nostalgic silhouettes, sleek design, and modern convenience. This curated selection of women’s cloche hats, flapper hats, sun hats, and other retro options was designed with your comfort and head coverage needs in mind. Adding timeless chic to any wardrobe, our vintage hats for sale will satisfy even the most romantic of old-school souls.
  1. Elizabeth Hats
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    Elizabeth Hats
    Our Price $34.99
  2. Distressed Rosette Beanie Hat - All Cotton
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    Distressed Rosette Beanie Hat - All Cotton
    Retail $45.00 Our Price $29.99
  3. Cardani Cuddle Cloche Hat | Viscose from Bamboo Hat for Women
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    Cardani Cuddle Cloche Hat | Viscose from Bamboo Hat for Women
    Retail $42.99 Our Price $26.99
  4. Flapper Turban | Vintage Flapper Hat in Soft Viscose from Bamboo by Cardani
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    Flapper Turban | Vintage Flapper Hat in Soft Viscose from Bamboo by Cardani
    Retail $40.00 Our Price $24.99
  5. Tatum Triple Braid Sun Hat
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    Tatum Triple Braid Sun Hat
    Retail $55.00 Our Price $34.99
  6. Bondi Burlap Cloche Hat
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    Bondi Burlap Cloche Hat
    Retail $35.99 Our Price $22.99
  7. Ombre Zuri Sun Hat
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    Ombre Zuri Sun Hat
    Retail $41.99 Our Price $28.99
  8. Presley Ribbon Cloche | Summer Hats for Women
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    Presley Ribbon Cloche | Summer Hats for Women
    Retail $39.99 Our Price $25.99
  9. Large Flapper Turban | Cardani® Viscose from Bamboo Hat for Large Heads
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    Large Flapper Turban | Cardani® Viscose from Bamboo Hat for Large Heads
    Retail $40.00 Our Price $24.99
  10. Lauren UPF Visor Hat | Cardani 100% Cotton Hats | Aloe Vera Liner | UPF 50+ Sun Protection
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    Lauren UPF Visor Hat | Cardani 100% Cotton Hats | Aloe Vera Liner | UPF 50+ Sun Protection
    Retail $50.00 Our Price $29.99
  11. Cardani Buttery Soft Cupro Flapper Turban
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    Cardani Buttery Soft Cupro Flapper Turban
    Retail $40.00 Our Price $24.99
  12. Beaded Knit Turban for Women
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    Beaded Knit Turban for Women
    Retail $29.99 Our Price $19.99
  13. Bejeweled Knit Turban for Women | Embellished Turbans for Fall & Winter
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    Bejeweled Knit Turban for Women | Embellished Turbans for Fall & Winter
    Retail $35.99 Our Price $24.99
  14. Uma Newsboy Cap | Asymmetrical Fall & Winter Hat for Women
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    Uma Newsboy Cap | Asymmetrical Fall & Winter Hat for Women
    Retail $48.99 Our Price $29.99
  15. Petite Fit Pillbox Floral Cap | Lambswool Pull On Hat
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    Petite Fit Pillbox Floral Cap | Lambswool Pull On Hat
    Retail $39.99 Our Price $24.99
  16. Wool Alani Cloche Hat | Fall & Winter Hats for Women
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    Wool Alani Cloche Hat | Fall & Winter Hats for Women
    Retail $39.99 Our Price $25.99
  17. Wool Kennie Cloche Hat
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    Wool Kennie Cloche Hat
    Retail $42.99 Our Price $29.99
  18. Uptown Slouchy Hat | Embellished 100% Organic Cotton Newsboy Cap
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    Uptown Slouchy Hat | Embellished 100% Organic Cotton Newsboy Cap
    Retail $55.00 Our Price $34.99
  19. Bow Tie Sun Hat | Cardani Sun Protection UPF 50+ | 100% Cotton Hats with Aloe Vera Lining
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    Bow Tie Sun Hat | Cardani Sun Protection UPF 50+ | 100% Cotton Hats with Aloe Vera Lining
    Retail $50.00 Our Price $29.99
  20. Rose Garden Cloche Hat | Summer Hats for Women
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    Rose Garden Cloche Hat | Summer Hats for Women
    Retail $52.98 Our Price $25.99
  21. Pop of Color Bucket Hat | Summer Hats for Women
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    Pop of Color Bucket Hat | Summer Hats for Women
    Retail $52.98 Our Price $25.99
  22. Violet Flapper Hat | Vintage UPF 50+ Hat | 100% Cotton with Aloe Vera Lining
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    Violet Flapper Hat | Vintage UPF 50+ Hat | 100% Cotton with Aloe Vera Lining
    Retail $50.00 Our Price $29.99
  23. Gianna Wool Cloche Hat | Warm Winter Hats for Women
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    Gianna Wool Cloche Hat | Warm Winter Hats for Women
    Retail $45.00 Our Price $29.99
  24. Vintage Cora Wool Cloche Hat | Winter Hats for Women
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    Vintage Cora Wool Cloche Hat | Winter Hats for Women
    Retail $45.00 Our Price $29.99
  25. Quinn Wool Cloche Hat | Winter Hats for Women
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    Quinn Wool Cloche Hat | Winter Hats for Women
    Retail $45.00 Our Price $29.99
  26. Fleece Leona Cloche Hat | Vintage Winter Hats
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    Fleece Leona Cloche Hat | Vintage Winter Hats
    Retail $28.00 Our Price $14.99
  27. Wool Sophie Cloche | Winter Hats for Women
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    Wool Sophie Cloche | Winter Hats for Women
    Retail $85.00 Our Price $49.99
  28. Wool Felt Bowler Hat | Stylish Winter Hats for Women
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    Wool Felt Bowler Hat | Stylish Winter Hats for Women
    Retail $55.00 Our Price $35.99
  29. Aurora Polar Fleece Cloche Hat | Winter Hats for Women
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    Aurora Polar Fleece Cloche Hat | Winter Hats for Women
    Retail $20.00 Our Price $19.99
  30. Cheetah Bow Cloche Hat | Winter Hats for Women
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    Cheetah Bow Cloche Hat | Winter Hats for Women
    Our Price $45.99
  31. Dakota Hat | Winter Wool Hats for Women
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    Dakota Hat | Winter Wool Hats for Women
    Retail $75.00 Our Price $42.99
  32. Charlie Cloche Hat | Winter Hats for Women
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    Charlie Cloche Hat | Winter Hats for Women
    Retail $80.00 Our Price $45.99
  33. Wool Joanna Brimmed Hat | Wool Winter Hats for Women
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    Wool Joanna Brimmed Hat | Wool Winter Hats for Women
    Retail $70.00 Our Price $44.99
  34. Wool Juniper Rose Cloche Hat | Winter Hats for Women
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    Wool Juniper Rose Cloche Hat | Winter Hats for Women
    Retail $70.00 Our Price $46.99
  35. Cotton Roller Hat | All Cotton Hats for Women
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    Cotton Roller Hat | All Cotton Hats for Women
    Retail $38.99 Our Price $28.99

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Vintage Women’s Hats from Headcovers

There’s something almost stately about vintage ladies’ hats, harkening back to a time when putting together an outfit was seen as necessity, rather than as a hobby exclusively reserved for fashionistas. At Headcovers, we have a soft spot for 1920s ladies’ hats, from turbans to cloches and wide-brimmed sun hats. The key to pulling off a vintage ladies’ hat is pairing it with a dash of mystique - knowing, as we do, that true style is timeless.

 

What is a Cloche?

The word cloche literally means “bell” in French, which makes sense, because cloche hats are defined by their bell-shaped silhouette and barely-there brim. Designed to be worn low over the eyes, cloches simultaneously say “come hither” and “stay back, I’m fabulous” - protecting the wearer while being irresistibly chic. Cloches are perhaps best known as the quintessential flapper hat, chosen by the chicest members of that long-ago decade.

For cancer patients or people experiencing hair loss, our 1920s cloche hats offer full head coverage. Our winter and summer cloche hat options will keep your retro style looking fresh all year round. Choose an asymmetrical version for extra pizazz, worn cocked at a slight angle for an authentic vintage attitude.

 

How to Style a Cloche Hat

The truth is that a 1920’s cloche hat doesn’t look quite right next to sweatpants and a hoodie. Still, with just the slightest amount of effort, cloches can look quite natural matched with pieces you already own. Try a pair of dark jeans with clean lines, and a shirt with a bit of embellishment or an interesting neck detail. Pretty prints and rich colors look good when topped with a cloche. Any pair of well-made shoes will do, but lace-up loafers, ballet slippers, and knee-high boots look especially good with this sort of hat. 

The key is to think poise - go with a knee-or-calf-length skirt instead of a mini, favoring straight lines instead of flared. A pair of dangly earrings works wonders to frame your face, and a string pearls probably wouldn’t hurt, either.

 

Other Vintage Ladies’ Hats We Love

The 1920s was a golden era of hats. Influenced largely by the flamboyant turn-of-the-century styles, wide-brimmed garden hats kicked off the decade as the most popular thing to wear. Often tied with a bow and accented with artificial flowers, women wore these pleasing toppers for an afternoon in the town or to share a kettle of tea. Try our Tatum Triple Braid Sun Hat for a fashionable base, building up the look with a Hand Crocheted Sunflower Pin or a vibrant Sassy Band for an authentic touch.

Halfway through the decade, the turban spiked in popularity due to a fascination with the exotic far east. Women often wore these twisted strips of fabric accessorized with a dose of bling; get a similar look with our Bejeweled Knit Turban or the sparkly Yasmin Twist Turban. If a whiff of nature is more your style, try the classic Flapper Turban, popular with our customers for being soft and stylish all at once.

 

Is a Vintage Hat Right for Me?

The word “vintage” can sometimes intimidate people, especially if they usually associate vintage women’s hats with dusty wardrobes or faded black-and-white photos. However, to appreciate vintage style one must only have a curiosity about the past and an appreciation for one-of-a-kind elegance. The great thing about vintage style is that it gives you an edge above rest, lets you climb to the next level of sophistication, shows that you have an eye for timeless beauty. If you’re a daydreamer, a book reader, a tea drinker, a museum-goer, or a lover of life, then you’ll enjoy perusing our vintage hats for sale. 

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