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Vintage Women's Headpieces and Hats

Historically an indicator of social status, the hat in all its shapes has long been the ultimate style distinguisher and its fashion legacy carries on to date. In the early 1800s, women opted for eccentric bonnets with feathers, flowers and ribbons which in the 1920s had evolved into neater head-hugging hats with more movement-friendly embellishments. The styles of hats that have emerged since are very diverse in style and purpose – below we have untangled the most significant types of hats over the decades to help you in your search for the perfect vintage headpiece. 


The beret hat is a soft round cap, traditionally made from woollen felt, with a bulging flat crown and a tight-fitting brimless headband. The style is highly associated with France, the military and early 1900’s school uniforms. 

Cloche hat 

As the name suggests, the cloche hat is a bell-shaped ladies hat with a more or less accentuated cap. Popular in the 1920s, the style was embraced by the public through iconic artist performers like Josephine Baker. 


Probably the most coveted hat style, the fedora hat got its name from Victorien Sardou’s cross-dresser play Fedora and became a symbol of the women’s rights movement. In the 1920s the style became popular also amongst men and has since enjoyed a consistent revive through icons like Indiana Jones, Frank Sinatra and Johnny Depp. 

Pillbox hat 

A pillbox hat is a small women’s hat with a flat crown, straight, upright sides, and no brim. It is named after the small cylindrical cases that pills used to be sold in and influenced by military headgear. The pillbox is much associated with the 1960s and was the hat of choice of First Lady Jackie O.

OFV says: With a special penchant for dressy vintage hats, our edit of pre-owned designer and vintage headpieces span decades of iconic hats crafted by some of the most prominent hatters, milliners and fashion houses in history. So whether you’re on the lookout for a Panama-style straw hat for the beach; an eye-catching ostrich hat for the Royal Ascot; or a Hermès silk turban to tackle a bad hair day, our edit of sensational one-off vintage hats will top off both casual and formal looks, whatever the occasion.

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Prada Leather Vitello Drive Bowler Handbag

508.5000 Label 1 : Womens Accessories > Womens Hats Metal / Material : Leather Length (inches) : 15.00 Style Keyword : Womens Hats Depth (inches) : 14.00 Gender : Female Width (inches) : 29.00 Mens/Womens : Womens Accessories : Hats specification : Black, ,

Louis Vuitton Boite Chapeaux 30 Rondes Hat Box Monogram M23626

417259.0000 Label 1 : Womens Accessories > Womens Hats Metal / Material : Leather Style Keyword : Womens Hats Gender : Female Mens/Womens : Womens Accessories : Hats specification : Brown, , Size : W 30.0 x H 17.0 x D 28.0 cm

Louis Vuitton Porto Monet Chapeau Coin Purse Dot Infinity M91570

111779.0000 Label 1 : Womens Accessories > Womens Hats Metal / Material : Leather Style Keyword : Womens Hats Gender : Female Mens/Womens : Womens Accessories : Hats specification : Red, , Excellent Size : W 10.5 x H 10.0 x D 2.0 cm Chain length. 27.0 cm

Jean Paul Gaultier 1990s rabbit-felt red vintage fedora hat

Chic wine-red rabbit-felt fedora hat by Jean Paul Gaultier from the 1990s

Sharon 1960s hare fur black vintage hat

Dressy hare fur hat by Sharon Originals from the 1960s

Vintage 1970s pearl skull cap

A charming 1970's pearl cage skull cap, perfect for a vintage bride

Christian Dior 1970s red vintage Bowler hat

1973 Christian Dior vintage Rabbit hair bowler hat

Vintage 1960s Velvet & jet Toque style black Hat

Fabulous signed Jan Leslie late 50's early 60's Black velvet high hat with jet beading to front

Vintage 1940's veiled tilt yellow hat

1940's Jean Arlett Yellow sculpted felt tilt hat with original dotted veiling

Vintage 1930s woven & corded straw black day hat

An unusual woven straw hat dating from the 1930's with a dipped widows peak

Vintage 1930's German velvet cocktail black hat

A soft black silk velvet cocktail hat with original net & original sterling silver pin

Vintage 1960s velvet & veiled red hat

1960s red velvet vintage hat with veil

Jacoll 1960s wool felt red vintage hat

Red Felt Hat with Blue Over stitching by Jacoll

Harvey Nichols 1970s black ribbon & Straw vintage Hat

Chic Vintage Straw Hat with Ribbon Detail by Harvey Nichols

Vintage 1920s Chiffon purple Cloche Hat

Fine lilac chiffon 1920s cloche hat with fabric flowers on the side

Vintage 1930s Wool Felt green Cloche hat

1930s olive green 100% wool felt cloche with bronze sequin swirl decoration all over

Roberta Bernaya 1940s Italian Velvet Skull Cap Black Vintage Hat

Original Roberta Bernaya 1940's Italian black velvet skull cap with rhinestone curls at side

Vintage 1920s Feather Nude Hat

1920s blush / nude feather cap with triple structural feather flower on back

Vintage 1940s Topper with Roses Pink Hat

1940s Rosalia Masin taupe felt topper with pink rose detail