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Vintage Derby Hats

Red  Straw Black Bow Derby Hat Vintage 1960s
Red  Straw Black Bow Derby Hat Vintage 1960s

Red Straw Black Bow Derby Hat Vintage 1960s

Located in Wallkill, NY

Red Mod Straw Black Bow Derby Hat Vintage 1960s \. Large Crown with an Oversized Black Patent Bow.

Category

1960s Unknown Vintage Derby Hats

felt derby hat
felt derby hat

felt derby hat

Located in SAINT-OUEN-SUR-SEINE, FR

UNKNOWN - Moleskin rabbit felt 'derby' style hat with brown leather inside and topped with a large-grain bow ribbon.

Category

1950s Vintage Derby Hats

1960s Christian Dior Black Felt Derby Hat
1960s Christian Dior Black Felt Derby Hat

1960s Christian Dior Black Felt Derby Hat

By Christian Dior

Located in Scottsdale, AZ

The Perfect Winter Hat Has Arrived! Circa 1960s, this Dior derby style hat features a porkpie brim.

Category

1960s Italian Vintage Derby Hats

1960s Yves Saint Laurent Ivory and Navy Derby Hat Patent Leather Orange Hatband
1960s Yves Saint Laurent Ivory and Navy Derby Hat Patent Leather Orange Hatband

1960s Yves Saint Laurent Ivory and Navy Derby Hat Patent Leather Orange Hatband

By Yves Saint Laurent

Located in Boca Raton, FL

Borrowing its aesthetic from the classic men’s derby hat, this 1960s Yves Saint Laurent ivory hat is sure to add unparalleled style to any dressed-up or dressed-down look.

Category

1960s French Vintage Derby Hats

Vintage Bowler / Derby Hat Bottle Opener in Heavy Solid Gilded Brass, 70s
Vintage Bowler / Derby Hat Bottle Opener in Heavy Solid Gilded Brass, 70s

Vintage Bowler / Derby Hat Bottle Opener in Heavy Solid Gilded Brass, 70s

Located in Roma, IT

Originally designed in mid-19th-century London by the Bowler brothers to protect gamekeepers from low-hanging branches while on horseback, the Derby hat (or Bowler hat) later became ...

Category

Mid-20th Century Italian Mid-Century Modern Vintage Derby Hats

Materials

Metal, Brass, Chrome

1980s Amen Wardy Rhinestone Bow Hat
1980s Amen Wardy Rhinestone Bow Hat

1980s Amen Wardy Rhinestone Bow Hat

By Amen Wardy

Located in Scottsdale, AZ

The Most Adorable 80s Hat Is Here! Made of black Wool, this wide brim derby hat features a unique slit in the brim and crown and is decorated with a rhinestone bow.

Category

1980s Unknown Vintage Derby Hats

David Gil for Bennington Potters Man's Face Ceramic Sculpture on Base
David Gil for Bennington Potters Man's Face Ceramic Sculpture on Base

David Gil for Bennington Potters Man's Face Ceramic Sculpture on Base

By David Gil, Bennington Potters

Located in Brooklyn, NY

Features a ceramic face and derby hat with round mirrored glass eyes mounted on a steel rod set into cast stone.

Category

1960s American Mid-Century Modern Vintage Derby Hats

Materials

Cast Stone, Steel

Charlie Chaplin Pullstring Flat Puppet
Charlie Chaplin Pullstring Flat Puppet

Charlie Chaplin Pullstring Flat Puppet

Located in Bradenton, FL

Chaplin recalled how the costume induced the character, so that 'by the time I walked on to the stage he was fully born'. The derby hat, the cane, the bow-tie and close-trimmed moust...

Category

Late 20th Century American Vintage Derby Hats

Materials

Wood

Vintage Equestrian Riding Helmet Bottle Opener in Silver Plated Brass Metal 70s
Vintage Equestrian Riding Helmet Bottle Opener in Silver Plated Brass Metal 70s

Vintage Equestrian Riding Helmet Bottle Opener in Silver Plated Brass Metal 70s

Located in Roma, IT

This sculptural Mid-20th-Century Modern bottle opener was found in Italy and purchased by us together with two similar pieces, each shaped like a different style of hat: one a Bowler...

Category

Mid-20th Century Italian Mid-Century Modern Vintage Derby Hats

Materials

Metal, Silver Plate, Brass

CAST PARTY Signed Lithograph 1988, Art Deco Portrait Confetti, Broadway Show
CAST PARTY Signed Lithograph 1988, Art Deco Portrait Confetti, Broadway Show

CAST PARTY Signed Lithograph 1988, Art Deco Portrait Confetti, Broadway Show

By Robin Morris

Located in Union City, NJ

CAST CLUB is a zany modern portrait of five androgynous looking characters dressed in black tuxedos, sporting bold purple derby hats and bow ties, theatrical makeup, pouty pink lips,...

Category

1980s Art Deco Vintage Derby Hats

Materials

Lithograph

STREET SCENE Signed Hand Drawn Lithograph 1980, Figurative Expressionism
STREET SCENE Signed Hand Drawn Lithograph 1980, Figurative Expressionism

STREET SCENE Signed Hand Drawn Lithograph 1980, Figurative Expressionism

By Lester Johnson

Located in Union City, NJ

In STREET SCENE depicts a group of mannequin-like men and women walking as they look upward and sideways - not at each other, drawn in an expressive watercolor style, posed crowded t...

Category

1980s Contemporary Vintage Derby Hats

Materials

Lithograph

Navy Floral Silk *Large Size* Sailor Collar Luncheon Trumpet Dress – L, 1960s
Navy Floral Silk *Large Size* Sailor Collar Luncheon Trumpet Dress – L, 1960s

Navy Floral Silk *Large Size* Sailor Collar Luncheon Trumpet Dress – L, 1960s

Located in Tucson, AZ

In light-as-air floral silk, this ladylike dress begs to be worn to a shoreline lunch or to the Derby with a perky hat. A charming mix of modesty and femininity, it glides over the b...

Category

1960s Unknown Vintage Derby Hats

Recent Sales

Vintage Hermès French Equestrian Race 100% Silk Scarf Print Jacket FR 38/ US 4 6
Vintage Hermès French Equestrian Race 100% Silk Scarf Print Jacket FR 38/ US 4 6

Vintage Hermès French Equestrian Race 100% Silk Scarf Print Jacket FR 38/ US 4 6

By Hermès

Located in Ormond Beach, FL

An eccentric & vibrant jacket that would look gorgeous paired with a big, elegant floppy hat (Kentucky Derby style), mini skirt & stiletto heels.

Category

1990s French Vintage Derby Hats

Chanel
Chanel

Chanel

Sold

Size: 1

Chanel

By Chanel

Located in Los Angeles, CA

Black derby hat with ethnic embroidery stitch in heavy wool yarns.

Category

1980s French Vintage Derby Hats

Man with Bowler Hat Sculpture by Bennington Potters
Man with Bowler Hat Sculpture by Bennington Potters

Man with Bowler Hat Sculpture by Bennington Potters

By Bennington Potters, David Gil

Located in Phoenix, AZ

Features a white ceramic face and derby hat with round mirrored glass eyes mounted on a steel rod and stand.

Category

1970s American Mid-Century Modern Vintage Derby Hats

Materials

Steel

Two Antique Iron Hatter's Molds with Leather Inserts
Two Antique Iron Hatter's Molds with Leather Inserts

Two Antique Iron Hatter's Molds with Leather Inserts

Located in Astoria, NY

Two antique hat forms; a Derby (Bowler) and a Boater, in iron with original leather inserts.

Category

20th Century American Vintage Derby Hats

Materials

Iron

1960s Kates Canada Mink Fur Trim Derby Hat
1960s Kates Canada Mink Fur Trim Derby Hat

1960s Kates Canada Mink Fur Trim Derby Hat

Located in Scottsdale, AZ

The Perfect Hat For Your Wardrobe! Circa 1960s by Boutique Kates Canada, this derby style hat is black wool with a black mink fur brim trim.

Category

1960s Canadian Vintage Derby Hats

Mr King Plush 2-Tone Camel Beaver Fur Parker Bowles Bowler Derby Hat - S, 1974
Mr King Plush 2-Tone Camel Beaver Fur Parker Bowles Bowler Derby Hat - S, 1974

Mr King Plush 2-Tone Camel Beaver Fur Parker Bowles Bowler Derby Hat - S, 1974

Located in Tucson, AZ

Like Fedoras, bowler hats look particularly good on women because of their typically masculine association. This one takes androgyny a step further by combining an oversized crown, g...

Category

1970s American Vintage Derby Hats

C.1960 Henry Pollak Mod Black Mohair Hat With White Leather Trim
C.1960 Henry Pollak Mod Black Mohair Hat With White Leather Trim

C.1960 Henry Pollak Mod Black Mohair Hat With White Leather Trim

By Henry Pollak

Located in Atlanta, GA

The shape and style is reminiscent of a classic derby hat with a black mohair body and white leather trim at the brim.

Category

1960s American Vintage Derby Hats

Yves Saint Laurent YSL Soft Blue Silk Hat, 1970s
Yves Saint Laurent YSL Soft Blue Silk Hat, 1970s

Yves Saint Laurent YSL Soft Blue Silk Hat, 1970s

By Yves Saint Laurent

Located in Boca Raton, FL

From fezzes to wide brim derby hats, Saint Laurent runways during the early decades were rife with a variety of colorful headwear.

Category

1970s Vintage Derby Hats

Straw Derby Style Tilt Hat, 1940's
Straw Derby Style Tilt Hat, 1940's

Straw Derby Style Tilt Hat, 1940's

Sold

Size: 22 (Please See Description)

Straw Derby Style Tilt Hat, 1940's

Located in Atlanta, GA

This 1940's hat could not decide whether to be a trilby or a derby so it took the best elements of both and created a menswear style look for a ladies straw topper.

Category

1940s French Vintage Derby Hats

1970s Yves Saint Laurent Hat with Pearl and Stud Trim
1970s Yves Saint Laurent Hat with Pearl and Stud Trim

1970s Yves Saint Laurent Hat with Pearl and Stud Trim

By Yves Saint Laurent

Located in Scottsdale, AZ

1970s YVES SAINT LAURENT derby style hat made of ivory wool velour. The high crown is circled w/a grosgrain ribbon band trimmed w/brass studs and dangling simulated pearls.

Category

1970s French Vintage Derby Hats

CAST PARTY Signed Lithograph, Modern Portrait, Theater Party Broadway Show
CAST PARTY Signed Lithograph, Modern Portrait, Theater Party Broadway Show

CAST PARTY Signed Lithograph, Modern Portrait, Theater Party Broadway Show

By Robin Morris

Located in Union City, NJ

CAST CLUB is a zany modern portrait of five androgynous looking characters dressed in black tuxedoes, sporting bold purple derby hats and bow ties, theatrical makeup, pouty pink lips...

Category

1980s Art Deco Vintage Derby Hats

Materials

Lithograph

NY Street Scene I, Signed Lithograph, Crowd Portrait, Expressionist Line Drawing
NY Street Scene I, Signed Lithograph, Crowd Portrait, Expressionist Line Drawing

NY Street Scene I, Signed Lithograph, Crowd Portrait, Expressionist Line Drawing

By Lester Johnson

Located in Union City, NJ

Both male and female figures stand crowded together-their hair textures, round eyeglass frames, derby hats, and bent arm poses create a dynamic 1980's New York City scene.

Category

1970s Contemporary Vintage Derby Hats

Materials

Lithograph

NY STREET SCENE I Signed Lithograph, City Crowd Portrait, Black Line Drawing
NY STREET SCENE I Signed Lithograph, City Crowd Portrait, Black Line Drawing

NY STREET SCENE I Signed Lithograph, City Crowd Portrait, Black Line Drawing

By Lester Johnson

Located in Union City, NJ

Both male and female figures stand crowded together; their hair textures, round eyeglass frames, derby hats, and bent arm positions create a dynamic 1980's New York City scene.

Category

1970s Contemporary Vintage Derby Hats

Materials

Lithograph

STREET SCENE Signed Lithograph, City People Portrait, Figurative Expressionism
STREET SCENE Signed Lithograph, City People Portrait, Figurative Expressionism

STREET SCENE Signed Lithograph, City People Portrait, Figurative Expressionism

By Lester Johnson

Located in Union City, NJ

In STREET SCENE a group of mannequin like male and female figures are looking upward and sideways - not at each other, drawn in an expressive watercolor style, posed crowded together...

Category

1980s Contemporary Vintage Derby Hats

Materials

Lithograph

NY STREET SCENE II Hand Drawn Lithograph, Women Walking, Group Portrait, Faces
NY STREET SCENE II Hand Drawn Lithograph, Women Walking, Group Portrait, Faces

NY STREET SCENE II Hand Drawn Lithograph, Women Walking, Group Portrait, Faces

By Lester Johnson

Located in Union City, NJ

Both male and female figures stand crowded together moving - one woman wearing slacks and high heels, man in a derby hat, bent arms, legs and man's arm on the composition's right edg...

Category

1970s Contemporary Vintage Derby Hats

Materials

Lithograph

John Cavanagh Bowler Hat in Original Box
John Cavanagh Bowler Hat in Original Box

John Cavanagh Bowler Hat in Original Box

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H 5 in W 9.5 in D 11 in

John Cavanagh Bowler Hat in Original Box

By John Cavanaugh

Located in Los Angeles, CA

Beautifully styled Cavanaugh Riding Derby / Bowler hat in Original box - a handsome accessory for the room or ready for every day use - tally ho!

Category

20th Century Vintage Derby Hats

Materials

Felt, Leather

New Orleans Jazz & Heritage Festival 1976 Poster
New Orleans Jazz & Heritage Festival 1976 Poster

New Orleans Jazz & Heritage Festival 1976 Poster

Located in San Francisco, CA

The image is of Fats Houston, the definitive grand marshal of the Eureka marching jazz band. With his signature derby hat in one hand and woven straw fan in the other, he was the...

Category

1970s American Vintage Derby Hats

Vintage Makins White & Cream Straw & Feather Statement Derby Church Hat
Vintage Makins White & Cream Straw & Feather Statement Derby Church Hat

Vintage Makins White & Cream Straw & Feather Statement Derby Church Hat

Located in Portland, OR

This lovely unique, dramatic vintage hat is from Makins New York. The hat is made of coated white straw, cream feathers and rhinestones. This wide brim, high angled hat has beautiful...

Category

1980s American Vintage Derby Hats

1970s Wine Felt Derby With Hatpin and Veil
1970s Wine Felt Derby With Hatpin and Veil

1970s Wine Felt Derby With Hatpin and Veil

Located in San Francisco, CA

1970s wine colored felt derby with an enlarged decorative hatpin, a grosgrain band, and a veil that theres in the back finished with a 6-inch drape.

Category

1970s Vintage Derby Hats

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Will Steinman New Look Pink Blue Strapless Back Bow Ballerina Dress - XS, 1950s
Will Steinman New Look Pink Blue Strapless Back Bow Ballerina Dress - XS, 1950s

Will Steinman New Look Pink Blue Strapless Back Bow Ballerina Dress - XS, 1950s

By Will Steinman

Located in Tucson, AZ

Pure spun-sugar perfection, right down to the cotton candy colors. Visible beneath the silver lattice-embroidered top skirt, the ruffled attached petticoat provides volume enough to ...

Category

1950s American Vintage Derby Hats

1996Jean Paul Gaultier Velvet Gown with Large Fabric Beads
1996Jean Paul Gaultier Velvet Gown with Large Fabric Beads

1996Jean Paul Gaultier Velvet Gown with Large Fabric Beads

By Jean Paul Gaultier

Located in Austin, TX

1996 Jean Paul Gaultier maroon velvet evening gown with long straps and extra large fabric covered beads - 6 1/2" L x 1 1/4" W. 29" bust, 32" waist, 32.5" hips, 59" length. Co...

Category

1990s Italian Vintage Derby Hats

Avant Guard 2000’s Cherry Red Mongolian Lamb Fitted Jacket & Skirt Suit - Alpaca
Avant Guard 2000’s Cherry Red Mongolian Lamb Fitted Jacket & Skirt Suit - Alpaca

Avant Guard 2000’s Cherry Red Mongolian Lamb Fitted Jacket & Skirt Suit - Alpaca

Located in Sheffield, GB

Avant Guard 2000’s Cherry Red Mongolian Lamb Fitted Jacket & Skirt Suit by La Belle Histoire, crafted from Alpaca Wool with jacquard satin lining and beautiful nacré buttons. The Qua...

Category

Early 2000s European Vintage Derby Hats

Dolce & Gabbana Lace up Silk Dress
Dolce & Gabbana Lace up Silk Dress

Dolce & Gabbana Lace up Silk Dress

By Dolce & Gabbana

Located in Water Mill, NY

A beautiful silk dress in a pink and green geometric print from Dolce & Gabbana. The bodice is vertically boned, fitted through to the hips and has an attached matching pink adjusta...

Category

1990s Italian Vintage Derby Hats

Jean Paul Gaultier black one shoulder gown with attached pouch
Jean Paul Gaultier black one shoulder gown with attached pouch

Jean Paul Gaultier black one shoulder gown with attached pouch

By Jean Paul Gaultier

Located in Austin, TX

Jean Paul Gaultier black one shoulder gown with attached pouch 100% rayon 31" bust, 26" waist, 25" hips, 66" length Condition: Excellent size S / US4 / IT40

Category

1990s Unknown Vintage Derby Hats

F/W 1998 Givenchy by Alexander McQueen Runway Sheer Black Lace Blue Stretch Gown
F/W 1998 Givenchy by Alexander McQueen Runway Sheer Black Lace Blue Stretch Gown

F/W 1998 Givenchy by Alexander McQueen Runway Sheer Black Lace Blue Stretch Gown

By Givenchy, Alexander McQueen

Located in West Hollywood, CA

From Alexander McQueen's Fall/Winter 1998 "Blade Runner" collection for Givenchy, this sheer black lace gown features striking a blue underlay. Inspired by the retro-futuristic costu...

Category

1990s French Vintage Derby Hats

F/W 1993 Karl Lagerfeld Dark Green Backless Halter Point Hem Chiffon Dress
F/W 1993 Karl Lagerfeld Dark Green Backless Halter Point Hem Chiffon Dress

F/W 1993 Karl Lagerfeld Dark Green Backless Halter Point Hem Chiffon Dress

By Karl Lagerfeld

Located in West Hollywood, CA

This incredible deep green dress by Karl Lagerfeld is from the Fall/Winter 1993 collection and features an intricate skirt design featured heavily on the season's runway. This ultra-...

Category

1990s French Vintage Derby Hats

Robert Rodriguez Silk Dress with Large Flower
Robert Rodriguez Silk Dress with Large Flower

Robert Rodriguez Silk Dress with Large Flower

By Robert Rodriguez

Located in Water Mill, NY

A fabulous mint green silk dress by Robert Rodriguez. It has spaghetti straps and lots of diagonal seaming leading to a large petal flower comprising most of the skirt front. It has...

Category

Early 2000s American Vintage Derby Hats

Prada F/W 2012 Geometric Print Crystal & Plexi Embellished Belted Jacket
Prada F/W 2012 Geometric Print Crystal & Plexi Embellished Belted Jacket

Prada F/W 2012 Geometric Print Crystal & Plexi Embellished Belted Jacket

By Miuccia Prada, Prada

Located in Boca Raton, FL

Muccia Prada, the visionary behind the Italian house of Prada, is known for her subversive approach to fashion. She famously introduced the use of nylon to high fashion in the 1990s,...

Category

2010s Italian Vintage Derby Hats

ALEXANDER McQUEEN A/W 2007 "Witches" Black Red Silk Taffeta Bubble Evening Gown
ALEXANDER McQUEEN A/W 2007 "Witches" Black Red Silk Taffeta Bubble Evening Gown

ALEXANDER McQUEEN A/W 2007 "Witches" Black Red Silk Taffeta Bubble Evening Gown

By Alexander McQueen

Located in Thiensville, WI

Brand / Manufacturer: Alexander McQueen Collection: A/W 2007 "Witches" Designer: Alexander McQueen Style: Evening Gown Color(s): Shades of black, red Lined: Yes Marked Fabric Cont...

Category

Early 2000s Italian Vintage Derby Hats

Roberto Cavalli Blue & White Ming Gown Dress with Fur Trim Wrap S/S 2005 Sz 42IT
Roberto Cavalli Blue & White Ming Gown Dress with Fur Trim Wrap S/S 2005 Sz 42IT

Roberto Cavalli Blue & White Ming Gown Dress with Fur Trim Wrap S/S 2005 Sz 42IT

By Roberto Cavalli

Located in Saint Petersburg, FL

Roberto Cavalli Vintage Blue & White Ming Gown Dress with Fur Trim Wrap S/S 2005 Sz 42IT. This dress is marked a 42IT. Measurements not stretched reflect a small but has a lot of s...

Category

Early 2000s Italian Vintage Derby Hats

Vintage turquoise beaded silk sheer floral layered wedding slip dress gown M L
Vintage turquoise beaded silk sheer floral layered wedding slip dress gown M L

Vintage turquoise beaded silk sheer floral layered wedding slip dress gown M L

Located in Milano, Lombardia

LOVE LALI VINTAGE A breathtaking vintage gown. I would estimate this to be from around the late 90's. It has a pale blue lining which is overlayed with a sheer turquoise layer that ...

Category

1990s Vintage Derby Hats

Alexander McQueen FW 2002 Black Silk Blouse Top Jacket
Alexander McQueen FW 2002 Black Silk Blouse Top Jacket

Alexander McQueen FW 2002 Black Silk Blouse Top Jacket

By Alexander McQueen

Located in Berlin, BE

In the captivating language of Alexander McQueen's FW 2002 "Supercalifragilistic" Collection, this jacket or blouse is a poetic embodiment of elegance and drama. Its sleek black Silk...

Category

Early 2000s Italian Vintage Derby Hats

Vintage 1990s black and white wool suit  Moschino Cheap & Chic
Vintage 1990s black and white wool suit  Moschino Cheap & Chic

Vintage 1990s black and white wool suit Moschino Cheap & Chic

By Moschino

Located in LAGNY-SUR-MARNE, FR

Vintage 1990s black and white suit (jacket and skirt) by Moschino Cheap & Chic. The black and red version of this suit can be seen on the ICONIC Fran fine on the hit sitcom the Nanny...

Category

1990s Italian Vintage Derby Hats

Dior 30 Montaigne Bar Jacket Off-White Ecru Plumetis Tulle Skirt Set FR38
Dior 30 Montaigne Bar Jacket Off-White Ecru Plumetis Tulle Skirt Set FR38

Dior 30 Montaigne Bar Jacket Off-White Ecru Plumetis Tulle Skirt Set FR38

By Christian Dior

Located in Jersey City, NJ

The 30 Montaigne Bar jacket and plumetis tulle skirt represent the most iconic ensemble in the history of Dior - a timeless symbol of femininity, structure, and grace. First introduc...

Category

2010s French Vintage Derby Hats

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Vintage Derby Hats For Sale on 1stDibs

There is a broad range of vintage derby hats for sale on 1stDibs. Our collection of vintage derby hats includes a variety of colors, spanning black, brown, white and more. If you’re looking for accessories from a specific time period, our collection is diverse and broad-ranging, and you’ll find some that date back to the 20th Century while other versions may have been produced as recently as the 20th Century. Vintage derby hats designed by Amen Wardy, Christian Dior and Yves Saint Laurent — each of whom created beautiful versions of these treasured items — are worth considering.

How Much are Vintage Derby Hats?

Prices for vintage derby hats can differ depending upon size, time period and other attributes — on 1stDibs, these accessories begin at $125 and can go as high as $1,200, while these items, on average, fetch $498.