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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

Bob Mackie FW 1988 Old Hollywood Themed Nightlife Velvet Embellished Jacket US 8
Bob Mackie FW 1988 Old Hollywood Themed Nightlife Velvet Embellished Jacket US 8

Bob Mackie FW 1988 Old Hollywood Themed Nightlife Velvet Embellished Jacket US 8

By Bob Mackie

Located in Montgomery, TX

The imagery transforms the jacket into a wearable map of glamorous old Los Angeles: the iconic Brown Derby hat, Cocoanut Grove palm trees, crescent moons, stars, stylized portraiture...

Category

1980s North American Vintage Derby Hats

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

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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Agnes B. Vintage 1990s Black Lambskin Leather Fedora Hat, Size 56

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By AGNES B.

Located in Moreno Valley, CA

Agnes B Fedora Black Leather Hat . Lambskin Leather Fedora Hat. Vintage 1990s Black Leather Traditional 1920s / 30s New York Style Fedora Hat Hand crafted A leather fedora hat with a...

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Late 20th Century French Vintage Derby Hats

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Lanvin Alber Elbaz Black Sun Hat Navy Ribbon Band, 2006

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By Lanvin Paris

Located in Boca Raton, FL

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1960s Oleg Cassini Navy Blue + White Mod Linen + Silk Nautical Vintage 60s Hat
1960s Oleg Cassini Navy Blue + White Mod Linen + Silk Nautical Vintage 60s Hat

1960s Oleg Cassini Navy Blue + White Mod Linen + Silk Nautical Vintage 60s Hat

By Oleg Cassini

Located in San Diego, CA

Beyond chic 1960s OLEG CASSINI navy blue and white linen and silk blend nautical hat! The white section features a linen and silk blend that retains its' shape nicely. Navy blue faux...

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1960s French Vintage Derby Hats

1950s Alex Callifornia Black Straw Cocktail Hat w Stiff Netting Flourish
1950s Alex Callifornia Black Straw Cocktail Hat w Stiff Netting Flourish

1950s Alex Callifornia Black Straw Cocktail Hat w Stiff Netting Flourish

Located in Gresham, OR

A fabulous 1950s Alex California black straw hat woven in a beautiful pattern (see closeup pic) embellished with a whorl of stiff black horsehair netting for drama! So chic!

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Bollman Co. Ivory Boho Greenwich Floppy Hat with Ostrich Feather Band – M, 1970s
Bollman Co. Ivory Boho Greenwich Floppy Hat with Ostrich Feather Band – M, 1970s

Bollman Co. Ivory Boho Greenwich Floppy Hat with Ostrich Feather Band – M, 1970s

By Bollman Hat Company

Located in Tucson, AZ

Started in 1868, the Bollman Hat Company is America's oldest hat maker and still provides luxury millinery products for brands like Helen Kaminski. Made of soft doeskin wool in wardr...

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1970s American Vintage Derby Hats

Vintage 1940s Black Straw Percher Hat Tilt Hat Millinery
Vintage 1940s Black Straw Percher Hat Tilt Hat Millinery

Vintage 1940s Black Straw Percher Hat Tilt Hat Millinery

Located in Nashville, TN

This statement 1940's straw percher hat, rendered in a tightly woven black straw, set off by scalloped knotted straw details along the brim, is a rare piece to behold. The wonderfu...

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1940s Vintage Derby Hats

Christian Dior brown hat
Christian Dior brown hat

Christian Dior brown hat

By John Galliano for Christian Dior, Christian Dior

Located in SAINT-OUEN-SUR-SEINE, FR

DIOR - (Made in France) Brown rabbit hat topped with a wide corduroy ribbon. A Collection circa 2000 under the artistic direction of John Galliano. Condition: Very good condition D...

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Early 2000s French Vintage Derby Hats

1930 Lilly Dache Paris Black Spiral Horsehair Ribbon Picture Hat & Wire Brim
1930 Lilly Dache Paris Black Spiral Horsehair Ribbon Picture Hat & Wire Brim

1930 Lilly Dache Paris Black Spiral Horsehair Ribbon Picture Hat & Wire Brim

By Lilly Daché

Located in Gresham, OR

1930s Lilly Dache - Paris black horsehair spiral ribbon cloche hat with wide wired brim. Fits down low and close to the head for a sculpted silhouette. Brim is extravagant and unusua...

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1930s American Vintage Derby Hats

1930s Florence Reichman New Look-Inspired Black Felt Hat w/ Peaked Brim
1930s Florence Reichman New Look-Inspired Black Felt Hat w/ Peaked Brim

1930s Florence Reichman New Look-Inspired Black Felt Hat w/ Peaked Brim

Located in Gresham, OR

A 1950s Florence Reichman New Look-inspired black felt hat with peaks at sides and back. Size Medium. Aerodynamic cocktail charm!

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1950s American Vintage Derby Hats

Yves Saint Laurent hat by Yves Saint Laurent circa 1990
Yves Saint Laurent hat by Yves Saint Laurent circa 1990

Yves Saint Laurent hat by Yves Saint Laurent circa 1990

By Yves Saint Laurent

Located in SAINT-OUEN-SUR-SEINE, FR

YVES SAINT LAURENT - A ready-to-wear Collection circa 1990 under the artistic direction of Yves Saint Laurent. Braided coral-red straw hat decorated with a black ribbon. Made in Fr...

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Vivienne Westwood Worlds End Black Wool Felt Mountain Hat
Vivienne Westwood Worlds End Black Wool Felt Mountain Hat

Vivienne Westwood Worlds End Black Wool Felt Mountain Hat

By Vivienne Westwood

Located in Scottsdale, AZ

Vivienne Westwood Worlds End Black Wool Felt Mountain Hat is a striking statement piece that embodies the designer’s signature punk-inspired aesthetic with a modern twist. Crafted fr...

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21st Century and Contemporary Vintage Derby Hats

1960s Irene Of New York Fuchsia Straw Pillbox Hat W/ Large Bow At Back
1960s Irene Of New York Fuchsia Straw Pillbox Hat W/ Large Bow At Back

1960s Irene Of New York Fuchsia Straw Pillbox Hat W/ Large Bow At Back

By Irene, Irene of New York

Located in Gresham, OR

As gorgeous Irene of New York tightly woven fuchsia straw pillbox that is adorned at the back with a large stiffly-structured straw bow. More than mod!

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1960s American Vintage Derby Hats

Yves Saint Laurent Rare Mondrian Color Block Helmet Hat YSL, 1965
Yves Saint Laurent Rare Mondrian Color Block Helmet Hat YSL, 1965

Yves Saint Laurent Rare Mondrian Color Block Helmet Hat YSL, 1965

By Yves Saint Laurent

Located in Boca Raton, FL

The Mondrian collection is one of the most iconic historical fashion moments brought forth by designer, Yves Saint Laurent. This collection gave way to a new and constantly reemergin...

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1960s Unknown Vintage Derby Hats

1970 Yves Saint Laurent Black Fur Felt Molded Hat w/ LONG Lacquered Feather
1970 Yves Saint Laurent Black Fur Felt Molded Hat w/ LONG Lacquered Feather

1970 Yves Saint Laurent Black Fur Felt Molded Hat w/ LONG Lacquered Feather

By Yves Saint Laurent

Located in Gresham, OR

Early 1970s rare Yves Saint Laurent plush fine wool high-crown hat, molded shape with rolled soft edge and one singular extra-long stiffly lacquered pheasant feather. Fits M-L crown.

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1970s French Vintage Derby Hats

1950s Irina Roublon Silk Floral Trim Black Straw Hat W/ Velvet Ribbons
1950s Irina Roublon Silk Floral Trim Black Straw Hat W/ Velvet Ribbons

1950s Irina Roublon Silk Floral Trim Black Straw Hat W/ Velvet Ribbons

By Irina Roublon

Located in Gresham, OR

This superb couture 1950s Irina Roublon multi-color, silk floral trimmed hat is a hand-made beauty. Multiple layers of lacquered black veiling make up the body with a soft-peaked cro...

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1950s American Vintage Derby Hats

Anthony Peto hat
Anthony Peto hat

Anthony Peto hat

Located in SAINT-OUEN-SUR-SEINE, FR

ANTHONY PETO - Brown and beige wool felt hat. Condition: Very good condition Dimensions: Length: 56 cm SKU:CHP75

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Late 20th Century Vintage Derby Hats

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Robert Rodriguez Silk Dress with Large Flower

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By Robert Rodriguez

Located in Water Mill, NY

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Located in Berlin, BE

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John Galliano black twill evening dress with floral feather appliqués, fw 2005
John Galliano black twill evening dress with floral feather appliqués, fw 2005

John Galliano black twill evening dress with floral feather appliqués, fw 2005

By John Galliano

Located in London, GB

▪ John Galliano archival evening dress ▪ Fall-Winter 2005 ▪ Constructed from black acetate-viscose twill ▪ Silk flower stem shaped inserts ▪ Organza and tulle floral appliqués ▪ De...

Category

Early 2000s 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.