20% OFF STOREWIDE

Chicago's Most Trendy Leather Boots

Your cart

Your cart is empty

Continue shopping

Women Vintage Retro Boots

Women Vintage Retro Y2K Trending Brands

Shop by Style

90's Style

Y2K Style

Vintage Cowboy Western

Knee High Style

Platform style

High Heel/ party

Designer / Luxury

Winter/Snow Style

Square Toe Style

Party / Fashion

Our Condition Rating system


We offer a clear, easy-to-understand condition rating to ensure quality on each pair we sell in our new and pre-lovd inventory from "New" "Like New," "Excellent," "Good" condition with a detailed explanation of what each rating means.

New condition

Boots in new condition are either with their original packing or replacement box. No signs of wear on the upper, lining or soles.

Like New Condition

Boots in like new condition shows minimal or no wear on the soles, upper or lining but they were floor display model or shelf pulls.

Excellent Condition

Boots in excellent condition shows minimal wear on the soles, upper or lining. Hardly visible stain. they might be customer returns. Plenty life left.

Good COndition

Boots have been worn but still in good condition. There may be normal signs of wear such heel drag, transfer of color due to misuse storage, light pilling, stains or fading.

Women Vintage Retro Y2K Boots

73 Results

Clear filters
Jeffrey Campbell Women Katlyn Black Suede Leather Retro Vintage 90s Boots size 7

Jeffrey Campbell Women Katlyn Black Suede Leather Retro Vintage 90s Boots size 7

Jeffrey Campbell

$125.00

1 color, 1 size
  • 7
Brian Co Women Green Comfortable Vegan Leather Lightweight Festival Boots sz 7.5

Brian Co Women Green Comfortable Vegan Leather Lightweight Festival Boots sz 7.5

Brian Co

$49.00

1 color, 1 size
  • 7.5
Jeffrey Campbell Women Jerem Vegan Black Leather Retro Square Toe Boots size 9

Jeffrey Campbell Women Jerem Vegan Black Leather Retro Square Toe Boots size 9

Jeffrey Campbell

$79.00

Bed Stu Women Distressed Beige Leather Grounge Moto Biker Tall Boots size 10

Bed Stu Women Distressed Beige Leather Grounge Moto Biker Tall Boots size 10

Bed Stu

$269.00

Skechers Women Camouflage Fabric Vintage 90s Retro Party Festival Boots size 6

Skechers Women Camouflage Fabric Vintage 90s Retro Party Festival Boots size 6

SKECHERS

$59.00

1 color, 1 size
  • 6
Via Spiga Women Retro 90's Pale Pink Suede Wedge Sneaker Boots size 6.5

Via Spiga Women Retro 90's Pale Pink Suede Wedge Sneaker Boots size 6.5

Via Spiga

$79.00

1 color, 1 size
  • 6.5
Timberland Women Winnicut Dark Brown Leather Faux Fur Lined Winter Boots size 8

Timberland Women Winnicut Dark Brown Leather Faux Fur Lined Winter Boots size 8

Timberland

$59.00

1 color, 1 size
  • 8
Skechers Women Faux Fur Cuff Brown Suede Lace up Pom Pom Boots size 10

Skechers Women Faux Fur Cuff Brown Suede Lace up Pom Pom Boots size 10

SKECHERS

$69.00

1 color, 1 size
  • 10
Gian Marco Women Brown Suede Elastic Panel Western Heeled Ankle Boots 7US EUR 37

Gian Marco Women Brown Suede Elastic Panel Western Heeled Ankle Boots 7US EUR 37

Gian Marco

$149.00

1 color, 1 size
  • 7
Free People Wmn Double Stack Y2k 90s Platform Cream Leather Boots 7.5US EUR 38

Free People Wmn Double Stack Y2k 90s Platform Cream Leather Boots 7.5US EUR 38

Free People

$169.00

1 color, 1 size
  • 7.5
Hush Puppies Women Vintage Retro 90's Brown Suede Faux Shearling Boots Size 6.5

Hush Puppies Women Vintage Retro 90's Brown Suede Faux Shearling Boots Size 6.5

Hush Puppies

$49.00

1 color, 1 size
  • 6.5
Enrico Antinori Women Smooth Grey Suede Dressy Mid Calf Round Boots Sz 7US EUR37

Enrico Antinori Women Smooth Grey Suede Dressy Mid Calf Round Boots Sz 7US EUR37

Enrico Antinori

$69.00

1 color, 1 size
  • 7
Stuart Weitzman Women Black Suede Dressy Office Wedge Ankle boots size 9.5

Stuart Weitzman Women Black Suede Dressy Office Wedge Ankle boots size 9.5

Stuart Weitzman

$79.00

1 color, 1 size
  • 9.5
Jeffrey Campbell Wmn FL 90's Vintage Vedette Fabric Lasercut Pointy Boots sz 8

Jeffrey Campbell Wmn FL 90's Vintage Vedette Fabric Lasercut Pointy Boots sz 8

Jeffrey Campbell

$125.00

1 color, 1 size
  • 8
Gentle Souls Women Benton Slit Brown Suede Buckle Ankle Boots size 7.5

Gentle Souls Women Benton Slit Brown Suede Buckle Ankle Boots size 7.5

Gentle Souls

$72.00

1 color, 1 size
  • 7.5
Lita by Ciara Women Italian White Leather Chelsea Mid Boots size 7US EUR38

Lita by Ciara Women Italian White Leather Chelsea Mid Boots size 7US EUR38

Lita by Ciara

$189.00

1 color, 1 size
  • 7
Mephisto Women Rezia Slouch Soft Black Leather Zip Ankle Boots size 10

Mephisto Women Rezia Slouch Soft Black Leather Zip Ankle Boots size 10

Mephisto

$225.00

1 color, 1 size
  • 10
Gentle Souls Women Mona Black Suede lace-up Combat Boots size 7.5

Gentle Souls Women Mona Black Suede lace-up Combat Boots size 7.5

Gentle Souls

$72.00

1 color, 1 size
  • 7.5
Free People Wmn Double Retro 90 Platform Black Patent Leather Boots 9.5US EUR 40

Free People Wmn Double Retro 90 Platform Black Patent Leather Boots 9.5US EUR 40

Free People

$169.00

1 color, 1 size
  • 9.5
Free People Wmn Double Stack Y2k 90s Platform Cream Leather Boots 9.5US EUR 40

Free People Wmn Double Stack Y2k 90s Platform Cream Leather Boots 9.5US EUR 40

Free People

$169.00

1 color, 1 size
  • 9.5
Naturalizer Women Talon Buckle Wide Calf Black Leather Moto Biker Boots Size 7W

Naturalizer Women Talon Buckle Wide Calf Black Leather Moto Biker Boots Size 7W

Naturalizer

$89.00

1 color, 1 size
  • 7W
Sorel Women Joan Of Artic III Lace Cozy Waterproof Wedge Chelsea Boots size 11

Sorel Women Joan Of Artic III Lace Cozy Waterproof Wedge Chelsea Boots size 11

Sorel

$145.00

1 color, 1 size
  • 11
Zara Women Black Green Leather Elastic Round Slip Chelsea Boots 9US EUR 39

Zara Women Black Green Leather Elastic Round Slip Chelsea Boots 9US EUR 39

Zara

$89.00

1 color, 1 size
  • 9
Lita by Ciara Women Italian Leather Ivory Lace Up Combat Boots size 6US EUR37

Lita by Ciara Women Italian Leather Ivory Lace Up Combat Boots size 6US EUR37

Lita by Ciara

$189.00

1 color, 1 size
  • 6
Jeffrey Campbell Women Daring White Vegan Patent Leather Pointy Toe Boots Sz 11

Jeffrey Campbell Women Daring White Vegan Patent Leather Pointy Toe Boots Sz 11

Jeffrey Campbell

$105.00

1 color, 1 size
  • 11
Load more

Need More Boots?

Check different styles

Women Boot Styles

ANKLE / BOOTIES
COMBAT BOOTS
COWBOY BOOTS
DRESS / OFFICE BOOTS
DESIGNER / LUXE BOOTS
FESTIVAL / PARTY BOOTS
KNEE HIGH BOOTS
HIGH HEEL BOOTS
LUG SOLE BOOTS
LACE-UP BOOTS
MID CALF BOOTS
MOTO / BIKER BOOTS
OVER THE KNEE BOOTS
PLATFORM BOOTS
RAIN / WELLIES BOOTS
WESTERN BOOTS
WINTER / SNOW BOOTS
VINTAGE / RETRO BOOTS

Recently viewed