2000s dress shoes

851 results

Vintage Y2K Marco Delli Dress Shoes Men's 12.5 Tan PonyHair Spots Handmade Italy

$139

Rockport Black Oxford Dress Shoes Men's Size 11 Leather

$70

Calvin Klein Men's Oxfords - Brown - US 11.5 – Y2K Calvin Klein Brown Oxford Dress Shoes …

$51.89

Steve Madden Branner Wingtip Oxford Size 13 Black Leather Dress Shoes

$60

Allen Edmonds Valencia Mens Sz 12 D Black Leather Balmoral Oxford Dress Shoes

$49

Vintage Slick Exotica Red Genuine Alligator Dress Shoes Men's Size 8 Square Toe

$45

Vintage Men's Dress Shoes Loafer Black Size 9.5 Wide Apt. 9 With Box 2000s

$37.99

Florsheim Mens Brown Leather Oxford Dress Shoes Premium Quality

$32

American Vintage Men's Oxfords - Tan/Brown - US 10.5 – Vintage Y2K Tan Leather Oxford Dress Shoes …

$31.41

American Vintage Men's Oxfords - Black - US 12 – Y2K Black Leather Chunky Dress Shoes Size …

$63.70

Croft & Barrow Men's Oxfords - Black - US 11 – Men’s Black faux leather dress shoes - …

$36.76

Uv Signature Wingtip Oxford Dress Shoes Size 11 Black Leather

$65

Men's Oxfords - Red - US 8 – Y2K Leather Dress Shoes Monk Strap Sz …

$63.33

Bostonian Italy Brown Leather Square Toe Dress Shoes Oxfords Mens 12 M 29029

$54.95

Cole Haan Men's Oxfords - Tan/Brown - US 9.5 – Cole Haan Wingtip Oxford Dress Shoes (2 …

$63.69

LLBean size 9.5 handcrafted genuine leather men's black dress shoes/LLBean handcrafted black genuine leather men's shoes

$58

Johnson & Murphy Limited Collection Black Leather Oxford Dress Shoes 10.5 B

$75

Stafford Black Leather Lace Up Dress Shoes Size 10.5

$40

Franco Sarto Buckle Loafer Heels Brown Patent Leather Dress Shoes Women’s 6 M

$39.99

Allen Edmonds Tampa Black Gator Print Loafers Mens 9.5 D Slip On Dress Shoes Leather Luxury Classic USA Great Condition

$50

Tommy Hilfiger Vintage Y2K Brown Leather Derby Dress Shoes Mens Size 9M

$42

Men's Oxfords - Black - US 11 – CASTELLIONE Black Croc Embossed Leather Dress Shoes …

$30.94

Charlotte Olympia Green Suede Leather Platform Pumps Dress Shoes Heels sz 38

$69.99

Y2k Leather Dress Shoes Monk Strap Sz 8 Vintage Oxford Wing Tips Brow Red Tape

$60

Vintage Kenneth Cole Mens Dress Shoes

$54

Rockport Ci8245 Black Leather Oxford Dress Shoes Size 10

$65

Nunn Bush Black Leather Wingtip Oxford Dress Shoes 10 D

$75

Bates Lites Patent Oxford Dress Shoes Size 8W Black

$60

VTG Y2K One212 Womens Brogue Oxfords Size 7.5 Brown Leather Wingtip Dress Shoes

$69.87

MENS BORN LEATHER LACE UP CASUAL DRESS SHOES VINTAGE Y2K BROWN SIZE 10.5

$21.85

Brooks Brothers PEAL & CO Wingtip Loafers Vintage BLACK Dress Shoes Mens 12 $698

$199.99

Vintage Allen Edmonds Delray Split Toe Dress Shoes Brown Size 10 D Made In USA

$79.95

American Vintage Men's Oxfords - Brown - US 8.5 – Vintage Y2K Brown Leather Oxford Dress Shoes …

$45.06

Vintage Y2K Dolce & Gabbana Black Patent Textured Oxford Dress Shoes Men's 10

$94.99

VTG Y2K Leather Classics Men's Brown Leather Slip On Loafers Dress Shoes, Sz 9.5

$31.99

Rockport M4341 Brown Leather Oxford Dress Shoes

$60

Vintage Dockers Mens Size 10 Black Leather Upper Dress Shoes 90-2004 Vtg Y2k

$25.50

Steve Madden Adept Men’s 10.5 Leather Slip On Dress Shoes Brown Y2K VTG Rare

$149.99

Bostonian Italy Brown Leather Square Toe Dress Shoes Oxfords Mens 12 M 29029

$47

Robert Wayne Mens Size US 10 Brown Leather Loafers Square Toe Dress Shoes

$50

Vtg Y2k Levis Oxford Dress Shoes Mens 10.5 Black Leather Plain Toe Classic Derby

$35

Ben Sherman Men’s Size 8 Gent’s Club Leather Dress Shoes Gently Worn

$24.99

Cole Haan Zerogrand Wingtip Oxford Black Leather Dress Shoes Size 11m C26187

$65

Vintage Dockers Men’s Black Leather Square Toe Dress Shoes Lace Up Oxford

$25

Fratelli Mens Oxfords Sz 9.5 M Brown Leather Y2k Square Toe Dress Shoes

$49

BOSS Black Patent Leather Penny Loafers Dress Shoes Size EU 41 / US 8

$110

Cole Haan Men's 10.5 M Burgundy Split Toe Derby Dress Shoes C09440

$64.49

Vintage Y2K Vangelo Black Patent Leather Dress Shoes Tuxedo Oxford Black 3

$25

Bostonian Flexlite Black Leather Oxford Dress Shoes

$65

Ralph Lauren Monkstrap Dress Shoes 10.5 Leather Woven Detail VTG Benchmade Y2K

$98.89
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“2000s dress shoes”

Steve Madden Kabin 12 Y2K Square Toe Black Leather Dragon Sole Dress Shoes

$29

Allen Edmonds Sanford Black Men’s Dress Shoes Wingtip Oxford Size 10 E

$100

Creative Reaction Men’s Black Dress Shoes 11.5 Y2K Gothic Grunge Boho Retro[1D

$31.90

ECCO Black Leather Slip-On Dress Shoes Loafers

$60

Florsheim Mens Oxford Wingtips Dress Shoes Chukka Boots Extra Light Ortholite Comfort Tech Comfortech Brown Tan Genuine Leather Men's 9.5

$24.99

VTG Allen Edmonds Men's Burgundy Leather Tassel Loafers Dress Shoes Size 8.5 D

$68

Clarks Leather Penny Loafers US 8.5 Tan Slip On Dress Shoes

$65

Aldo Black Leather Square Toe Slip On Loafers Dress Shoes Size 45 Us 11.5-12

$33

Venturini Milano Italy Brown Leather Monk Strap Cap Dress Shoes Mens 12 Fancy IT

$63.60

Vintage y2k Rose Gold Metallic Platform Heels . Bamboo Tournament Ankle Strap Open Toe Dress Shoes, Women's Size 8.5

$45

UV Signature Wingtip Oxford Dress Shoes Size 11 Black Leather

$65

Salvatore Ferragamo Black Leather Monk Strap Men's Dress Shoes Size 9 1/2 D Vtg

$300

AGL Womens Sandals Size 38 8 Black Silver Ankle Strap Block Heel Dress Shoes Y2K

$79.84

Bostonian Flexlite Black Leather Oxford Dress Shoes

$65

Stacy Adams Men's Oxfords - Green - US 10.5 – Stacy Adams Men 10.5M Dress Shoes Y2K …

$31.65

Dockers 90-32765 Brown Leather Oxford Dress Shoes Mens 12

$50

Penguin Original Suede Leather Loafers Casual Dress Shoes Gray

$22

Sebago Sebago Penny Loafers Mens 8.5D Black Suede Slip On Dress Shoes Y2K USA Made Handsewn Preppy

$119

Ecco London Slip On Black Women's Size 9 US 40 EUR Heel Pump Dress Shoes 90s Y2K

$19.99

Stacy Adams Genuine Snake Skin Brown Slip On Dress Shoes Men's 8M Leather Exotic

$39.95

Kenneth Cole New York Y2K Men's Dress Shoes 44

$49

Florsheim Dress Shoes Men's 9D Black Leather Classic Lace Up Modern Y2K #23614

$54.97

Fendi Stiletto Heels Platform Open Toe Sandals Grommet Gold Stud Dress Shoes Y2k

$98

Kenneth Cole Ny Captoe And Tennille Y2k Black Dress Shoes

$125

Womens 10 Platform Loafers Slip On Dress Shoes Chunky Y2k Off White 3.5" Heel

$19.65

American Vintage Men's Oxfords - Black - US 10.5 – Y2K Black Leather Oxford Dress Shoes Size …

$55.82

Vintage J Renee Heels Sz 8M Multicolor Made In Hong Kong 90s Leather Dress Shoes

$27.99

Nordstrom Tassel Loafers Size 9 1/2 M Black Leather Dress Shoes

$75

ECCO Men's Loafers - Black - US 12 – Ecco Men's Minneapolis Slip On Dress Shoes …

$51.10

Vintage Womens Italian Designer Cow Hide Leather Hide On Casadei Oxford Dress Shoes size 9.5 Y2K Black Cowhide Leather Casadei Dress Shoes

$395

LA Milano Mens Leather Cognac Dress Shoes Size 11 EEE A121092K

$39

Stacy Adam’s Genuine Leather Alligator-Print Square Toe Dress Shoes Olive 15M

$47.49

Robins men’s black leather slip‑on dress shoes sz 10 moc square toe Y2K

$29.99

G.H. Bass Men's Black Leather Buckle Loafers 7.5 M Vintage Dress Shoes Y2k

$63

Deer Stags Wwt01 Brown Wingtip Dress Shoes

$80

Men's Vintage Johnston And Murphy Classic Black Leather Cap Toe Dress Shoes

$19

Nordstrom Tassel Loafers Size 9 1/2 M Black Leather Dress Shoes

$75

Clarks Men's Oxfords - Black - US 12 – Clarks Mens 12M Dress Shoes Black Leather …

$54.25

Perry Ellis Portfolio Clarkson Oxford Dress Shoes Grey Size 9

$40

Structure Leather Loafers 11 Wide Brown Square Toe Vintage Y2K Dress Shoes

$48

Florsheim Dress Shoes Men's 9d Black Leather Classic Lace Up Modern Y2k #23614

$55

Vintage Bachrach Mens Black Leather Double Monk Strap Wingtip Dress Shoes 11

$38

Nwot Aldo Women Y2k Leather High Heels Formal Dress Shoes Size 8

$26

Dockers Dockers Black Leather Derby Dress Shoes 12W Wide Square Toe

$38

Gold Womens High Heel Rhinestone Strap Dress Shoes W/ Gold Clutch Bag Fairy Y2K

$35.99

Bostonian Vero Cuoio VTG Men's Leather Loafers Dress Shoes Sz 10M Burgundy Italy

$75

Allen Edmonds Strand Cap-Toe Oxford Dress Shoes Size 8.5

$114

Rockport Men's Oxfords - Brown/Orange - US 12 – Rockport Channer brown leather dress shoes Mens …

$26.95

Steve Madden Natali 5" High Heel Platform Gold Glitter Dress Shoes Womens Size 7

$18.42

ECCO Men's Oxfords - Black/Brown - US 10 – Y2K Ecco Black Leather Oxford Dress Shoes …

$48.48