2000s dress shoes

778 results

Rare 1990s Vintage Vans Mel Mens Dress Shoes Suede Leather Size 10.5 Korea 9510

$24.76

Stacy Adams Men's Size 13 Blue Leather Crocodile Print Oxford Dress Shoes Y2K

$35.40

Clarks Men's Oxfords - Black – Clark’s Black leather dress shoes Mens Size …

$28.82

Rockport Men's Oxfords - Black – Vintage Y2K Rockport Black Leather Dress Shoes …

$45.06

American Vintage Men's Boat shoes - Brown/Burgundy – Vintage Y2K Brown Boat Leather Dress Shoes …

$32.20

Vintage Y2K Cole Haan Gray Suede Wingtip Brogue Oxford Dress Shoes

$47

Steve Madden Black Square Toe Derby Dress Shoes Men’s 11.5

$30

Allen Edmonds Fairfax Wholecut Oxford Dress Shoes Men’s 11 D Walnut Brown 1125

$80.10

American Eagle Y2K Red Suede Flats Size 7.5 Womens Dress Shoes Casual Bow Tie

$21.91

VTG Cole Haan Bragano Dress Shoes Mens 8.5 D Brown Leather Cap-Toe Made In Italy

$29.99

Allen Edmonds Delray Split Toe Chili Brown Leather Dress Shoes Mens Size 13 D

$99

Nunn Bush Black Tassel Loafers Leather Vintage Dress Shoes 10.5M

$35

Cole Haan Vintage Y2K Gray Suede Wingtip Brogue Oxford Dress Shoes

$47

Parker & Sky Tan Leather Cap Toe Oxford Dress Shoes Men's 11

$65

Vtg Florsheim Men's Black Leather Loafers Slip On Moc Toe Dress Shoes 10 E Wide

$44

Prada Derbys Brown Men 8.5 Leather Strap Platform Dress Shoes Designer Y2K

$242

Vintage U.S. Brass Brown Leather Oxford Dress Shoes 5900/2

$60

Rockport Men's Oxfords - Brown – Rockport brown leather Oxford dress shoes. Definitely …

$32.20

Chunky Heel Ankle Boots Lace Up Side Zip Retro Y2k Platform Dress Shoes

$132

Elegant Italian Men's Dress Shoes Genuine Leather 41 Us 8 Y2k

$59

Gravati Oxford Mens 8W Brown Leather Split Toe Lug Sole Italian Dress Shoes

$64

Deer Stags Black Leather Oxford Dress Shoes – Men’s 8.5 Wide Comfort Work

$29.99

Vintage Tan Leather Cap Toe Dress Shoes

$35

Vintage Y2K Sutor Mantellassi Norvegese Split Toe Derby Dress Shoes 10.5 44.5

$129.95

Cole Haan Brown Genuine Leather Oxford Dress Shoes Business Office Career Sz 9 D

$30

Boemos Men’s 14 Black Leather Vintage Style Dress Shoes Square Toe Derby Italy

$115

Vintage Florsheim Custom Playboy Bunny Dress Shoes Mens Leather Spectators

$248

Nina Womens Silver Grey Open Toe Evening Formal Heel Dress Shoes Sz 8.5 Y2K VTG

$34.99

Franco Sarto Buckle Loafer Heels Black Patent Leather Dress Shoes Women’s 7

$35

Paolo De Marco Size 17 Wide Genuine Alligator Men's Oxford Derby Dress Shoes

$122

BLACK BROWN Mens 13 Leather Penny Loafers Slip On Dress Shoes Classic TPE04

$99.99

Trotters Brown Woven Leather Dress Shoes | Size 5 (New Old Stock)

$69.99

Clarks Women's Leather Boots - Tan/Brown – Tan Brown Leather Ankle Dress Shoes Booties …

$19.60

Men's Pink Tux Lace Up Satin Striped Patent Sz 13 Square Toe Dress Shoes Viotti

$63.25

Stacy Adams Men 12m Dress Shoes Y2k Square Toe Gray Exotic Embossed Leather

$29

HTF Genuine Men BALLY Prestige Aris Black Leather Oxfords Dress Shoes Size 9 EEE

$295

BASS Astrid Womens Pumps Heels Leather Dress Shoes Comfort Black Size 8.5

$23.45

Steve Madden Men's Oxfords - Black/White – Steve Madden Oxford Dress Shoes Maxxim Mens …

$16.44

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

$50

Dockers Brown Leather Oxford Dress Shoes

$45

Cole Haan Pinch Tassel Loafers Men's 11B Brown Leather Dress Shoes 03507

$34.99

Women's T-Strap Mary Jane Platform Pumps Chunky Heel Dress Shoes

$83

Grenson Mens 11 Boots Black Dress Shoes Leather Cap Toe Lace Up Classic 5085 01

$104

Stacy Adams Mens 13w Oxford Dress Shoes Black Leather Square Toe Formal Classic

$34

Sebago 71-733 Men's Size 9C Brown Leather Apron Toe Derby Dress Shoes USA

$23.10

Vintage Cole Haan Brown Pebbled Leather Penny Loafers Dress Shoes Y2k Mens 8 W

$57

Y2K Brown Leather Derby Oxfords Lace Up Dress Shoes Men’s Sz 8.5 m

$29.99

Allen Edmonds Byron Black Leather Cap Toe Oxfords Dress Shoes 12C w/ Shoe Trees

$65

Vintage Prada Italy Designer Dress Shoes Mens 7.5US Square Toe

$150

Rothy's Cloud Grey Birdseye The Point Flats Size 6 Dress Shoes Preppy Y2k Womens

$45
Save Search
“2000s dress shoes”

Vintage Cole Haan Blucher Oxford Dress Shoes Size 8d Y2k

$22

AM Exclusive Shoes Men's Black Gray Spiked Studded Loafers Dress Shoes Size 12

$39

Clarks Penny Loafers Mens UK 9.5 Black Leather Slip Ons Dress Shoes Vintage

$47.99

Vintage Bass Derby Round Toe Dress Shoes Mens 9 M Brown Leather Y2k

$30

Goodfellow & Co. Men's Oxfords - Brown – Men's Brown Cap Toe Oxford Dress Shoes …

$21.65

Stacy Adam Vintage Brown Leather Dress Shoes Size 9M

$40

Vtg. STONE Black Leather Square Toe Lace Up Dress Shoes EU41 US 8 Made in France

$22.49

Baker-Benjes Dress Shoes, Men 9bb pics For Number , Black Genuine Leather, Italy

$44.11

Air Jordan Leather Boot Black Mens Sz 10 With Damage Dress Shoes

$35

Nine West Women's 8 Brown Leather Monk Strap Ankle Boots Pointed Toe Dress Shoes

$15

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

$63.69

Vintage ALFANI Mens 9.5 Leather Square Toe Loafers Oxford Dress Shoes Slip On

$124.99

Caporicci Black Leather Square Toe Derby Dress Shoes Made In Italy Mens 8.5

$60

Kate Spade Heeled Slides Dress Shoes For Women, Size 6.5

$38

Stacy Adams Men 12M Dress Shoes Y2K Square Toe Gray Exotic Embossed Leather

$21.38

Vintage Prada Black Leather Perforated Derby Dress Shoes Sz 11

$450

Vintage Men'sG.H Bass & Co Weejuns Sz 9.5M Burgundy Marietta II Dress Shoes.

$65

Vintage Tan Leather Cap Toe Dress Shoes

$35

Reaction Kenneth Cole Dress Shoes Men's 10 Brown Leather Monk Strap Y2K Office

$31.10

Vintage Johnston & Murphy Men's Dark Brown Leather Loafer Dress Shoes~9.5m

$44

Vtg Men's Johnston & Murphy Black Biltrite Polished Leather Oxford Dress Shoes

$55

AK Anne Klein I Flex Beige/Black Ballet Flats Size 7.5 Boho Y2k Dress Shoes Slip

$28

Florsheim Royal Imperial lace up oxford dress shoes

$65

Vintage Y2k Structure Black Leather Square Toe Oxford Men Dress Shoes Lace Up 10

$29

Florsheim Mens 12D Oxford Dress Shoes Black Leather Square Toe Classic Formal

$39

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

$69.99

Nunn Bush Men's Oxfords - Brown – Nunn Bush Leather Oxford Dress Shoes Mens …

$53.08

Johnston & Murphy Vintage Y2k Leather Wingtip Dress Shoes

$60

Men Allen Edmonds Dellwood Dress Shoes Black Suede Oxford Split Toe Size 9.5D

$125

Ecco Mens 7.5 Oxford Brown Suede Lace Up Leather Square Comfort Dress Shoes 40EU

$46.55

Nunn Bush Black Leather Oxford Dress Shoes Size 9 D

$70

Vintage 2000s Apt 9 Men's Dress Shoes With Original Box Black Size 11 Wide

$26.59

Johnston & Murphy Vintage Y2K Leather Wingtip Dress Shoes

$60

Vintage Arizona Dress Shoes Womens 9.5 M Black Chunky Y2k Block Heel

$18

Via Spiga Womens Pumps Size 8.5 Black Patent Platform Block Heel Dress Shoes Y2K

$59.87

Kenneth Cole Monk Strap Dress Shoes Men 11.5 Brown Leather Loafer Y2k Italy Made

$45

Mens Guess Gray Suede,Slip On Dress Shoes. Like New Size 9

$28

Vintage David Eden Lizard Skin Alligator Patchwork Oxford Dress Shoes Mens 9.5

$119.99

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

$25.50

Rare NIB Vintage 2001 Candies Trax-Grizzley Brown Women’s Size 6.5 Dress Shoes!

$59.99

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

$38

Nunn Bush 81074-221 Brown Leather Oxford Dress Shoes

$65

CASTELLIONE Black Croc Embossed Leather Dress Shoes Men's Size 11 Formal

$39.99

Vintage 2000s Giorgio Armani Men’s Dress Shoes EU43 US10 – With Box & Dust Bags

$89.99

David Eden Exotic Crocodile Teju Lizard Emerald Green Mens Derby Dress Shoes 11M

$99.99

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

$22

Womens Mary Jane Platform Pumps Chunky Heel Ankle Strap Round Toe Dress Shoes

$84

Men's Black Cap Toe Dress Shoes Oxford Lace Up Size 13 Majestic Collection

$17.60

Florsheim Comfortech 8291-01 Black Leather Oxford Dress Shoes

$60

Dexter Black Leather Oxford Cap Toe Dress Shoes Sz 8.5M Classic

$17.99