2000s dress shoes

661 results

Bass Revere Men's Brown Oxford Dress Shoes Size 9

$65

Johnston & Murphy Vintage Burgundy Leather Oxford Dress Shoes

$65

Dr. Scholl's Men's Black Leather Casual Dress Shoes

$40

Sonoma Life & Style Black Cap Toe Dress Shoes

$40

Clarks Unstructured Black Leather Cap Toe Oxford Dress Shoes

$50

Nunn Bush Men's Oxfords - Black – Nunn Bush leather semi casual dress shoes …

$16.45

Clarks Unstructured Black Leather Cap Toe Oxford Dress Shoes

$50

Vintage Costume National Homme Men's Black Leather Square Toe Dress Shoes 11

$225

Rockport Leather Oxfords: Cognac Brown Lace-Up Dress Shoes, Size 11

$54.99

BKE Zach Chelsea Boots Black/Brown Round Toe Men’s Size 9 Dress Shoes Preppy Y2K

$29.99

Vintage Y2K Cole Haan Gray Suede Wingtip Brogue Oxford Dress Shoes

$47

90s early 2000s SANTONI Italy Men's 10 Black Leather Penny Loafers - Italian Luxury Dress Shoes - Classic Orange Sole Edition

$220

Men's Loafers - Brown – Steve Harvey Sinclair men's dress shoes in …

$125.65

Vintage Y2k Drew Black Leather Penny Loafers Business Casual Dress Shoes 10.5

$35

Vintage Y2K Bass Leather Dress Shoes Mens 10M Brown Lace Up Chunky Academia

$27.97

Nunn Bush 81074-221 Brown Leather Oxford Dress Shoes

$65

Stephan Bossi Men's Black Slip-On Dress Shoes 10.5m Casual Office Y2k Grandpa

$45

J.Renee Womens Velvet Dress Shoes Y2K sz 8.5W

$71.10

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

$25.90

Rockport A13013 Black Leather Lace Up Dress Shoes

$40

Liz Baker Classic Black Leather Block Chunky Heels Slip On dress shoes size 9

$35

Dr. Martens Chunky Oxford Leather Dress Shoes 11306 Mens Sz 11 Y2K Era Doc Brown

$47.95

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

$55

Gucci Gucci - Patent Leather Black Tuxedo Dress Shoes

$202

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

$395

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

$27

Kenneth Cole Monk Strap Dress Shoes Men 11.5 Brown Leather Loafer Y2K Italy Made

$40.49

Johnston & Murphy Vintage Y2K Leather Wingtip Dress Shoes

$60

Kenneth Cole New York Y2K Men's Dress Shoes 44

$49

Vintage DEXTER Mens 10 Faux Leather Round Toe Oxford Dress Shoes BROWN

$39.99

Alfani Paul Wingtip Oxford Dress Shoes Brown Leather Size 9.5

$45

Men's Y2K Steve Madden Stoked Brown Dress shoes size 13

$35

Allen Edmonds Mapleton Brown Leather Bicycle Toe Derby Dress Shoes Mens Sz 9.5 D

$46.76

Steve Madden Men’s Velvet Loafers/ Dress Shoes

$38

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

$22.49

Florsheim Royal Imperial lace up oxford dress shoes

$65

Bostonian Classics First Flex Black Oxford Lace Up Mens Leather Dress Shoes 9.5m

$45

ALLEN EDMONDS Black Leather Dress Shoes Men's 11 Hillcrest Oxford Derby USA

$195

Red Wings Dunoon Oxford Brown Leather Brogue Dress Shoes 41570 Mens 9 D USA

$74.99

Vintage Florsheim Custom Playboy Bunny Dress Shoes Mens Leather Spectators

$161.20

A. Testoni Black Leather Apron Toe Oxford Dress Shoes Sz 10M Italy

$98

Faux Leather Platform Chunky Heel Loafers Slip On Lug Sole Dress Shoes

$85

Vibram Diego's Vintage Alligator Skin Men's Dress Shoes 1990's Early 2000's

$193.25

Zelli Derby Style Ostrich Men's Brown Dress Shoes Size 9.5

$299

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

$74.95

Allen Edmonds Men's Oxfords - Brown – Allen Edmonds Men 12D Dress Shoes Brown …

$54.25

Stephan bossi Men's Black Slip-On Dress Shoes 10.5M casual office Y2K grandpa

$45

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

$42

Armani Exchange Women's Loafers - White/Cream – Rare Armani Exchange white dress shoes Y2K …

$30.10

Romi de Luca Cognac Leather Square Toe Dress Shoes Mens 9 Y2K

$40
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“2000s dress shoes”

Moschino Dress Shoes Baby Doll Heels Logo Pumps Velvet Y2k Vintage

$68

ECCO Mens 8-8.5 Oxford Brown ST.1 Hybrid Textured Leather Business Dress Shoes

$49

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

$35

Sam & Libby Black Strappy Dress Shoes: Open Toe Block Heel, Size 7.5M

$32.50

Maison Margiela Maison Margiela Canvas Dress Shoes

$181

Pointed Toe Kitten Heel Slingback Pumps Breathable Knit Work Dress Shoes Y2k

$85

Sandro Moscoloni Men 12D Brown Leather Oxford Square Toe Lace Up Dress Shoes

$42.91

Hillard and Hanson Dress Shoes Women’s Size 5.5 Straps 2” Heels Vintage Y2K

$25.46

Platform Strappy Heels Open Toe Ankle Strap Square Party Sandals Y2k Dress Shoes

$68

Perry Ellis Portfolio Clarkson Oxford Dress Shoes Grey Size 9

$40

Vintage Y2k Cole Haan Gray Suede Wingtip Brogue Oxford Dress Shoes

$27

Vintage Giorgio Brutini Blocked Black Men's Leather Dress Shoes Y2k Ready!

$35

Pop Women Black Trust Block Heel Platform Y2k Mary Jane Dress Shoes Size 7.5

$34

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

$42

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

$25.50

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

$34

Stacy Adams Men 10.5m Dress Shoes Y2k Square Toe Olive Green Exotic Leather

$33

Y2K Kenneth Cole Chunky Oxford Dress Shoes Mens 7.5 Brown Leather Italy Preppy

$43.87

Aerosoles Women's Soft Suede Lace Dress Shoes Loafers Beige 2" Stack Heel- -8.5

$25.99

Bachrach Oxford Dress Shoes Mens Sz 12 Brown Leather Split Square Toe Corporate

$28.87

Stacy Adam Vintage Brown Leather Dress Shoes Size 9M

$40

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

$19.60

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

$55

Vintage Tan Leather Cap Toe Dress Shoes

$35

Bruno Magli Burgundy Leather Dress Shoes Oxford Cap Toe Italy Size 10 EU 42.5D

$39.99

Cole Haan Air Mens Tassel Loafers 9.5 M Black Leather Casual Dress Shoes Classic

$45

Salvatore Ferragamo Italy Beige Yellow Leather Dress Shoes Womens 8.5 AAAA Heels

$125

Mezlan Brown Suede Oxford Dress Shoes - Mens 12

$101

Vintage Y2K Skechers Italy Monk Strap Leather Dress Shoes Mens Sz 12 Brown RARE

$53.99

Allen Edmonds Fairfax Dress Shoes Mens size 8 Brown Leather Wholecut Oxfords USA

$83.20

CROFT & BORROW Mens 10W 10 W Ortholite Oxford Dress Shoes Square Toe Comfort

$49.99

Steve Madden Flemming Men’s 13 Brown Leather Square Toe Y2K Loafers Dress Shoes

$20.29

Stacy Adams Woven Tassel Loafers Men's 9.5M Brown Leather Y2K Classic Preppy Old Money Dress Shoes

$39.99

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

$21.65

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

$29

POP Women Black Sinclaire Block Heel Platform Y2K Mary Jane Dress Shoes Sz 8.5 M

$30

Nina Women's Pumps - Silver – Nina Y2K style dress shoes, sparkly Enrica …

$30.10

Brushed Calf Leather Oxford Dress Shoes - Men's Size 12

$21.99

Mens Giorgio Brutini Oxford Two-Toned Dress Shoes Size 10 1/2

$35

RARE COACH Womens Designer Pumps: Designer Shoes, Coach Leather Pumps, 6B, Black Leather Shoes, Coach, Made in Italy, Rare Dress Shoes,Euc

$175.99

Mens 8 Dr Martens Willis Stud Creeper Punk Black Dress Shoes Womens 9 Grunge Y2K

$134.95

Nunn Bush Leather Oxford Dress Shoes Mens SZ 9.5C Plain Toe Y2K Retro Old Money

$49.89

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

$35

La Milano Men’s 11 Black Leather Dress Shoes Gothic Street Retro Y2K Cottage[3D

$23.90

Johnston & Murphy Men's Loafers - Brown – Really cool Johnston and Murphy dress shoes …

$19.60

Vintage St. Michael Black Leather Semi-Brogue Oxford Shoes | Authentic Marks & Spencer Men's Formal Dress Shoes UK 9 | US 10 | EU 43

$220

Johnston & Murphy Men’s Tassel Loafers Size 11M Brown Leather Kiltie Classic Dress Shoes

$55

Bcbgirls Peep Toe Ankle Strap Heels Women’s Brown Gold Scallop Dress Shoes

$31

Zengara Brown Leather Square Toe Oxford Brogue Dress Shoes 9.5 M Lace Up Preppy

$20

Touch Ups Women's Dress Shoes Size 8 M Black Open Toe kitten heels rhinestones

$20