2000s dresses

1,195 results

Preloved Men's Shorts - Tan/Cream – 6Crayon Long Bermuda Pleated Dress Shorts 32 …

$84.70

LRL Ralph Lauren Wool Overcoat Mens XL 46 Charcoal Gray Dress Vintage Y2K 90s

$99.99

Stacy Adams Mens Shoes 11M Leather Slip On Dress Square Toe Loafers White Retro

$31.54

VTG St Croix Made in Italy Mens L Shirt Blue Plaid Button Casual Dress Luxury

$29.95

Tommy Hilfiger Men's Shirt - Yellow/Cream – Tommy Hilfiger Ithaca Light Yellow Striped Dress …

$24.85

Calvin Klein Men's Shirt - Blue – Distressed Calvin Klein denim long sleeve dress …

$27.48

Vintage Men's Shirt - Blue/Multi – 00s J Crew Multi-Colored Striped Dress Polo …

$47.95

Bobby Jones Golf Polo Men's Large Shirt Tan & Black Casual Dress Athleisure

$19.99

Jordan Men's Sneakers - White/Blue – #sneakers #jordan #streetwear #dressed #y2k Jordan Air …

$79.45

Farrell dress pant men 32R Navy wool event formal holiday giftable new retro Y2K

$20.70

Geoffrey Beene Men's Shirt - Navy/Blue – Geoffrey Beene navy blue striped button-up dress …

$26.95

Nordstrom Men's Shirt - Blue/Multi – Vintage Lucerne for Nordstrom 100% Cotton Dress …

$26.95

Men's Casual Dress Tallia Turquoise Medallion Shirt XL

$90

Vintage 90s Y2K Polo Ralph Lauren Blue Green Men's Golf Dress Plaid Shorts SZ 42

$25

Preloved Men's Oxfords - Black – Caporicci Black Leather Square Toe Derby Dress …

$63.69

Men's Loafers - Black – Size 12 David Stone Black Dress Square …

$31.15

Men's Shirt - Red – Affliction grunge style Zoyla red striped dress/ …

$37.45

Bragano Cole Haan Dress Loafer Mens 13 Brown Leather Suede Tassel Cap Vintage

$78

Vintage Tommy Hilfiger Button Up Shirt Men's Size XL Long Sleeve Dress Plaid

$29

Y2k Vesuvio Napoli Italian Red Paisley Print Dress Vest

$30

Vintage Stacy Adams Black Wool Felt Fedora Hat, Classic Men's Dress Hat, Satin Lined, Early 2000s, Feather Hat, Gangster Fedora

$54

Charles Tyrwhitt Classic Purple Mens Dress Button Down Professional Shirt

$36

Vtg ONISS PARIS Swiss Watch Men Cushion Y2K Date Cushion Case Dress NEW BATTERY

$71.20

ALDO Men's Black Leather Slip-On Dress Loafers Cross Accent Square Toe

$25.67

Dr. Martens Shoes 2b89 Mens Size 12 Brown Leather Oxford Casual Dress Y2k 90s

$39

Jd Fisk Navy Blue Saddle Tan Genuine Leather Suede Dress Oxford Shoes Sz 11

$27

Ed Hardy dress

$33.18

Men's Shirt - Multi – Y2K Skater Tony Hawk Plaid Embroidered Dress …

$21.69

JOHNSON & MURPHY COLLARD DRESS CASUAL PARTY POLO SHIRT MEN XL ORANGE BLUE TAGLES

$24.99

Nike Vintage Y2K Dress Nylon Shorts Stretch Men's XL Blue 4 pocket

$26

Orvis Men's Shirt - Multi/Multi – Orvis Mens' Button Down Casual Dress Plaid …

$26.90

Vintage Polo Ralph Lauren Shorts Adult 38 Green Dress Golf Y2K 90s Formal Preppy

$39.99

Charles Tyrwhitt Mens Slim Fit Long Sleeve Check Preppy Dress Suit Shirt

$33

Vintage Us Military Battle Dress Uniform Field Jacket M81 Woodland Camo Large

$56

Hollister Shirt Mens Medium Dress Blue Plaid Long Sleeves Button Up Y2K Vintag

$24.99

Antonio Zengara Men's Brown Suede Slip-On Dress Loafers Metal Bit US 7.5

$45

Vintage Hugo Boss Plum Striped And White Dress Shirts Set Of 2 Men’s Xl Euc

$48

Laredo Men's Black Leather Dress Cowboy Boots Size 13D Style 68610

$55

Men’s Christian Dior Dress Polo Shirt Button Up Preppy Designer Casual Summer

$45

Jil Sander Shoes Mens Leather 9 Derby Dress Luxury Lace Up Gray Beige Tan

$83.57

Skechers Men's Oxfords - Black – Skechers Tom Cat Oxford Utility Dress/Work Shoes …

$47.95

PULSAR (by Seiko) MEN'S VD74-X001 NOT-WORKING 50M DRESS CHRONO WATCH CASE PW9011

$30

USA made TORINO elite RINGMARK LIZARD dress brown Belt 40

$68

Vintage English Laundry Fedora New Old Stock Trilby Stingy Brim Dress Hat Medium

$55

Number (N)ine Number (N)ine - AW04 Corduroy Dress Pant

$200

Dr. Martens Shoes 2b89 Mens Size 9 Brown Leather Oxford Casual Dress Y2k 90s

$40

Utility Men's Vest - Tan – VTG 90s Y2K Dress Town York Men …

$35.34

90's / Y2K Ralph Lauren Polo Knit Dress Shorts

$30

Apt. 9 Y2K Kingman Men's Black Leather Loafers Slip On Dress Career Shoes size 13

$45

Cole Haan Shoes Mens 10.5 Black Leather Air Vtg Kiltie Loafers Dress Y2k 90s

$50
Save Search
“2000s dresses”

Y2K Cher Dressed to Kill Tour 2014 Concert Tee

$45

Polo Ralph Lauren Charcoal Chalk Stripe Dress Rugby Shirt Long Sleeve Polo XL

$399

Hickey Freeman Checkered Mens Dress Button Down Long Sleeve Shirt

$23

Fortino Landi Vest Mens 3XL Black Formal Dress Waistcoat Prom Wedding Waistcoat

$22.49

Dress Suit Tie Mens Red Beige Tartan Plaid Wide Scottish Y2K STUART KENT Japan

$25.84

Thomas Pink Button Down Pink Plaid Long Sleeve Dress Suit Shirt Mens

$23

RARE DKNY Black leather Chunky Dress Oxfords 90s Y2K Made In Spain

$125

Lauren Ralph Lauren Plaid Dress Suit Mens Shirt 15.5 (32 - 33)

$59

Stacy Adams Men's Oxfords - Grey/Black – Stacy Adams Grey Silver Crocodile Oxford Dress …

$20.93

Goonies Movie Skulls Black Shirt Men's XL Casual Dress Button Up Short Sleeve

$29.99

Charles Tyrwhitt Mens Slim Fit Long Sleeve Check Preppy Dress Suit Shirt

$40

Polo Ralph Lauren Men's Shorts - Blue/White – Polo Ralph Lauren dress shorts Measurements in …

$14.86

American Vintage Men's Oxfords - Brown/Tan – Moc toe brown leather lace up dress …

$25.90

VTG Wrangler Wrancher Plaid L/S Pearl Snap Shirt Sz Medium Western Dress Y2K 90s

$19.95

Balenciaga Men’s Dress Tassel Loafers

$150

Skeleton Chief Y2k Aop Indian Native American Head Dress Mens M Skull Tshirt Vtg

$30

Vintage Ascot Chang Men’s Button-Up Shirt Long Sleeve Houndstooth Casual Dress Blue Plaids & Checks Regular Size L

$30

Mecca Shirt Mens L Button Up Dress Vintage Streetwear 90s Y2K Rap Burgundy

$17.99

Polo Ralph Lauren Andrew Shirt Mens 18 34/35 Grey Stripe Oxford Dress Retro Y2k

$22

Peter Millar Shirt Xxl Men's Blue Purple Striped Y2k Vintage Button Up Dress Tee

$21

Vintage Y2k 90's French Kuff Blue Denim Jean Overall Dress Size 2X Adjustable

$24.99

Vintage Ralph Lauren Pastel Pony Button Blue Green Pink Shirt 17.5 Dress Y2k Vtg

$25

Tommy Hilfiger Shirt Mens 16 Blue White Striped Button Up French Cuff Dress Y2K

$21.99

Vtg LL Bean Corduroy Shirt Mens Medium Red Button Up Traditional Fit Dress Y2K

$21.59

Cyma Le Locle Swiss Made Men's Black Dial Dress 37mm Watch Two Tone Quartz

$250

Vintage VINTAGE Hollister Shirt Mens Medium Blue Plaid Long Sleeves Button Up Y2K Dress

$40

O'Neill Men's Shorts - Brown/Grey – O'Neill size 30 grey dress shorts with …

$16.45

John Blair Red Two Pocket Shirt Men's Medium Pullover Long Sleeve Casual Dress

$18.87

Men's Vintage Y2K Preppy Express Producer Pinstripe Dress Slacks Size 30x30

$29.99

Vtg Balthazar Paris Leather Lace Up Oxford Shoes Mens EU 40 Tan Casual Dress Y2K

$25.62

Vintage USMC Eighty Eight Military Dress Alpha Shirt Sz L

$22.97

Bass Flex 2 Mens 10 M Brown Leather Gel Oxfords Bike Toe Dress Casual Shoes

$25.50

Dior Men's Shirt - Black/Navy – Dior Homme - AW02 "Reflexion" Cotton Dress …

$336.70

Banana Republic Polo Shirt Linen Blend Black Men’s XL Dress Short Sleeve VTG Y2K

$21.95

Polo Ralph Lauren VINTAGE Polo Ralph Lauren Button Up Shirt Mens XL Plaid Pony Long Sleeve Dress Blue

$32

Apt. 9 Men's Oxfords - Black – Black leather square toe lace up dress …

$32.19

Vintage Men's Shirt - Grey – Vintage 2000s casual dress wear style button …

$16.45

Ralph Lauren Shirt Men Xl Tan Brown Button Up Twill Denim Blake Dress Vtg Y2k *

$25

Uniqlo Men's M Gingham Check Long Sleeve Button Down Shirt Casual Dress Y2k

$20

Savane Dress Pant Men 38x30 Silkworks Casuals Tencel Pleated Cuffed Academia Y2K

$16.77

Savane Dress Pant Men 38x30 Silkworks Casuals Tencel Pleated Cuffed Academia Y2k

$21

Ralph Lauren Ralph Lauren Shirt Mens 17 Blue Dress Button-Down Long Sleeve Cotton Regular Classic Casual Business 2000s Mens

$30

Mens Brooks Brothers Spread Collar Plaid Dress Work Dress Formal Shirt

$32

Timberland Men's Shirt - Blue – Vintage timberland striped emo button up dress …

$16.45

Polo Ralph Lauren Curham Shirt Button Up Dress Classic Fit Blue Stripe 16 1/2 L

$52.94

Polo Ralph Lauren Men's Shirt - White/Black – Y2K Polo Ralph Lauren Button Up Dress …

$26.94

VTG Jos. A. Bank Tie Navy Silk Medallion Geometric Italy Handmade Work Dress Y2K

$24.44

Stafford Tie Men’s Black & Brown Geometric Pattern Silk Business Office Dress

$18

Badgley Mischka Fw 2000 Floral Burnout Velvet Dress With Embellishments

$1,070

Polo Ralph Lauren Men's Shirt - Yellow/Orange – Polo Ralph Lauren Orange Pony Button Dress …

$11.19