Shop Crossdrossing Vintage Dresses

Sponsored
About our ads
$485.00
Stacees Vintage Bridal Wedding Dress Plunging V-Neck Ball Gown With Chapel Train
Stacees.com
$485.00
Stacees Vintage Bridal Wedding Dress Plunging V-Neck Ball Gown With Chapel Train
Stacees.com
$54.99
Floral Vintage Boho Maxi Dress
WAVLYNN
$54.99
Floral Vintage Boho Maxi Dress
WAVLYNN
$38.50
Cross-Over Midi Dress
WAVLYNN
$38.50
Cross-Over Midi Dress
WAVLYNN
$39.99
3/4 Sleeve 1950S Elegant Lace Floral Embroidery Swing Dress M Apricot
modernonlinemart.com
$39.99
3/4 Sleeve 1950S Elegant Lace Floral Embroidery Swing Dress M Apricot
modernonlinemart.com
$32.38
$49.19
Vintage Elegant Women's 1920S Party Dress With Sequin Embroidery, Form-Fitting Patchwork Tassel Boat Neck Bodycon Cocktail Dress Flapper Dress Great Gatsby Dress 20'S Vintage Thanksgiving Women Outfit Black Homecoming Dress C
shein
34% off
$32.38
$49.19
Vintage Elegant Women's 1920S Party Dress With Sequin Embroidery, Form-Fitting Patchwork Tassel Boat Neck Bodycon Cocktail Dress Flapper Dress Great Gatsby Dress 20'S Vintage Thanksgiving Women Outfit Black Homecoming Dress C
shein
$36.99
$69.99
Women Retro Dresses Vintage 1950S Short Sleeve Prom Rockabilly Swing Dress - L, Yellow
tohittheroad.com
47% off
$36.99
$69.99
Women Retro Dresses Vintage 1950S Short Sleeve Prom Rockabilly Swing Dress - L, Yellow
tohittheroad.com
$150.00
Stunning Rare Ramona Rull Vintage 1960'S 1970'S Bohemian Embroidered Kaftan Dress
Etsy
439
$150.00
Stunning Rare Ramona Rull Vintage 1960'S 1970'S Bohemian Embroidered Kaftan Dress
Etsy
$17.33
$26.89
Red Off-Shoulder Mesh 2In1 Trumpet Sleeve Long Sleeve Women's Dress,Western,Vintage,70S,The Bachelorette,Christmas,Red Dress,Christmas Dress,New Year Dress,M
shein
35% off
$17.33
$26.89
Red Off-Shoulder Mesh 2In1 Trumpet Sleeve Long Sleeve Women's Dress,Western,Vintage,70S,The Bachelorette,Christmas,Red Dress,Christmas Dress,New Year Dress,M
shein
$35.99
Belle Poque Women's Vintage Square Neck Dress 2026 Summer Short Sleeve Layered Tiered Ruffle A-Line Swing Midi Dress
Amazon.com
603
Free shipping
$35.99
Belle Poque Women's Vintage Square Neck Dress 2026 Summer Short Sleeve Layered Tiered Ruffle A-Line Swing Midi Dress
Amazon.com
$115.00
Vintage Floral Dress Puffy Sleeves Cottage Core Dress Prairie Dress 1920S Victorian Edwardian Dress Floral Pattern Pastel Floral Print Roses
Etsy
444
Free shipping
$115.00
Vintage Floral Dress Puffy Sleeves Cottage Core Dress Prairie Dress 1920S Victorian Edwardian Dress Floral Pattern Pastel Floral Print Roses
Etsy
$135.00
Vintage Late 60S Psychedelic Tori Richards For I Magnin Hawaiian Maxi Dress
Etsy
930
$135.00
Vintage Late 60S Psychedelic Tori Richards For I Magnin Hawaiian Maxi Dress
Etsy
$185.00
Unique Vintage 1950S Sweetheart Swing Dress In White Cat Print At Nordstrom, Size Medium
Nordstrom
$185.00
Unique Vintage 1950S Sweetheart Swing Dress In White Cat Print At Nordstrom, Size Medium
Nordstrom
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Large, Green
Kohl's
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Large, Green
Kohl's
$75.99
Women's Vintage 50S Dress Cocktail Sleeveless Square Neck Midi Floral A-Line Dresses, Size: Large, Beige
Kohl's
Free shipping
$75.99
Women's Vintage 50S Dress Cocktail Sleeveless Square Neck Midi Floral A-Line Dresses, Size: Large, Beige
Kohl's
$230.00
Colonial 18th Century Dress Cotton Historical Day Gown Floral
Etsy
1K+
Free shipping
$230.00
Colonial 18th Century Dress Cotton Historical Day Gown Floral
Etsy
$153.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Blue Sky, Floral At Nordstrom, Size Small
Nordstrom
$153.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Blue Sky, Floral At Nordstrom, Size Small
Nordstrom
$160.00
Unique Vintage 1940S Sweetheart Button Front Swing Dress In White Lady & Tramp Print At Nordstrom, Size Medium
Nordstrom
$160.00
Unique Vintage 1940S Sweetheart Button Front Swing Dress In White Lady & Tramp Print At Nordstrom, Size Medium
Nordstrom
$120.98
Womens Vintage V Neck Ruffle Split Bridesmaid Party Long Dress, Women's, Size: Medium, Red
Kohl's
Free shipping
$120.98
Womens Vintage V Neck Ruffle Split Bridesmaid Party Long Dress, Women's, Size: Medium, Red
Kohl's
$138.00
Unique Vintage 1950S Sweetheart Neckline Swing Dress In Light Pink Roses Print At Nordstrom, Size Medium
Nordstrom
$138.00
Unique Vintage 1950S Sweetheart Neckline Swing Dress In Light Pink Roses Print At Nordstrom, Size Medium
Nordstrom
$123.00
Unique Vintage 1950S Criss Cross Halter Rita Flare Dress In Navy At Nordstrom, Size Large
Nordstrom
$123.00
Unique Vintage 1950S Criss Cross Halter Rita Flare Dress In Navy At Nordstrom, Size Large
Nordstrom
$110.00
Unique Vintage Sweetheart Midge Swing Dress In Black At Nordstrom, Size Large
Nordstrom
$110.00
Unique Vintage Sweetheart Midge Swing Dress In Black At Nordstrom, Size Large
Nordstrom
$123.00
Unique Vintage 1950S Criss Cross Halter Rita Flare Dress In Black At Nordstrom, Size Medium
Nordstrom
$123.00
Unique Vintage 1950S Criss Cross Halter Rita Flare Dress In Black At Nordstrom, Size Medium
Nordstrom
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Medium, Orange
Kohl's
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Medium, Orange
Kohl's
$50.99
Tweed Dress For Women Vintage 3/4 Sleeve Business Office Wear To Work Sheath Dress, Women's, Size: Large, Multicolor Blue
Kohl's
Free shipping
$50.99
Tweed Dress For Women Vintage 3/4 Sleeve Business Office Wear To Work Sheath Dress, Women's, Size: Large, Multicolor Blue
Kohl's
$123.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Black At Nordstrom, Size X-Large
Nordstrom
$123.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Black At Nordstrom, Size X-Large
Nordstrom
$132.06
$186.00
Victorian Ruffle Apron For Women, Historical Costume Pinafore, Handmade LARP Maid Apron Dress, Cottagecore Theater Apron, Custom Size Apron
Etsy
29% off
$132.06
$186.00
Victorian Ruffle Apron For Women, Historical Costume Pinafore, Handmade LARP Maid Apron Dress, Cottagecore Theater Apron, Custom Size Apron
Etsy
$160.00
Unique Vintage Square Neck Sleeveless Godet Swing Dress In Black At Nordstrom, Size Medium
Nordstrom
$160.00
Unique Vintage Square Neck Sleeveless Godet Swing Dress In Black At Nordstrom, Size Medium
Nordstrom
$65.00
Vintage Royal Hawaiian Knee Length Aloha Shift Dress
Etsy
322
Free shipping
$65.00
Vintage Royal Hawaiian Knee Length Aloha Shift Dress
Etsy
$148.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Pink Floral At Nordstrom, Size Large
Nordstrom
$148.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Pink Floral At Nordstrom, Size Large
Nordstrom
$123.00
Unique Vintage Reed Swing Dress In Black & Purple Floral At Nordstrom, Size Large
Nordstrom
$123.00
Unique Vintage Reed Swing Dress In Black & Purple Floral At Nordstrom, Size Large
Nordstrom
$98.00
Unique Vintage 1950S Poppy Flare Dress In Purple At Nordstrom, Size Small
Nordstrom
$98.00
Unique Vintage 1950S Poppy Flare Dress In Purple At Nordstrom, Size Small
Nordstrom
$123.00
Unique Vintage Shailene Pencil Dress In Green At Nordstrom, Size Small
Nordstrom
$123.00
Unique Vintage Shailene Pencil Dress In Green At Nordstrom, Size Small
Nordstrom
$48.00
$139.00
Women's Gothic Vintage Victorian Ball Gown Corset Dress - S, Blue
tohittheroad.com
65% off
$48.00
$139.00
Women's Gothic Vintage Victorian Ball Gown Corset Dress - S, Blue
tohittheroad.com
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Small, Pink
Kohl's
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Small, Pink
Kohl's
$225.00
1950-60S Vintage FLORAL FULL DRESS
Etsy
28
$225.00
1950-60S Vintage FLORAL FULL DRESS
Etsy
$123.00
Unique Vintage Prairie Swing Dress In Red At Nordstrom, Size Medium
Nordstrom
$123.00
Unique Vintage Prairie Swing Dress In Red At Nordstrom, Size Medium
Nordstrom
vintage dresses through the decades
0:48
vintage dresses through the decades
6 months ago
MSNGabi's Vintage (Video)
Goodbye Fast Fashion! Hello, Timeless Elegance: 4 Vintage-Inspired Outfits
0:23
Goodbye Fast Fashion! Hello, Timeless Elegance: 4 Vintage-Insp…
17.7K views2 months ago
YouTubeAiStyle
End of April 2025 #fyp #foryou #dressforwomen #trending #vietnamdress #saymecloset #vintagedress #incdress #pangsamba #graduationdress
End of April 2025 #fyp #foryou #dressforwomen #trending #vietn…
4.7K views9 months ago
TikToksaymecloset
I bought 100 vintage dresses
12:25
I bought 100 vintage dresses
134.7K viewsMar 1, 2019
YouTubeElise Buch
My 60s & 70s Vintage dress collection
My 60s & 70s Vintage dress collection
8.9K viewsFeb 27, 2022
YouTubeEmma Rosa Katharina
A Crossdresser's Life: Evening Gown
2:44
A Crossdresser's Life: Evening Gown
29.8K viewsApr 20, 2019
YouTubeA Crossdresser’s Life
Crossdressing - Cute polka dot dress
2:31
Crossdressing - Cute polka dot dress
55K viewsApr 16, 2020
YouTubeSierra Romeo
7:54
MEN should wear DRESSES | Crossdressing
40.8K viewsOct 27, 2020
YouTubeOlive La Strada
3:15
VINTAGE 1950's LOOKBOOK (Part 1) Party Dresses
77.4K viewsSep 24, 2020
YouTubeholistichabits
2:40
VINTAGE 1950's DRESSES: (Part 2) Lookbook
66K viewsNov 5, 2020
YouTubeholistichabits
6:42
My Favorite Dresses || Vintage & Reproduction
257.2K viewsMar 14, 2017
YouTubeRachel Maksy
5:00
Dressing up 1860's Style
684.8K viewsMar 20, 2008
YouTubeM. Z. Medenciy
15:49
I Dressed Like It Was 1967
5.7M viewsDec 31, 2017
YouTubeSafiya Nygaard
3:30
Getting Dressed in the 1920s - Eveningwear
1.7M viewsMay 3, 2019
YouTubeCrowsEyeProductions
1:44
Black and White 80's Gown
50.8K viewsFeb 20, 2009
YouTubeStephanie Marie Trans Southern Belle
0:12
TopVintage - 50s Cross Dress in Black
28.3K viewsMar 5, 2015
YouTubeTopvintage Boutique
18:21
Vintage Wardrobe Tour || 1910 to 1940's Dresses
11K viewsMay 12, 2020
YouTubeWith Love, Kristina
6:32
My FAVORITE Dresses||Vintage 1950's
120.3K viewsMar 12, 2018
YouTubeLaci Fay The Vintage Girl Next Door
5:18
100 Years of Dresses | Glamour
11.5M viewsNov 16, 2017
YouTubeGlamour
3:22
White 50's style prom dress - crossdresser
47.3K viewsDec 9, 2019
YouTubeVicky Blue
34:14
1950's Floral dress : Following V2960 : Pattern Review & Vlog
690.9K viewsJun 30, 2018
YouTubeAngela Clayton
4:53
Women's Fashion from the 1860's
157.5K viewsNov 27, 2010
YouTubeEsteem Education Co.
3:04
Crossdresser - Vintage sexy black dress
17.1K viewsDec 23, 2013
YouTubeSabryna Stella Tgirl♥♥♥
2:38
H&M Fall Fashion Haul: Crossdress Male to Female Transformation (pt…
100K viewsOct 16, 2020
YouTubeYoya Fabulosa
1:42
New Year and New Dresses (Crossdresser/Transvestite)
12.9K viewsDec 31, 2018
YouTubeClare
19:40
Making Dresses Out of Household Materials! || Recycle Retro
817.1K viewsMay 1, 2020
YouTubeRachel Maksy
6:21
Crossdresser Wardrobe: Look at All My Crossdressing Costumes. | Yo…
56.3K viewsOct 26, 2019
YouTubeYoya Fabulosa
4:09
Crossdresser wearing floral dresses for summer
59.3K viewsJun 24, 2021
YouTubeMel Cross
18:20
My Favorite Thrifted Vintage Dresses | 1940’s - 1980’s
5.5K viewsMay 14, 2020
YouTubeVicky Bermudez
0:55
Jessica wearing 1950s Style Halter-neck Dress (Crossdresser / Trans…
8K viewsApr 15, 2021
YouTubeJessica's Corner
See more videos
Static thumbnail place holder

Shop Crossdrossing Vintage Dresses

Sponsored
About our ads
$485.00
Stacees Vintage Bridal Wedding Dress Plunging V-Neck Ball Gown With Chapel Train
Stacees.com
$485.00
Stacees Vintage Bridal Wedding Dress Plunging V-Neck Ball Gown With Chapel Train
Stacees.com
$54.99
Floral Vintage Boho Maxi Dress
WAVLYNN
$54.99
Floral Vintage Boho Maxi Dress
WAVLYNN
$38.50
Cross-Over Midi Dress
WAVLYNN
$38.50
Cross-Over Midi Dress
WAVLYNN
$39.99
3/4 Sleeve 1950S Elegant Lace Floral Embroidery Swing Dress M Apricot
modernonlinemart.com
$39.99
3/4 Sleeve 1950S Elegant Lace Floral Embroidery Swing Dress M Apricot
modernonlinemart.com
$32.38
$49.19
Vintage Elegant Women's 1920S Party Dress With Sequin Embroidery, Form-Fitting Patchwork Tassel Boat Neck Bodycon Cocktail Dress Flapper Dress Great Gatsby Dress 20'S Vintage Thanksgiving Women Outfit Black Homecoming Dress C
shein
34% off
$32.38
$49.19
Vintage Elegant Women's 1920S Party Dress With Sequin Embroidery, Form-Fitting Patchwork Tassel Boat Neck Bodycon Cocktail Dress Flapper Dress Great Gatsby Dress 20'S Vintage Thanksgiving Women Outfit Black Homecoming Dress C
shein
$36.99
$69.99
Women Retro Dresses Vintage 1950S Short Sleeve Prom Rockabilly Swing Dress - L, Yellow
tohittheroad.com
47% off
$36.99
$69.99
Women Retro Dresses Vintage 1950S Short Sleeve Prom Rockabilly Swing Dress - L, Yellow
tohittheroad.com
$150.00
Stunning Rare Ramona Rull Vintage 1960'S 1970'S Bohemian Embroidered Kaftan Dress
Etsy
439
$150.00
Stunning Rare Ramona Rull Vintage 1960'S 1970'S Bohemian Embroidered Kaftan Dress
Etsy
$17.33
$26.89
Red Off-Shoulder Mesh 2In1 Trumpet Sleeve Long Sleeve Women's Dress,Western,Vintage,70S,The Bachelorette,Christmas,Red Dress,Christmas Dress,New Year Dress,M
shein
35% off
$17.33
$26.89
Red Off-Shoulder Mesh 2In1 Trumpet Sleeve Long Sleeve Women's Dress,Western,Vintage,70S,The Bachelorette,Christmas,Red Dress,Christmas Dress,New Year Dress,M
shein
$35.99
Belle Poque Women's Vintage Square Neck Dress 2026 Summer Short Sleeve Layered Tiered Ruffle A-Line Swing Midi Dress
Amazon.com
603
Free shipping
$35.99
Belle Poque Women's Vintage Square Neck Dress 2026 Summer Short Sleeve Layered Tiered Ruffle A-Line Swing Midi Dress
Amazon.com
$115.00
Vintage Floral Dress Puffy Sleeves Cottage Core Dress Prairie Dress 1920S Victorian Edwardian Dress Floral Pattern Pastel Floral Print Roses
Etsy
444
Free shipping
$115.00
Vintage Floral Dress Puffy Sleeves Cottage Core Dress Prairie Dress 1920S Victorian Edwardian Dress Floral Pattern Pastel Floral Print Roses
Etsy
$135.00
Vintage Late 60S Psychedelic Tori Richards For I Magnin Hawaiian Maxi Dress
Etsy
930
$135.00
Vintage Late 60S Psychedelic Tori Richards For I Magnin Hawaiian Maxi Dress
Etsy
$185.00
Unique Vintage 1950S Sweetheart Swing Dress In White Cat Print At Nordstrom, Size Medium
Nordstrom
$185.00
Unique Vintage 1950S Sweetheart Swing Dress In White Cat Print At Nordstrom, Size Medium
Nordstrom
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Large, Green
Kohl's
$42.99
Women's Summer Boho Floral Print Dress Vintage Square Neck Ruffle Swing Flowy Beach Long Maxi Dress, Size: Large, Green
Kohl's
$75.99
Women's Vintage 50S Dress Cocktail Sleeveless Square Neck Midi Floral A-Line Dresses, Size: Large, Beige
Kohl's
Free shipping
$75.99
Women's Vintage 50S Dress Cocktail Sleeveless Square Neck Midi Floral A-Line Dresses, Size: Large, Beige
Kohl's
$230.00
Colonial 18th Century Dress Cotton Historical Day Gown Floral
Etsy
1K+
Free shipping
$230.00
Colonial 18th Century Dress Cotton Historical Day Gown Floral
Etsy
$153.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Blue Sky, Floral At Nordstrom, Size Small
Nordstrom
$153.00
Unique Vintage 1950S Sweetheart Sleeveless Swing Dress In Blue Sky, Floral At Nordstrom, Size Small
Nordstrom
$160.00
Unique Vintage 1940S Sweetheart Button Front Swing Dress In White Lady & Tramp Print At Nordstrom, Size Medium
Nordstrom
$160.00
Unique Vintage 1940S Sweetheart Button Front Swing Dress In White Lady & Tramp Print At Nordstrom, Size Medium
Nordstrom
$120.98
Womens Vintage V Neck Ruffle Split Bridesmaid Party Long Dress, Women's, Size: Medium, Red
Kohl's
Free shipping
$120.98
Womens Vintage V Neck Ruffle Split Bridesmaid Party Long Dress, Women's, Size: Medium, Red
Kohl's