Crossdresser doing another modeling of 1950’s “Dating Dress”
2:40
Crossdresser doing another modeling of 1950’s “Dating Dress”
7.9K viewsDec 5, 2020
YouTubemdolivetti
Crossdressing a Retro Look – How to Crossdress in Vintage Style from Start to Finish!
5:31
Crossdressing a Retro Look – How to Crossdress in Vintage Style fro…
14.1K views7 months ago
YouTubeCrossdressing Lifestyle
Getting dressed in the 1950s
0:56
Getting dressed in the 1950s
6.7K viewsSep 21, 2022
YouTubesew_through_time
White 50's style prom dress - crossdresser
3:22
White 50's style prom dress - crossdresser
47.3K viewsDec 9, 2019
YouTubeVicky Blue
Crossdresser modeling 1950's style dating dress on first day of 2024
2:11
Crossdresser modeling 1950's style dating dress on first day of 2024
5.9K viewsJan 4, 2024
YouTubemdolivetti
Crossdresser: 50s Style dress
1:31
Crossdresser: 50s Style dress
9.7K viewsSep 3, 2023
YouTubeIsabelle Labelle's Fashion
1950s Housewife Dresses and Purpose
21:06
1950s Housewife Dresses and Purpose
79K viewsSep 7, 2021
YouTubeNina Dream
8:03
1950s Style - What Women Wore in 1950s America
350.2K viewsFeb 1, 2023
YouTubeThe History Lounge
1:13
50s Dress Crossdresser
4.2K viewsSep 17, 2021
YouTubeTrixy Deans
8:03
The Shocking Truth About These Famous Crossdressers!
7.3K viewsApr 6, 2023
YouTubeAbout TG Life
6:52
Crossdresser: 50s Style putting on stockings, petticoat and gloves
14.6K viewsJul 22, 2023
YouTubeIsabelle Labelle's Fashion
26:14
Gender in Fashion & Costumes: A History of Crossdressing [CC]
8K viewsAug 20, 2021
YouTubeLizCapism
0:21
Getting Dressed in the 1950s
8.9K viewsFeb 6, 2021
YouTubeOlga Kurzova
0:55
Jessica wearing 1950s Style Halter-neck Dress (Crossdresser / Trans…
7.5K viewsApr 15, 2021
YouTubeJessica's Corner
0:12
TopVintage - 50s Cross Dress in Black
28.1K viewsMar 5, 2015
YouTubeTopvintage Boutique
4:10
Stylish & Bold: Watch a Crossdresser Shine in a Vintage R…
10.7K views11 months ago
YouTubeCrossdressing Lifestyle
1:25
Fifties Fashion (1950s) - Archival - BBC Motion Gallery
4.8K viewsSep 17, 2014
YouTubeGetty Images
7:36
Vintage Outfit for crossdressers part II
59.6K viewsAug 20, 2020
YouTubeMiss Cookie Monster
2:40
In Style: Parisian Fashion (1950s) | Vintage Fashions
195.5K viewsMar 7, 2012
YouTubeVintage Fashions
3:02
Clothes Make the Man
Apr 10, 2014
NY TimesPatrick Healy
9:44
50 Glamorous Photographs Showing Dresses That Girls Often …
19.6K viewsJun 17, 2022
YouTubeYesterday Today Tribute
3:06
50's Swing Dress Lookbook
129K viewsNov 14, 2016
YouTubeSarah Louise Porter
6:05
Classic pinup outfit idea for crossdresser
63.1K viewsJul 14, 2020
YouTubeMiss Cookie Monster
0:12
Jasmine Chiswell on TikTok
14.4M viewsJun 20, 2020
TikTokjasminechiswell
22:08
I Tried Every Iconic 1950s Look in 48 Hours | Glamour
976.8K viewsJan 31, 2019
YouTubeGlamour
0:46
Tanya Melody (short 59) Crossdressing fashion - Vintage s…
3K viewsAug 24, 2023
YouTubeTanya Melody UK
10:19
Fashion of the 1950s | Men's Fashion
34.5K viewsMay 7, 2019
YouTubeRetro Azul
5:14
1950s Housewife looks - Genderfluid Demigirl
3.5K viewsJan 5, 2023
YouTubeemily shadows
11:15
Fashion House (1950-1969)
116.1K viewsApr 13, 2014
YouTubeBritish Pathé
See more videos
Static thumbnail place holder