Favorite Crossdressing Outfits

As some of my readers will know, my boyfriend is a cross dresser and I asked him what would be his dream outfit if he could choose anything he wanted. Some that he mentioned were bridal gowns with lots of layers of tulle, the sissy style dress with a full petticoat and the fishtail style evening dress again with a bouffant fishtail. He picked out the photo below as one of his favorite (pity its so expensive cause I'd REALLY like to see him in that).

Now I bet you noticed a recurring pattern as I did: full skirts with bouffant style slips. After surfing around on the subject I think it does seem that crossdressers often have a preference for very full dresses that you might only wear as a bride or princess costume. Actually, many of those favorite outfits are something that women are hardly ever going to wear these days anymore. Many seem like something from the past, when women were dressed very feminine. Others like the sissy dress seem more like something that little girls might have worn rather than adult women.

Does anyone know why this is? My boyfriend said “because they’re the most feminine”. So do cross dressers always go for the most feminine outfits they can think of? He certainly does. I suppose it makes sense if you think of femininity as something that crossdressing men crave to have and to express.

photo from www.ellyannausa.com

One thing I read into this is that cross dressers don’t just want to imitate girls or dress like them (because most women hardly ever wear anything like the kind of outfits my boyfriend describes). So it's a kind of compensation for the mega strict masculine dress code (i.e. anything not-feminine). This craving of femininity is very common among cross-dressers I'm told and it makes even more sense if you imagine that you’ve never been allowed to experience anything feminine your entire life. I suspect there can be even more to it which is what I wrote in my article on the sissy dress.

To me it doesn’t matter really. I’m just trying to understand the minds of these intriguing people. I guess I’m fascinated with the gender bending nature of cross dressers. How they provoke you into redefining your ideas of feminine and masculine behavior and, not at last, how they look so beautiful and vulnerable that you want to just have them for breakfast – or before.

So I'm curious what others think about how and why cross-dressers tend to want to wear super feminine outfits with lots of frills and ruffles? Please share your opinion with us.

There's now a kind of follow up to this article where I go more into detail about the various outfits.

And other CD related outfits here:

Male Corset

Dresses for Men

Men in Tutus

Men in Petticoats

Sissy Panties

Sissy Maid



Add comment

Security code

We use cookies to improve our website and your experience when using it. Cookies used for the essential operation of the site have already been set. To find out more about the cookies we use and how to delete them, see our privacy policy.

I accept cookies from this site.

EU Cookie Directive Module Information