Tags: crossdressing fashion

Crossdressed Outfit of the Week: Here Comes The Snow

Comments: 8 Comments
Published on: November 7, 2009

After a Halloween hiatus, crossdressed outfit of the week is back, and I’ve got some great crossdressing fashion ideas to share with you.  While I dearly love browsing for a cute skirt, or the perfect top to complete my outfit I’m sometimes frustrated with not being able to find my size. Crossdressed Outfit of the Week features clothes that at the time of writing are available in at least size XL (or 16/18) and shoes available in 11W or larger.

Crossdressing in the Snow

Crossdressing fashion: A mid-length skirt

Crossdressing fashion: A mid-length skirt

Fall and Winter fashions are a crossdresser’s dream come true. Gone are the short breezy skirts and skimpy tops that all but scream masculine at your too broad shoulders. One of my fall favorites it the mid-long skirt paired with a good pair of boots. In the fashions shown here the floral skirt (on special at almost $55 off the original price now) has a femininity about it without sporting too small a floral pattern. As you know, small patterns make you look even larger – not something any girl wants ;)

A Crossdressers Favorite: High Heel Boots

A Crossdresser's Favorite: High Heel Boots

I love shoes of all types, but I have a particular fondness for boots. My favorite are ankle boots, though in Northwest winters ankle boots will leave your legs cold and wet. This week’s crossdressed outfit features a stylish mid calf leather boot. I’m trying hard to resist buying this one (I just sent back a pair of boots that didn’t quit fit, but even then my lovely wife is looking at my growing shoe collection with … concern).

Have fun with the last few weeks of fall while the remaining few leaves cling to the trees and the snow is held at bay.


P.S. I apologize for being a bit quiet these last few weeks. Between work, family drama and home projects it’s been a bit tricky to do one of the things I love the most – spending time with the lovely ladies at Crossdresser Heaven.


Socially Acceptable Cross Dressing – will it ever be in style?

Fashions are a funny thing, and crossdressers are perhaps more beholden to the whims of the fashion fairies than most men. When men dress in women’s clothes, there is something special about looking fabulous and beautiful.

The other day I was thinking – what if crossdressing was normal? You know, if you were just as likely to see a man in high heels and a skirt as a woman wearing a pantsuit. What is there was no masculine gender expression, no feminine gender expression. Would we still be crossdressers? In fact, would we still have the desire to crossdress?

Certainly there must be some part of the transgender experience which is about being unique, in our expression of who we are – the desire to be like woman, yet still knowing that we are a man.

Don’t tell crossdressers they’re normal

If you do, we just might agree. Many organizations, such as Tri-ESS, go to great lengths to remove the stigma from crossdressing. This stigma is entirely a social construct, created by our culture. There are theories as to why crossdressing is taboo – perhaps on a subconscious level it slows down the acquisition of a suitable mate with which to propagate the species?

Nevertheless, fashion will move forward. The brief rise of the metrosexual in the mid 2000′s was a definite step towards a more socially acceptable way for men to express their femininity. Even if all it really meant was that you wore nice clothes and bathed more than once a week.

Socially Acceptable Cross Dressing

I wonder if the next fashion wave will see crossdressing as desirable and trendy? I hope so, but I’m not going to leave my skirt hanging in the closet waiting for it to happen…


P.S. Don’t wait for crossdressing to come in style. Learn how to do your makeup like a professional and look fabulous!

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