Cute crossdresser in the snow

After a HalloweenΒ hiatus, crossdressed outfit of the week is back, and I’ve got some great crossdressing fashion ideas to share with you. Β 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 πŸ˜‰

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.


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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14 years ago

Lovely combination there, though I prefer a pointier toe on the boots myself πŸ™‚
As for the appology… Sometimes there just is not the time to do what you want to do everything that you want to, no appologies required πŸ™‚

14 years ago


14 years ago

This is a really neat site…..glad i found it …all you gals have great ideas

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