Crossdressed Outfit of the Week: Here Comes The Snow

Cute crossdresser in the snow

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.

  1. Marsha 6 years ago

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

  2. MELONY 6 years ago


  3. Stacy 6 years ago

    Lovely combination there, though I prefer a pointier toe on the boots myself :)
    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 :)

    • Profile photo of Vanessa Law
      Vanessa Law 6 years ago

      Thanks for your understanding Stacy. Here’s to boots of all shapes and sizes

  4. Lesll 6 years ago

    I enjoy winter outfits. I like the long skirts and sweaters and jeans and etc and etc.Its just fun to keep changing ones outfits all the time. I like the challenge of constantly looking for new things to wear. Its so easy to become a shopaholic if money was no constraint.I do like that outfit combination of a long skirt and boots.,,,,,,,Here I go again.

  5. Profile photo of Vanessa Law
    Vanessa Law 6 years ago

    haha – at least we’re not alone in our appreciation of shopping 😉


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