Crossdressed Outfit - Conservative Trendy

I’m starting a new feature here at called the Crossdressed outfit of the week. Every Friday I’ll put together an outfit that will not only look fabulous, but actually fit those of us whose proportions are somewhat larger than the typical woman.  All shoes will be available in at least 11W, and clothes will be available in size 18-20, or extra large.

This week’s outfit matches a conservative white embroidered poet sleeve tunic shirt with an olive detail skirt and brown leather 2 inch pumps. The detail on the skirt will add some flare to your conservative look. The outfit will be well complemented by a wide belt, and tan pantyhose.


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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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Joanna Phipps
Joanna Phipps
14 years ago

While I love to see all of the uber cute outfits that grace the pages of this site I cannot help but be a little bit jealous of those who fit in something under an 18-20w. I seem to have been graced with the body of a line backer and feet to match. I am 6′ 2″ and about 250 (yes I know I shouldn’t discuss my weight), and size 11w to 12w feet. This has made is a dickens of a job for me to get a good set of heels (or nearly anything else for that matter ).… Read more »

13 years ago

I really like this skirt and blouse combination. Feminine, without being "over the top". The brown pumps really set it off nicely, too. I would want the handbag, shoes and belt to match one another for both grain and color.

Were it me, I would wear slightly darker, but still sheer hose, and nude undergarments and garter belt. (I don't wear pantyhose, because the waist cuts in. after a couplke of hours. As my wife used to say, "I hate pantyhose. The waist just keeps getting smaller and smaller, all day long!")

7 years ago

hola amigas me ha encantado toda la informacion que he recibido y lo aprobechare al maximo ,gracias por todo

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