Wednesday, November 29, 2023

Stuff 20: What to Wear?

By J.J. Atwell

Hello All

JJ is back with more stuff!

This being Stuff #20 I thought it might be time to say again that I’m simply writing about things from my perspective. I don’t claim to be an expert in the subjects and I’m sure people will find things they agree or disagree with. I only hope reading my Stuff gives you something to think about. I’d be happy to read all of your thoughts. My contact info is at the end.

Dressing for the Occasion

We crossdressers often face the same dilemma that genetic girls face: what to wear. To some extent, our decision is easier since most of us have a smaller selection of clothes in our closet than most women. And maybe having more stuff just makes the decision harder because there are more choices.  

It’s probably obvious to all of us that deciding what to wear depends on where we are going. If we are staying home, our clothing choice isn’t that difficult. Whatever is clean and comfortable will do. Perhaps, just a pair of leggings, a loose top and sandals or slippers would be perfect for a stay-at-home day.  

Things get a bit more complicated when going out. Especially for crossdressers who want to dress to “blend in” with the general female population.  Just like a genetic girl, a crossdresser should think about where they will be. Is it a place where women typically get more dressed up? Or is it just a trip to the supermarket?  

Going to a special occasion? Maybe a holiday party? I’m currently thinking about what to wear to my group’s holiday girls’ night out in a couple of weeks. I know from past meets that the members will be dressed in a range of outfits from simple holiday tops to fancy dresses.  My closet is a bit lacking in both choices, so I’m doing a bit of online shopping right now.  The meeting is at a local restaurant that I have been to before and know it’s not really a dressy kind of place. So I narrowed my search down to nice holiday tops that I can wear over skinny jeans. I’ll accessorize with some holiday jewelry borrowed from my wife. Stuff like that should work for this venue.

I’ll be back

Hope you have fun thinking about what to wear. Until then, I’d welcome comments here on the blog or by email at Jenn6nov at-sign gmail dot com. 

Source: Cynthia Rowley
Wearing Cynthia Rowley

Poodle skirted!
Poodle skirted!


  1. Hi JJ, Congrats on stuff #20! They've all given me "stuff" to think about. As a stay-at-home CD, I (unfortunately) don't experience that real-life what-to-wear dilemma. But that doesn't mean I don't think about it! In every occasion in my life...whether I'm grocery shopping or out to dinner or biking or in the office...I imagine what feminine outfit I would wear, fussing over the tiniest details of undergarments and accessories. I know it's not the same, but it sure is fabulous to play "what if"😍

    1. Thanks Elise, JJ here. I'm glad you found something of interest! Before my first time out I thought long and hard about what to wear. In fact, I'm going out on Saturday night and I've been pondering what to wear for over a week now. Did some last minute shopping so I've got an essentially new outfit for the occasion.

    2. Hi JJ, In my land of make believe, I have unlimited access all the feminine clothes, shoes, and accessories my heart desires...but I can imagine in the real world it's much more challenging acquiring all the necessary items to look your feminine best. (I had a hard enough time finding a tie for a drab outfit recently haha.)

      Have a fabulous time at your Saturday occasion!

  2. On another site there is a lot of bantering back and forth as to "blending" with those humans around you. I'm a "dresses only" girl and do not own a single pair of women's pants; jeans, shorts or other. I just cannot wrap my head around wearing clothing that has been co-opted from the men's side of the department store. I am not comfortable mingling with fellow humans, so the issue becomes how do I not stand out in a dress when taking an evening stroll when the vast majority of the women are wearing pants; not a dresses and heels. On my evening strolls in a safe neighborhood there are two 24 hour grocery store. I carry a tote with the logo of one of the stores, so it appears I am a woman coming home from a day's work in an office; knee length dress and a black wedge of my feet. I do have a good number of long dresses that are appropriate for semi-formal or a holiday party but there are no CD social groups in my area, sigh!

    1. JJ here. I appreciate your comments. Sounds like you've worked out a good solution to blending in. Thanks for taking the time to share.