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Brief Outing While Dressed Pretty


I “needed” to get out and wear something nice. During my lunch break, I wore a black skirt, a beige blouse, and a black cardigan with my black wedge heels. I also wore a chunky necklace that I bought in a recent outing. Today’s outing was small. It was a beautiful day to be out and about. I had a couple interesting encounters.

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A Day Visibly Crossdressed on TDoV


Today was the Transgender Day of Visibility (TDoV). I do not call myself “transgender” because I do not change my gender when I am crossdressed. BUT, close enough. Each year I try to do my part on the TDoV. We can call it CDoV just for me…

For my outfit, I followed Hallie Abrams’ fashion advice from her blog, The Wardrobe Consultant. She introduced me to The 2 Out of 3 Rule. This rule is a rule that a low-fashion dude like me can handle! Wear two garments of one color and one garment of a bold, different color. I wore a black top, a black skirt, black flats, with a cardigan in deep red. I felt very well put together. Thank you Hallie!

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Vaccinated in a Dress


A couple weeks ago, Stana, posted on her blog at a post named “Passing in the COVID-19 Vaccine Line“. I read that title and I was hooked on the idea of wearing something pretty to my vaccine appointment!

I wore my black dress, nude pantyhose, black wedge heels, and a black sweater duster with brown accents and decorations. As always, I presented male.

If you squish your arm into your side, you look like you have taken
better care of yourself than you really have!
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I Crossdressed Where I Am A Regular Customer


There is a Mexican restaurant near where I work. I get my lunch from there roughly once per week. I have been doing this for years. I have considered, on a few occasions, going there while dressed pretty. I never did because I might go there later with co-workers, and because this restaurant is rather busy. I have encountered people at this restaurant that I know from other aspects of my life. Therefore, I have not gone there dressed pretty. Until last week, that is…

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I Donated Blood While Crossdressed


It was ten years ago, perhaps longer, that I tried to donate blood while “crossdressed”. Then, I wore some white pantyhose with no socks under my men’s pants. I do not remember if I had on ladies’ sneakers or men’s. I was very nervous, and it showed in my vitals. I was refused. This week, I finally built up enough courage to try it again. This time I wore my black dress with gray brushstroke print. I did it!

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Crossdressed on a Road Trip


Recently, I went on a 2-hour drive to a funeral. After the funeral, some of my family visited together and caught up. We finished up around lunch time. For my return trip, I had some time to have a crossdressed outing, I brought an outfit that would have been appropriate for a funeral for my return trip. I had my black/white/gray printed blouse, black knee-length skirt, black pantyhose, a red mask, and black wedge heels.

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Another Outing Doing Errands


I left work early for lunch so I could dress pretty and take care of some errands before there was a crowd of other lunch-goers. I wore my brown and black skirt, black opaque tights, my new green sweater, and black wedge heels.

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Errands in a Skirt


I checked my blog recently and I saw that someone had left a comment 18 days before. I knew it had been a while since I had last logged on, but that was a bit of a surprise. That means it has been even longer than that since I last wore something pretty in public (or in private). I have been avoiding going out in public unnecessarily for so long that I have almost forgotten that I am a crossdresser!! I needed to run a few errands. I decided to do it while dressed pretty (at least for part of the time).

I packed my khaki skirt, a purple top, and a white cardigan with nude pantyhose and black flats. I also brought some men’s shorts.

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One Last Christmas Shopping Outing


I needed to buy one more Christmas gift. I decided I would do it while dressed pretty. I wore my new gray and black, printed dress, a black cardigan, and my strappy gray heels.

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One Size Fits All?


I felt like wearing something pretty under my clothes one day. I thought, “I almost never wear opaque tights. I will wear some tights so that I am not wearing out my favorite hose.” I selected one of the few pairs of black opaque tights that I own. What happened next amused me quite a lot.

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