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How I Find Dresses That Work


Recently, I bought a dress in a small, mom & pop boutique. It is tricky to buy a dress for a tall or oddly shaped body. I fit in both categories. I am 6 feet 3 inches tall (1.9m) and I have broad shoulders and narrow hips. “It’s hard to buy clothes because I have my father’s hips.” I had to remember all of the things I have learned about dress buying. I decided to record my knowledge here. Maybe this will be useful to someone else!

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Grocery Shopping in a Dress


It has been a LONG time since I have had an outing!

I arranged with my wife to go on an outing and do our grocery shopping. I wore my black dress with colorful angular patterns, a black cardigan, nude pantyhose, and black strappy flats. I also wore a black mask. I love being able to wear a dress!

I did not get a picture of my original outfit. There is a picture of the dress and cardigan I wore in this post.

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A Long Forgotten Confession


I remembered something today. Years ago, when I was in college, I begrudgingly confessed to trying on women’s clothes. I had to confess in front of a group of my peers and strangers. It led to a conversation later with my peers.

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Happy to See Me?


Where I used to work, there was a nearby Mexican restaurant that was my favorite. I went there once or twice per week (in menswear) and I always ordered the same thing. All of the staff grew to recognize me. They would greet me when appropriate. One time, I heard a waitress (let’s call her “Miss B”) tell another staffer that “Un taco suave” was here. They knew me.

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Short Outing


I finished up at work a little early. I put on a dress and visited a consignment store that I have not been to in a long time. I wore my patterned dress, black cardigan, and wedge sandals.

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Denim Skirt Day


I had a day to get some things done. I did it in a skirt! I wore an above-the-knee denim skirt, purple top, purple mask, beige cardigan, and white sneakers. I felt pretty good about the outfit, but I worried about the colors some.

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Grocery Shopping in a Skirt


I have not had a chance to go out while dressed pretty in one full month. I have barely left the house in ANY form of dress in one full month!! I went grocery shopping today and I wore a gray skirt, a black/white/gray patterned top, and my wedge heels. I also wore a light red layer under my top.

The store was busy, but no one minded the dressed up man.
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Pandemic vs. Crossdressing


I have avoided discussing the COVID-19 pandemic on my blog.  I guess I just was not interested in going there…  Being locked in at home has had a profound impact on my opportunities to go out and wear something pretty.  I assume that I am not the only crossdresser who is feeling this.  This is tough.

My wife knows that I am a crossdresser.  She does not love it.  She does love me.  Sometimes, I will wear a skirt or dress in the evening after our kids (who do not know that I crossdress) are in bed.  Dressing like this is not particularly pleasant.  I feel awkward about dressing up very much, so I will wear a T-shirt with a skirt while barefoot, or something limited like that.

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Crossdressed Grocery Shopping


Recently, I bought a new beige cardigan.  I have wanted a beige cardigan for a long time.  It is beautiful.  I just had to wear it… and we are running low on food… So, I went grocery shopping while dressed pretty!  I wore my beige/khaki-colored cardigan, my striped top, a black skirt, and my black flats and went on an outing.


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Running A Few Errands While Crossdressed


I needed to go across town to take care of some business, so I crossdressed for part of my outing.  I wore a beige skirt, a navy top, a white cardigan, and brown wedge heels.  I felt pretty.  This is the first time that I ever put this outfit together.


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