How long did it take to get over feeling embarassed wearing proper clothes

[Dani]

The very second I found a size that fits! 

[JoanneB]

If I start counting from my first experience dressing properly it took 40 years.

Oh I Love and hate your questions....

My first time "dressing properly" I was 4 years old. Mom had a different opinion. it took another 50+ years, and 2 utter failed transition experiments before the "This is Really ME" moment some 50 years later.

On the Other Hand.... I was, have been, and still am.... "Dressing Properly" In accordance with what believe I should. What matters most is what I see when I look in the mirror.

[Brooke]

I stopped being embarrassed and self conscious when I successfully created relationships with people who never knew me as male. Felt if I can do that, I don't really have much to worry about


Hugs,
~Brooke~

[Denise]

I have never felt embarassed about wearing the proper clothes ever since I started coming out.  I do feel nervous and am extra vigilant when I am out and about in case a hater takes exception to my existence.  But not embarassed.  I dress well and look good.

I agree. Nervous at times.

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[Ataraxia]

Pretty much after the first time. I was really really really nervous and was primed for someone to look at me weird or clock me. It didn't happen, nobody even looked twice at me. Everyone just went about their business and even gendered me female pretty much 100% of the time. So I no longer felt like I was constantly the center of attention. Realizing that no one is sizing you up or evaluating you constantly (except for yourself, of course) goes a long way towards feeling less self-conscious.

[Mariah]

Definitely this. I was never embarrassed but yeah definitely self conscious the first few times out.
Hugs
Mariah

A little self-conscious the first few times maybe but never embarrassed.

[AnneK]

In the beginning yes.. well not embarrassed but more nervous. I remember the first time I went out in public dressed as a woman it was a very nervous experience, but also exhilarating.

I had the same experience when I started cross dressing.  I was very nervous going out the door, but eventually I got over it.  These days, while not fully cross dressed, I openly wear pantyhose with shorts as as well as nail polish.  I don't know if anyone has noticed my bra.  It's just something I consider to be completely normal for me.