Is this crossdressing, underdressing, overdressing or just plain dressing?

A few weeks ago I wrote this article in which I explored what was in fact crossdressing and what was not crossdressing. I questioned whether you could be crossdressing if you were wearing women’s clothes that were not obviously women’s clothes?

I had never before been confronted with this issue personally as I am an ‘all or nothing’ kind of girl. Either I dress fully en femme, or I do not dress. However, my wife has been suggesting that I spruce up my drab wardrobe and she has also been hinting that she finds the androgynous look very attractive. So I decided to see what I could do.

On a recent online shopping expedition I saw these boots:

These boots are gonna walk all over you
These boots are gonna walk all over you

I have never before owned a pair of cowboy boots but I have always thought they were pretty cool. These are very definitely women’s boots, but having looked at them I thought that I could probably carry them off in either mode. They would look awesome with the denim mini, skinny jeans etc en femme and could also work with jeans in male mode. Being able to wear them in either mode made it very easy for me to justify the purchase.

I bought them and when they arrived last week I tried them on with my jeans and they worked. Cowboy boots for the win! I decided to wear them (in male mode) to a music concert last night (apart from the boots I was in full male mode). Now, to the practiced eye, they are very definitely women’s boots. The foot is narrow and is made to accentuate the slimness of the foot ( a look I happen to like), the heel is a bit higher than usual on men’s shoes, the pattern is more feminine and the leather softer than on men’s boots I have seen. But short of a very intense investigation I think they ‘pass’ as men’s boots (especially as I wore my jeans over the boots hiding the more feminine parts).

I am not entirely sure how I feel about this. Is this a rather strange form of underdressing? Was it crossdressing at all? Or was I just dressed in a manner (mostly) of my choosing expressing the feminine side of my character as best as I was able?

The more I think about it the more I feel that it is the latter. I have an item of clothing that I like, that is comfortable (they are in fact the most comfortable boots I own) and that expresses who I am very well (apart from me not actually being a cowboy that is). It was interesting to be out and about in a very visible item of women’s apparel and yet ‘fly under the radar’ so to speak. I am looking forward to wearing these with that denim mini though.


Add yours →

  1. Ignoring the whole crossdressing, underdressing part maybe you said what really matters the most. The boots express who you are really well. Isn’t that what matters when we dress is that we dress in a manner that we feel reflects us and we are comfortable with wearing?

    Liked by 2 people

  2. One of the great gifts of being a crossdresser is an enhanced ability to express ourselves through our wardrobe! When I first started, it was like suddenly having permission to be interested in clothes and colors and style! Even if you only capital-D-dress a small amount of the time. It’s fun to wear cute clothes, and that’s really all that matters!

    Liked by 2 people

  3. I love your cowboy boots. Next you should get some rhinestone cowgirl boots, you never know when you might need those. In fact, now I wanna get some.

    Liked by 1 person

  4. One of my favorite pair of jeans is stretchy low rise boot cut womens jeans. Even in male mode, I love the way my ass looks in them, they are soft, move with me, etc. I have with them to work on many occasions, and all that happens is I get flakk about how uncomfortable skinny jeans are. And they are right, if they were ‘male’ pants. Little do they know that they are not a size 34×32, but about an 8 =)

    Liked by 1 person

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