My Clothing Journey

[Note – what I describe of myself should not be taken as prescriptive. It does not seek to defend femininity as necessarily being an aspect of having a female gender as I am aware that not all who have a female gender have any necessary connection to femininity as such. Think of what is usually portrayed as tomboys, although I feel this is a misnomer seeing how these girls and women don’t identify as male. What they do is take on gender expressions and roles that are more often found in men. You can also find the opposite with boys and men. Here society is much more likely to find fault and bullying can result. Or, other demeaning actions.]

Initially, this was to be a part of a larger post on things I didn’t expect at the beginning of my gender journey, and have since come to pass (Things I Didn’t Expect). In that post my love for clothes came first in thought. After which I got the idea for this separate post because I had found it lengthening beyond the bounds of that post.

My interest in clothes has increased vastly since transitioning. I will write about what I could call my clothing journey. This is because, like my gender, how I dress has change, and many will perceive of their transition as a gender journey. There has been a program called Gender Journeys created by Gender Illumination. I was in this program as a mentor. But, it also included workshops dealing with social issues in an intersectional approach as well as affinity groups and fun nights.† With that aside let me begin.

Back when I lived my life as a guy unaware of my female gender I had a very basic clothing routine. I rotated wearing several pairs of different colored jeans never wearing the same color two days in a row. In warmer weather I wore colored t-shirts of various color, and in the colder months I wore sweat shirts. My only rule at that time besides rotating colors was that they were clean.

While I knew my clothing choices would change, the degree to which they have, and the relationship I have with clothes in general began to change upon transitioning in July of 2019. Prior to this, but after I recognized myself as a woman, I had an assortment of sexy (some downright slutty) clothing attire. I had quite a few high heels and stockings and panties (mostly thongs). But, upon transitioning I gave up dressing in this way. I never went out dressed as such, anyway. Afterwards, I only wore my heels twice when going out on one of my transversary celebrations with my partner, Bette. Hosiery (mostly tights to avoid runs) I now wear only when they have a function, such as dressing in colder weather, if not to cold to wear a skirt. They come off when I return home, just like my bra, which I feel necessary to wear out of modesty. Okay, I will admit they do enhance my breasts’ appearance. Both of these items I thought I would wear all day long if I could. Not so anymore.

At first I went with a more unisex look. I got three different colored pairs of Gloria Vanderbilt jeans, three women’s active t-shirts, two pairs of shorts, and two sports bras. This was in July/August; when the weather started to chill I got a couple of pairs of leggings. I mostly wore these things until mid-fall. While others could not tell, or most people anyway, a neighbor child did, but as far as I know she was the only one.‡

How did things change in mid-fall? The first thing was I went to a Goodwill thrift store and did some women’s clothes shopping: I browsed, I tried things on, and I purchased a number of items. Even though I was in an unisex outfit, I was still clearly a male shopper. But, I did not shop like one. I shop like most other women I have seen clothes shopping. My behavior match the feminine more than the masculine way.^ I went with my partner, Bette. I showed her each item I tried on as see sat on a sofa. I don’t know how many of them I showed her, but I purchased six of them. These were two blouses, two skirts, a pair of dress slacks, and a jacket. All, but one top were obviously feminine in appearance.

I believe I went back several times before the covid-19 pandemic developed. I also went at least twice to another thrift store I use to by books at. One day (in December 2019) I went in and saw a knit dress that I fell in love with (never remember doing that before) and which is still my favorite. I left, but came back the very next day and bought it with another dress and a skirt. I was so excited I took Bette out to dinner fully presenting as a woman (wig, dress, pantyhose, and booties) for the first time to a nearby sushi and hibachi buffet.

I went full time presenting as a women after the new year. I have gone to a Nordstrom Rack a bunch of times, but rarely did I buy anything. But, I got my favorite booties there—a pair of Doctor Scholl’s with about a 1.5 inch heel coming up to the ankle. Before this I once bought a blouse, but I ended up returning it when I notice some discoloration, and some hosiery. The last thing I bought there was a lovely bracelet. It is pink and gold.

As I mentioned an item of jewelry this is a good time to say somethings about my Amazon shopping. The majority of my wardrobe has come from there. I had picked out and then received as gifts from Bette two necklaces and one bracelet. I bought a bracelet similar to the when she gave me. They were both rose gold with engravings on them. The one that I bought has on the outside “She Believed That She Could, So She Did,” which was purchase to motivated me during the trying times of voice feminization training (received free from a local university with a graduate student with the professor, who headed the Speech Lab, supervising). The one Bette gave me was engraved on the inside, and said “You Are My Sunshine.” But, I have bought more since: I have a total of eight bracelets, seven necklaces, six earrings (I had to get my ears pierce twice), and three rings. Just like a woman. Well, not all women of course.

A good chunk of my wardrobe comes from Aldi when they have special buys. I have gotten a jacket, skirts, tops, shoes, socks, bras, and panties. But, when I started getting the Covid-19 stimulus money my wardrobe ballooned. Some of the stuff was from Aldi, but the majority as mentioned in the previous paragraph were bought at Amazon. Covid-19 does put a damper on things as you can’t try anything on, except shoes, which I have bought in store. Two I bought at DSW, and I got another one from The Shoe Depot.

I now have many skirts (almost beyond count), some dresses and bedwear. I also have many shoes. Funny I don’t have enough socks (lol). Of course, I have undergarments: bras, panties, and hosiery. I have enough stuff to fill a whole bedroom closet and two dresser drawers. Did I mention jewelry? And, plenty of makeup? Gone clothes and accessories crazy I would hazard to guess.

And, most recently I purchased a couple of aprons as a set. They are both have floral patterns and some pink among the multiple colors making up the patterns. Bette bought me my first apron for my birthday a month before the start of my transitioning. I figure since I spend a good deal of time in the kitchen, why not include aprons as part of my wardrobe. I can’t imagine that these last two will be the last ones I buy or receive as a gift.

How did this transformation come about. One thing is that women’s clothing has way more options to wear than men’s, so dressing is more fun; it actually brings joy—a good deal of joy. This never happened when dressing in men’s clothing. Another phenomenon can appear. I am talking about gender euphoria, which comes to me at times. This is like a wholesome contentment and joy with being a woman. At least that is the best way I can think of saying what it is like. Personally, I just feel more comfortable in women’s clothing, which feels like the right clothing to wear for my gender expression. Or, that’s the way I see it.

Another thing that might drive this clothes thing is I had finally freed my feminine self, and I exploded like a geyser. Freeing my feminine self is probably the most important factor, and also a very likely one. I say this because there were other feminine traits waiting in the wings that bubbled up unconsciously. The main one being using feminine mannerisms. The way I sit, the way I stand, and the way I walk. As talk rhymes with walk, let say that when I started feminization voice training, which is more than just a higher pitch range, I found that the way I used language also matched up closer to the feminine usage. Also the immediate adoption of paying attention to my intuitions, which I feel women are more apt to do than men.

Finally, life just feels better in a skirt. Skirts are my most often worn item of clothing, except panties. You can find me in a skirt on average 80% of the time, except for sleep wear. It doesn’t matter whether I am going out or staying at home. It is hard to say why this is. I can only guess that it is gender affirming, but also feels the most natural. I can even feel a bit out of kilter when I am not in a skirt.

As you can see I have been through quite a transformation when it comes to the clothes I wear, and the various activities I do surrounding them, like clothes shopping and fussing over what to wear. I would add that I also do some ironing, which I had not done at all or rarely at the least. I feel this transformation has come about because it feels better and brings joy; it fits into other womanly traits or behaviors I find myself having or doing, which has been freed up after recognizing myself as a woman.

And finally—life feels better in a skirt—yay!

† I was in the second cohort. There should be a third cohort in the future, but as of yet it has not started. If you are interested you may check out there website – (this is from the time of the 2nd cohort, now over).

‡ It was really rather cute. I was just starting out for my walk, and the little girl coming home with her mother (both of whom I was friendly with) pointed at my shorts and declared: “they are women shorts.” I replied, “yes they are,” and went on my way. I would eventually come out to both.

^ When I mention what is feminine and what is masculine, I am talking in generalities and about the statistical. And, I fully admit that I am socially influenced as to which is which.

3 thoughts on “My Clothing Journey

  1. I love skirts, but as I spend so much time in the car jeans are just far more practical to be able to switch presentations. It sounds like you have had fun exploring your sense of fashion freedom though!

    Liked by 1 person

    1. Hi DeeDee, so nice to receive your comment. Practicalities do win out, like me wearing leggings in cold weather. I feel your day is coming where jeans will not be so much a practicality, but a choice. Even now with so much to choose from I bought a new pair of PJs yesterday. Do you think I need to write a post on clothes addiction (lol).

      All the best, Stephie

      Liked by 1 person

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