Well yesterday I made the first step of shedding my old look.
Since the weight loss started in March I have dropped from 300+ lbs down to 217 today in September. I feel good, I think I look a lot better (but I do feel I am not done), and because of this I have a LOT of clothing that I can’t wear.
Most of the clothing is my boy clothing of course, especially my work clothes. I have a ton of clothing that is just hanging out in boxes and bags because it won’t fit me. Yesterday we decided to get rid of the clothing, and not to keep it any longer “just in case”.
We will be giving my boy clothing to my younger brother. He doesn’t have a lot of good clothes anyways and I like being able to help him with what I do have. Combined I am giving away
14 T-Shirts
- 1 brand new suit (bought in march)
- 5 belts that are way too long and can’t be cut down.
- 5 long shorts
- 2 gym shorts
- 7 polo shirts
- 4 casual office pants
- 3 jeans
- 8 dress shirts
- 4 dress pants
- 1 pair of fatigues
- 1 sports jacke

This leaves me with a few bits of boy work clothing that are much smaller size (from waist size 46+ to now a 36, same with the shirts in reduction.
The surprising part is now I have to get rid of all my initial girl clothing as well, and that is the clothing that made me feel a tinge of worry and maybe regret. None of the boy clothing did that.
Don’t get me wrong, it is great I went down from that size, but it is still a little sad. Also, I will probably have to shop in plus size most of the time anyways no matter how skinny I get, since I am 6’2″+ tall.
So next month when I go up and see my brother I get to give him a new wardrobe. Both the hubby and I figure even if I gained weight back, I won’t be wearing those types of clothes by the time it happens anyway.

I am still working on my new wardrobe. The hubby is busily buying things for me as he finds them, and we are both surprised at the sizing getting smaller as we go. He says it is the first time in our 26+ year relationship (26 years married on Halloween, then a couple years before that) that I seem to enjoy getting clothes. I think he is right.
Overall the experience of shifting out clothes is distorted by my body changing shape. I have some pictures of me just in underwear from March of 2018 (what I looked like under the suit) vs now in September. However I don’t think I am ready to see that up here yet, it really makes me dysphoric.
The funny part about this is I couldn’t name why I hated myself so much before I decided to transition, but I truly did, and I still struggle a little now. Although it is getting less, and I am starting to like what I look like better. That is probably a whole entry by itself, but not today.
So there it is, I am making my first full step in shedding my old self, by packing up forever my old clothing. It is scary, but also pretty exciting.
The first few rounds of clothing from the right side of the store all contain magic.
And most of mine from that time are no longer in my wardrobe. Some of that is body change, but most of it is evolution of style. At first, I was looking for thing that looked good on me at all, and was giddy when I found something. Now that I have far more experience both wearing and shopping, I know what I look great in. Good-at-all isn’t the standard any more.
Still didn’t make losing those first pieces any less hard.
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I especially feel bad because some of them I wasn’t able to wear before giving them away. I agree though, I am learning with the clothes I have now that I have to set up looks, organize it a lot more than when I still presented as male.
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