I have been struggling with a lot of internalized shame associated with expressing myself more femininely, over the course of my whole life. Sometimes I’m not aware of just how bad it is, just how much negativity I have, until I actually try do something that crosses a gender boundary.

An example would be, when I first painted my nails about a month ago (actually @vanloopy did it for me the first time), I loved how they looked, and I really wanted to do it, but the next morning when I woke up I had this brief moment of mini panic, when I rolled over and looked at my hand. I’m like, ahhh…my nails are painted. Ahh, my hand looks so feminine. And it’s like, I painted them because I wanted to look more feminine. But I had these negative thoughts popping into my head like: “What are people going to think? Are people going to react negatively to me? People are going to think it looks unprofessional. People won’t take me seriously. People will think I’m creepy or that there’s something wrong with me. Is my job going to be jeaporadized? Is it going to be distracting to the clients I work with in my job?” etc.

And like, I had the same thing more recently, when I went, again, with @vanloopy into the women’s section…something I’m often embarrassed or afraid to do. Like initially I used to feel a lot of shame and embarrassment just walking into the women’s section and looking at the clothes. I actually loved shopping though, I found a bunch of stuff I liked, two cardigans, a pair of shoes, a pair of skinny jeans, and a T-shirt. The stuff seemed to fit me well and fit my sense of style. After trying on a couple things, like facing the shame head-on, it vanished. I was like, whoa, I like how I look in this. And I look more feminine, and I like that. I started to feel more comfy, and I approached two of the employees and I was like: “Hey, I want to wear some women’s jeans, and I have no idea where to start with women’s sizes, do you have any advice?” and they tried to help. I ended up buying five articles of clothing.

But then going to wear it, and then actually wearing it, I sort of had these other moments of fear that I needed to confront. I was initially quite afraid of wearing the items out and about. And then I was like, whoa I am wearing women’s jeans…and it was kinda striking because I could see all around me, most of the women wearing jeans as I went through my day, were wearing ones cut / fitting very similarly to the ones I was wearing, and none of the men were. It’s like, I know I’m not a man, but I also know that people still perceive me as a man, so I still deal with this fear.

Where does this negativity come from?

I’m not 100% sure but I have some good ideas. I think the culture I grew up in was pretty misogynist, sexist, homophobic, and transphobic. I grew up in Lancaster county, Pennsylvania, and even though I went to the city schools, and the city is more liberal and multicultural, I think I absorbed a lot of negativity about male-assigned people expressing more femininely. I was bullied when I expressed myself or acted more feminine around boys, and I also saw boys bullying each other, and I saw people talking about girls in derogatory ways as well, the whole “shaming of femininity” thing that feminists talk about. It seemed especially harsh directed at what I would call “girly” aesthetic or expression (which is what I most want to embrace) and less at the aesthetic or expression of older, more “professional” women. I also think my family has sometimes been negative about certain aspects of me expressing more femininely (even if they’re completely accepting of, or even appreciating of, others).

I think I’m past this though: over this past week, I wore all the articles of clothing I bought, and I was surprised at how many compliments I received. It was like, almost non-stop. People were like, wow, you look amazing in those jeans. Wow, those jeans. That cardigan, I love that color. I love how that cardigan fits. I love how your cardigan is so soft. People gave me compliments when I wore the clothing together, and people gave me compliments when I combined it with other items of men’s-section clothing that I already owned. Wow, that color combination. I got a variety of different types of compliments, including some people who said that my outfit “didn’t really look that feminine” when I told them it was from the women’s section, but also one person, who pays a lot of attention to fashion, and whose fashion sense I really like, came up to me and said something to the effect of: “I really love what you are doing with your outfit, like wearing things that are moving more into the range of feminine expression, and it looks really natural and looks really great on you.”

And I’m just like yes this is what I am going for!

So like…this whole process is really empowering. It feels like I’ve pushed through most of the internalized shame or negativity and suddenly my head is full of ideas of new things I want to explore. I’m like, so excited to go shopping again. I want to go to different thrift stores and different retail stores and see what I can find. I want to try on my friends’ clothing when I have friends with similar builds to me. I am also excited for summer to roll around again too, because I want to also explore various more revealing outfits (a week ago this was just dreaming, now I feel excited to actually explore this).

I’m just like, so pumped. I feel like I’ve wanted to do this for years.