Right now, I'm wearing my only pair of pants. Ann Taylor yoga pants, stretchy and flowy. I have other pants, but I almost never wear them - my jeans are either full of holes or don't fit, and the other comfortable pants I have are for office wear only (should I ever return).
When I was in high school, I wore the 3 pairs of the same jeans - Gap, size 12, stretch boot cut. They lasted me into college, where they were my daily uniform in conjunction with an ill-fitting t-shirt, Birkenstocks, and a Red Sox hat. The two skirts I owned were strictly for laundry day; friends who saw me in them literally pointed and laughed.
Shortly after I began dating, something changed. I still wore jeans fairly regularly, but I began to buy a skirt here, or a dress there, and wear them once in a while. The size large t-shirts were replaced by size medium tank tops.
Today, I’m making a quilt of my t-shirts and wear skirts or dresses 6.5 days out of the week. But I’m not capitulating to the patriarchy’s need for me to dress up my body and put it on display. I’m not making my legs and ass something to be visually consumed. If people want to look, that's their business, and it's not going to stop me - but they'd better not make it my problem
The shift may have been sparked by a desire to be seen sexually, and that’s probably problematic. But I needed to make a break from my sexless self. In high school, I was mistrustful of men after social abuse in junior high, and I didn’t want them to see me sexually. I had crushes, but I didn’t want dates. Pants put me apart and away from the discourse of dating, and skirts signaled to me and others where I was in life. My gender expression moved away from masculine and towards feminine.
Pants just plain don’t feel comfortable. If jeans fit right when I put them on at 7 am, they’ll be baggy by noon, and I have to wait longer for tight jeans to loosen up. I’m very very tall, and it’s hard to find pants that don’t look Jacksonesque after one wash. If I do find jeans that fit right, they won’t when I gain or lose five pounds – as I do every couple of weeks.
Skirts allow for those fluctuations. An a-line skirt – I don’t do pencil - doesn’t constrict any part of my body. If I gain 10 pounds, I can move the skirt up to my waist with little change, or down to my hips. It allows for movement and freedom. Cis privilege allows and applauds this choice where it disallows it for other women, and it's a feminist choice for me.
There are style concessions I’ve made towards expressing my femininity that don’t really have to do with feminism – makeup, which I wear occasionally, contacts, shaved legs. And some that are enabled but not so motivated by feminism – I almost never wear bras today (thanks B cups) because they just don’t fit and I don’t care. But skirts have been the most liberating style change I’ve made in the transformation of my looks.