Things change, but high waisted skinny jeans are forever

I worked as the executive director of a music industry association. To date, it’s the fanciest job title I’ve ever had, which secretly simply means “writes a lot of emails.” The first time I came to work dressed as myself, I was a hesitant toe dipped in a bottomless pond, I was wearing a black and white horizontal striped shirt I had bought from Frank & Oak five years earlier early on, a skinny high-waisted black Levi’s and a cheap pair of four-inch-heeled combat boots that I bought on eBay at 2 a.m., painted my nails black, and one of my employees later told me “I just thought you had gone goth or something.” Can you imagine becoming a goth in your mid-thirties? I would simply die.

I lived in the Yukon for the first year or so of my transition, and the unofficial slogan there when I was growing up was: where men are men and so are women. I found it difficult to accept myself as a woman and to manage the expectations of masculinity imposed on this femininity in the environment in which I lived. Also, I worked in construction for almost 20 years, and there was a very strong sense of who I was, inside and out.

Needless to say, I really had the idea of ​​cutting all the sleeves off my old t-shirts just low enough that I had to wear a bra underneath. My first phase of trans baby/gay baby/dyke baby. My favorite was a Dinosaur Jr shirt, gray with darker gray detailing, which I trimmed maybe a bit slutty. I would wear this with high waisted skinny Levi’s – forever my favorite – and Blundstones and, if I had a business meeting, a little cardigan to class things up a bit. This outfit often looked bad, but it was nice, and honestly, that’s more important.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging from a hook is a gray sleeveless shirt with an image of a girl smoking a cigarette and the text Dinosaur Jr, sitting below is a pair of black jeans and a pair of dirty brown Blundstone boots

I really liked tank tops for a long time. A gray or red tank top under an open flannel shirt paired with – you guessed it – Levi’s high waisted black skinny jeans and brown Blundstones. I didn’t express anything with this outfit, but I didn’t express anything. It was like being really bad at hide and seek. I thought if I dressed like that, no one would notice that I wasn’t like I used to, but I was also terrified of anyone seeing the real me.

The week before I left the Yukon forever, I wore a shirt with a pattern of a lobster and little sticks of butter over a gray She Shreds tank top with a mesh baseball cap that had Loser written on it. You could say that decisions were made, but it was rather that they happened to me. Perhaps that is what it means to grope towards ecstasy.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging from a hook is a gray sleeveless shirt that says She Shreds under a white short sleeve button up with a pattern of lobsters and butter on it, sitting below is a pair of black jeans and a pair of dirty brown Blundstone boots and a hat that says LOSER on it

When I first landed in Toronto, I was so tired and ready to hide and recover. I wore sweatpants and stayed in my friend’s loft where I – and two suitcases of outfits that I actually hated – hid in a bedroom. I wore the same Sleater-Kinney shirt cut as a tank top for most of the first month and smoked cigarettes on an emergency exit where I made small talk with people in the building confused about My gender. Frankly the same.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging from a hook is a green tank top that says Sleater Kinney on it, with line drawings of houses and mountains below sitting below is a pair of gray sweatpants with a white drawstring

I moved into the guest room of another friend’s house and slowly began to unpack my suitcases and my life. Hanging all your clothes on the wall really puts a lot of things into perspective, and I gradually realized that I hated all those clothes. I realized that I was living in a town where no one knew me, my past or the idea of ​​my future, and I could do whatever I wanted! And what I wanted was the H&M in the mall, the one near the Cinnabon. I bought blouses, one pink and one with a little pattern on it, and basic t-shirts. I allowed myself to wear nice clothes AND I was excited. I always wore Levi’s high waisted black skinny jeans, because some things work.

The first winter I lived in Toronto, I decided to buy Doc Martens. I was a teenager in the 90s, but I didn’t tell anyone I was a girl back then, so I kind of missed that whole scene. But because everything in time and space eventually returns, I could finally be the cool ’90s girl I’ve always dreamed of. No one warned me about the whole “your heels will be shredded unless you rub Vaseline inside the boot”, and I lost a lot of great socks in the process. Doc’s was a good call though, and they unlocked something in me. Maybe I was a 90s cool girl?

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  A pair of black Doc Martens sit on a brown shelf

Niko is my second legal name and third gender or whatever. If I have any advice for trans babies, it’s to REALLY know you like your name before you pay to make it real in the eyes of the state. It’s boring when you’re trying to get a new driver’s license and people think you’re the boring part of every spy movie with a bunch of different names on passports in a shoebox. I found my name when I realized I really liked being a woman, when wearing tank tops under the flannel got boring and I started buying things like a silk blouse from Everlane and a long gray jacket – a style my friend Sarah affectionately calls a long slutty jacket. I was a long female dog. A long female dog named Niko in a Long Bitch jacket.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall is a long gray jacket hanging over a black silk blouse A pair of black jeans sits on a brown shelf

Honestly, a lot of my discovery of my personal style has been through jackets. I really liked the Long Bitch jackets: the gray one that started it all, my favorite brown from Zara that I got on Poshmark for $35, and a vintage gray winter coat with a real fur collar that I loved. bought at the thrift store. When I found the latter, women appeared almost as if out of nowhere to tell me how jealous they were of my find, and I felt seen for the first time. No one here in this Value Village except us girls, who jealously comment on other people’s finds!

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall is a long brown jacket

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall is a long gray jacket with a fur collar

I’ve purged and given away so much from my wardrobe over the years since I’ve been out. I have drawers full of essentials that are dull and boring to me now, that were hard to accept that I needed in years past. I own pretty bras that cost way too much, silk blouses and flowy things. For Christmas one year, my partner and I decided to invite two friends, and for that I bought a sleeveless black dress, cute boots and fun stockings. When I was putting together my outfit, my partner reminded me of when I used to loudly proclaim what an asshole I was. Woman makes me happy, who knew.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall, a black sleeveless dress.  A pair of black boots sit on a brown shelf

When I submitted this essay, I was wearing black leggings with a hole in the knee and a crop top that just said the word Fuck on it. Something I’ve discovered in the last year is how much I like to marry comfort with feeling like I still have some distance from my old life, so wearing leggings and just a bra- bra — or a crop top that says Fuck on it — helps me feel like this is what Niko would want to wear, not what she wore so people wouldn’t ask too many questions.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall is a white droptop that says fuck in lowercase letters.  A pair of black leggings sits on a brown shelf

Some days when I work from home, I dress really well. I wore this dress with sleeves that ended in studs and tights and heels and did my makeup with the firm intention of never leaving the house. Not because I’m scared or hesitant about what’s going on or how people are going to perceive me. Fairer because of deadlines, and coffee is cheaper when I make it myself. I don’t really care what other people think of me – that period of my life is long gone – but it’s nice to remember how terrifying it was to be a trans woman from a 30s trying to figure it all out, feeling like I’m going nowhere, being where I am now and knowing it’s more fun to dress well for myself than perception from someone else.

a brick wall, with a picture of PJ Harvey in the upper right corner and a power that says Long Winter in the left.  Hanging on the wall is a long-sleeved black dress with rhinestone studs at the end of the sleeves.  A pair of black boots with a brown heel stand on a brown shelf


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