A Fashion Guest

A style interview with my gender-queer best friend

I’m trying to publish my newsletter on Sunday morning instead of Monday so it doesn’t interfere with my workday but I’m a little bit late today.

How was the holiday for everyone? Mine was mellow. I had friends visiting from Arizona and Seattle so I spent a lot of time at home cooking and relaxing. We had a quiet dinner and made brisket instead of turkey because we’re old and we can do what we want.

I did buy a few items from the Black Friday sales. I didn’t get everything on my list from last week and not wanting to pull the trigger on some of the things helped me cross them off my wishlist.

Sometimes when I’m getting dressed I find I’m wishing I had an item I don’t own and I write it down and then try to find a version I like online and that’s how my wishlist gets created. Usually these items stay on my wishlist for a long time. And then there are the random things that I see online or in a shop or someone else wearing that I fall in love with and these things also go on the list. Usually they don’t stand the test of time but I bet this outfit will:

Here’s an outfit I saw Allison Bornstein wearing recently on Instagram that I’m obsessed with and putting on my wishlist. The top! The belt! The all black but with beautiful texture and details. I love everything she’s wearing in this reel.

And then there are the items that I feel like I “should” buy and never really want to, like a new bra or underwear. (These are my current favorite underwear from Negative.) Or it could be something I own and think I could use another one. A good example of this is the Jenni Kayne Flynn cashmere sweater I mentioned in my last newsletter. I have one and I wear it a lot so I told myself I should get it in another color. But I don’t actually want or need to own two of the same sweater, and when it went on sale I realized I’d rather get a different sweater than a repeat of one I already have, so I didn’t get it and crossed it off my list.

Next week I’ll show you all the things I DID end up buying from the Black Friday sales. I think I did well, kept my head on straight, and only bought things I’ve been wanting for a long time. As in, I didn’t buy this dress even though I wanted it so badly and had absolutely nowhere to wear it.

Shopping at the Eileen Fisher store on Black Friday. I bought a t-shirt for $34

I just finished reading Reconstructing Amelia and I thought it was good but not great. However sometimes I like a book that doesn’t totally grip me and take over my life, but it’s interesting enough to read for half an hour before I go to sleep. That’s what this book was. Next my friend and I are going to read City of Night Birds which got pretty bad reviews but we’re both obsessed with ballet so we’re committed.

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Now for the main event. I’ve been wanting to feature other people in my newsletter for a while but I’m not always that organized. However, I live with my best friend and they’re into clothes so every time they put on an outfit I liked I’d snap a picture in front of my neighbor’s cool door and I’ve been saving them up. This felt like a good week to feature them as my houseguests were staying in my room where all my clothes are, so I basically wore the same pair of sweatpants every day for the last week. (These from FreeCity)

So here is Andie, my stylish housemate and civil liberties lawyer:

It’s going to be a little harder to link all these outfits but I’ll do my best. Eileen Fisher silk cargo pants. The top is also Eileen Fisher. Sutro boots.

How would you describe your style?

I like clothes from both genders; I try to mix them in a way that works for my body. I don’t mind including gendered clothing because I found the androgynous aesthetic boring after awhile. For example I’ll mix masculine hats and shoes with feminine outfits or vice versa.

I did go a little overboard with mini-skirts when I first came out. Once I started developing breasts I wanted to show them off. But the pendulum swings back naturally and I went through an androgynous phase to see if it would satisfy me to dress completely down the middle of the gender divide. But as I mentioned that got kind of dull.

Now I’ve reached a more playful time and I try to tap into whatever gender feels right in the moment and dress accordingly. This is fine but sometimes I end up changing my clothes three times a day. I’m only partially out at work so that requires some negotiation. I’ve gone to the office in a dress and a skirt but I haven’t gone to court dressed that way. And I’m not out with clients who aren’t trans because the legal system is very patriarchal, although I do belong to the National Trans Bar Association.

Old sweater from Madewell. Nike Dunks. Trucker hat is from Naramata, Canada where we have a summer place.

What are some of your challenges in getting dressed as a gender-queer person?

It’s a challenge having an AMAB (Assigned Male At Birth) body and trying to fit into clothes designed for CIS-gendered women, but you start getting used to it. If I’m wearing women’s clothes I have to compensate for the lack of a waist, my broad shoulders, and long torso. I deliberately don’t wear things that emphasize those aspects of my body. I try to choose things that give shape like a-line skirts and tops that break up the length of my upper body. It’s hard to find feminine hats that work for me and a lot of women’s footwear doesn’t work because at 6’2” I’m not going to totter around in heels.

Matteau silk shirt. Here's one in blue. Shorts are from Ad Hoc in Penticton found on the sale rack last summer. Nike Dunks. I think this is where the hat is from, or should I say chapeau.

What are your favorite places to shop?

I like Eileen Fisher because it accommodates larger torsos without somehow being too tent-like. Negative underwear works well on trans bodies. Emerson Fry is good but it can be tough on sizing. Sometimes I get clothes made to fit like the linen dress I wore for the wedding (below). You can give the company your measurements and they’ll make you a custom item.

Andie is wearing a beautiful woven cotton top but the tag just has a logo on it which I can’t place. And I’m the one who suggested it, but it was a few years ago… Pants are from Cut Loose. Shoes are from Pikolinos. Same hat as above.

What was it like to start wearing women’s clothes in public?

I transitioned at the age of 56 and I’m typical of a trans person in that I was very hesitant and even terrified to go out in public in a dress for the first time. I felt like I had vertigo when I walked out in women’s clothes but it turned out no one was paying attention. It probably helped that I was in Noe Valley in San Francisco.

Negative Underwear Club Pullover. Tan sweatshirt cardigan is from a local brand called Kosa. Pants are from A New Day. I found some of their clothes at Target. Same shoes as above.

What’s an iconic look that stands out in your memory?

Part of the challenge of being trans is that you don’t have a lot of icons. Yes, there are trans models but they’re young and slim so it’s easy for them to wear what they want. I’ve felt some sadness about the fact that it took me so long to learn who I was and I didn’t get to play with trans style when I was younger, but I’m happy with the person I’ve become today.

Emerson Fry Layering Jacket. Dress is older from Sanctuary. Same shoes as above. Hat is from Travaux En Cours. Sparkly tights from Amazon.

Is there a particular outfit that you recall that made you feel most like yourself?

That’s the thing about being gender queer: you don’t just have one self to feel like. In a way I felt most like myself in a size 18 Tinkerbell outfit (sorry there’s no picture of that one). I guess I can’t really speak for anyone else, but my guess is we all have lots of selves who want to be expressed at different times and in different contexts. Connecting with different internal genders has taught me to be more creative and free in expressing who I feel like in the moment.

Dress from Shop Xiaolizi. The vintage Miu Miu bag belongs to yours truly.

Andie runs a trans meditation group and if you want to find out more information you can check out this flyer:

That’s all for this week. I hope you enjoyed my guest post. I hope to do more in the future as I have a lot of stylish friends xo