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How a Musician Recovering After Gender Affirmation Surgery Shops

Simon, 30, spent four years saving to afford their top surgery.

An illustration of a piggy bank with a coin going in

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Welcome to Racked’s How Do You Shop? series, in which we ask a variety of people some deeply personal questions about how they earn, save, and especially spend their money. If you know or are someone with an interesting relationship to $$$, email

Simon, 30, spent about four years saving for top surgery, doing odd jobs around their Florida town. Now that they’re recovering post-op, all they can think about is how great their shortalls will feel this summer without a shirt.

What is your job?

I bartend at a brewery for money. I’m also an audio engineer for myself and for others, and I work as a stagehand for large arena events and touring shows. And lastly, a copy editor. Each one brings in just a little extra trickle each month.

I spend maybe 30 or more hours a week doing money jobs, and then I spend 20+ hours a week doing music, at least. My band isn’t always a paying job — I make little bits here and there.

What’s your annual salary?

I would estimate around $30,000 this year, including an artist grant, but it varies every year.

How much do you spend on rent or housing?

I have very cheap rent — $450. My total monthly expenses are around $1,400 for my basic costs — car payments and insurance, health insurance, all these things.

You underwent gender affirmation surgery recently. Tell me about those associated medical bills.

I identify as trans genderqueer. For me, my chest has always been a place of dysphoria. One of my top priorities over the past five years was to save for the surgery. The surgery is incredibly expensive. My insurance doesn’t cover it and doesn’t work with the surgeon that I went to.

It was all out of pocket, and it was $6,500 for the surgeon’s fee, about $2,000 for the hospital fees, and then I’m out of work for two months, because it’s a really invasive surgery. Probably around $10,000 to $11,000 is the total cost.

It’s more invasive than a reduction. There are a couple of different surgical options, but I chose the double incision method, where essentially they cut under the pec of each side and remove all the breast and fatty tissue. I also had a nipple graft, so they totally moved and changed the size of my nipple. It’s more of a re-sculpturing, I guess. It’s a lot longer healing time.

Because all my jobs are physical, I was recommended to take eight weeks off before going back to lifting my arms and carrying things.

Tell me about your fundraising efforts.

So I was saving for about four and a half years on my own and reached a pretty decent amount that I felt good about, but then as it was drawing closer, I think the reality hit that, “Oh my God. I still don’t have the hospital fees, and I’m about to not work for two months, and I’ve just been really optimistic,” you know?

I shared that with my brother, and he made a GoFundMe for me, which is super incredible and sweet and tender, and I would have never expected or guessed that he would do that. So that’s been going pretty well. I also had a fundraiser on my own.

I’ve always known that I was in a really strong community, but I don’t think it was until this month that I really realized how powerful that support can be. When you really feel it, and you really need it, and people show up in all different ways. There’s always a part of me that’s thinking about deserve-ability.

I think everyone maybe has some version of this, like, “Am I deserving of this kind of affection? What is everyone’s capacity for me?” I’m privileged to have not had to do this alone. It is really humbling to have so much support during this time.

Let’s talk about how your style started changing, and how you’re going to move forward with dressing after your surgery.

There were steps in my social transition. Each step was just closer and closer to personal liberation. The first step was when I cut my hair. It just felt like all those years of baggage legitimately fell away. That was an incredible start, and after that, I slowly started transitioning my wardrobe. Of course, this is not an overnight thing. I always had kind of a butch style, but it was tight and I wanted to wear looser garments. I had been shopping in the masculine area in women’s sections from years of that being ingrained in me as acceptable instead of just shopping in the men’s section. In some ways, I had to relearn my body.

I remember that first moment when I had that feeling of, “I can wear anything in my closet and feel really good and feel really sexy.” I mean, there’s always some dysphoria present, but not from the way that this hugs or touches me or makes me feel strange when I go out in public. This is why clothes and presentation can provide such powerful affirmation.

I’ve always worn button-up shirts and jeans that are unisex, pretty much. All genders wear skinny jeans. All genders wear tapered cut, it’s all the same. But I think when I switched my underwear over, that was really life-changing. Even though that’s something between me and my intimate partners, that moment was one of the most powerful.

I got this really cute pair of short overalls from Topman. I love them because I just look so fucking queer, like this cute little androgynous train conductor. I’ve been daydreaming of wearing them without an undershirt.

I like shopping online, but I do also shop in-person. I think as a trans and genderqueer person, you somewhat get used to people looking at you strangely. You have to learn how to reclaim and take up space. That is especially true when you’re in department stores. I’m a bargain shopper; I’m a sucker for T.J. Maxx and Marshalls.

We talked a little bit about transitioning into different underwear. How did that work?

Oh, I get all my underwear from T.J. Maxx because they have the men’s packs of those really soft silky Calvins, and they’re super cheap. I wear men’s boxer briefs exclusively. I would say that was actually probably one of the last things that I updated, and I didn’t realize how significant it would be. That was probably three years ago that I started wearing boxer briefs. I was like, “Why did I wait so long?”

I would also say binding was really helpful. I started binding five years ago, and I’ve always had a fairly small chest, but having a flatter chest was just incredibly helpful for my self-esteem, having shirts fit properly and being perceived the way that I was presenting, feeling seen. Undergarments are really powerful.

What would you say is the most surprising thing that you’ve learned from shopping for affirmation pieces, or stumbling upon them?

Men’s and women’s clothing are made very differently in the way that they’re constructed, their quality and durability. Their costs aren’t very different, but women’s clothing is less durable. I think women’s clothing is purposefully made to be bought and disposed of every month or two months. Men’s clothing, typically, is much sturdier and is obviously meant to last a lot longer. It was surprising, but also not, because of sexism, the fashion industry, and the way that capitalism works.

Also, women are supposed to impress and be colorful all the time and wear fresh seasonal things, and you have to have a new dress for every fancy occasion, you know?

Also, the differences in men’s underwear: Some make a lot of room for packages and have ways to accentuate the package. Maybe that’s why I like Calvin Klein so much, because when I look down, it doesn’t feel like there’s something missing. Whereas a lot of other brands make a huge-ass pocket, like a floppy kangaroo pouch. It’s not like the underwear that I’m wearing has anything missing, it’s just not gratuitously over-accentuating male anatomy.