Amanda: I've been making my own clothes for the past year and a half or so. And it's been really fantastic because one of the things I learned is that the problem with getting clothes to fit correctly is not a problem with my body. The problem is with the way that clothes are sized in stores.

This is Death, Sex & Money. 

The show from WNYC about the things we think about a lot… 

…and need to talk about more.

I’m Anna Sale.

For Amanda, a listener in Vermont, taking the time to make her own clothes during these last few years has shown her that her body is not the problem. It was the clothes she was buying to wear.

Amanda: I find that I'm actually three different sizes in different places on my body. So I feel like in this way, the time during the pandemic actually gave me a really strong understanding of how to dress my body in a way that's flattering and has given me a lot of confidence.

Pandemic times have given a lot of you more permission to change things up in how you look, like for a listener named Kelcy…

Kelcy: I started to explore with my hair by like shaving the back of my head and then shaving all the way, the entire undercut, and then cutting bangs on my way to a dance competition with my daughter in the car.

We’ve been collecting your stories about personal style for months, and along with these bold victories, we’ve also heard about your fashion frustrations.

Listener 1: I am knee deep in perimenopause. My body is freaking out and basically having a coup against me.

We heard how child-rearing has changed your body, and what you have to wear.

Listener 2: My dressing decisions are exclusively based on how easy it is to take my boob out of an outfit.

…and you told us about the clothes you have no longer fitting your gender identity.

Listener 3: My body and my presentation has changed a lot, but I'm still really struggling to just present more feminine and get to really enjoy and express more of what that gender means to me.

We heard from so many of you who are just exhausted with dealing with the struggle of figuring out what to wear every day.

Listener 4: I just feel like I am tired of not dressing like I wanna dress, I'm tired of not being, um, I'm tired of not being the person I act and feel like. 

Listener 5: The most, like, fashion forward thing that I do during the week is like having on some fun socks. 

Listener 6: And I have struggled with dysmorphia my entire life. Something that feels good one day might feel terrible the next.

Listener 7: I'm currently walking my dog in a pair of bike shorts and a really big t-shirt. And this is my ideal clothing choices. Um, I hate clothes.

So many of you are all about prioritizing comfort and ease above how others perceive you. 

But then, we heard from a few of you about the very opposite – about how using your fashion to be noticed by others can be really joyful, and an important way to build community and find your people.

Like for Stephen Antony Beasley. He’s 42 and has always been a fan of fashion, whether shopping in vintage stores, or more so now, quietly scrolling alone.

Stephen Antony Beasley: Um, Instagram… as we know, sort of shops for you.

Stephen grew up in Louisville, Kentucky, but has lived in New York City for the last 20 years. He’s a musician who currently works in public health.

Stephen: I just have glimpses of like, um, of a still evolving, personal style of like, what I'd like to think is kind of a cosmopolitan Black middle aged man, right. And I, you know, I still get compliments on the street sometimes and it's usually from things that I've purchased over five years ago.

The last few years of Stephen’s life have brought a lot of changes. He got married, bought a house in suburban Queens, and became a father to his 8 year old stepson and 10 month old daughter.

And with all those changes, he told me he feels like he’s lost a part of himself as he struggles to find time to focus on fashion.

Still, when I spoke to Stephen over Zoom, he was wearing a statement piece: this colorful suit jacket embroidered with roses that he wore to the Kentucky Derby. 

Stephen: The suit with the alterations was 179.

Anna: Oh my gosh. Amazing.

Stephen: I don't play. I can't play, I can't play. Yeah, if it's a purchase, it gotta really make sense and it needs to go the distance.

Anna: When you think about like a, a piece that feels like an exciting, maybe a little bit of a fashion risk, um, right now at this stage of your life, in your early forties, as someone also in their early forties, like, does that look different than something you would've picked for yourself 10, 15, 20 years ago?

Stephen: A hundred percent. I mean, I'm, I'm, I'm married. And then, you know, and I have an eight year old son um, and I, I look back fondly–

Anna: Do you like to like lean into like the daddy look? Like I'm a daddy, I'm gonna look like a daddy. Like there's a hotness to that too.

Stephen: Yeah, but you know what, that doesn't get my wife riled up.

Anna: Uh huh.

Stephen: She wants– this is, like when I actually combed my hair and slicked it back into a ponytail and combed my beard today and put on this jacket, I saw her look twice when I walked out the door. Like, I look back with fondness on some of the, like more costumey things I did in my early twenties, like, I don't know what that thing in the early 2000 was with like safety pins and paperclips, like clipping like clothes that were like clipped together. Every, uh, things were ripped to shreds and I mean there was one time where I had like a Spanish conquistador looking hat that I used to wear, like in the mid aughts. Um, but it's not as costumey now, as far as I'll go now, is like maybe like an extreme print. Like I have this ridiculous lime green shirt that has a bunch of bananas on it.

And part of what makes all of these changes so hard for Stephen is that losing the ability to really dress up has made him feel disconnected in a way that crept up on him.

Stephen: Really, when I think about clothing, I think about my entire life and the experiences and the people. Like the first memory of clothing is like Garanimals in the early eighties from my mother. And then my dad took me to TJ Maxx in the middle of a hail storm in Savannah, Georgia. And if you've ever been down there, that was not that safe, but he was sick of me being scared. So he said, this is your time to go school shopping. And we moved through what my proms were and homecomings in high school and the different looks in college. And then, you know, just starting my adult life in New York and forming the communities that sustained my adult life and really affirmed me. And this is where the pandemic really hurts. There was just a community of folks around me and we had created a flow of reciprocal, healthy relationships that made each year have this arc, this beautiful arc of like who I would see and who I would be in community with and the experiences that we had and the shared histories that we were, um, that we were yet creating. And I talked myself into the fact that like the clothing in all of these memories is like the, the, um, the, the set of extras that don't have any lines. 

Anna: Mm. I mean, your description of, of the clothes being the extras in this community, that you had been a part of building, like in, and even those other fashion memories you described, it's like each memory you described was about a relationship with someone else. And so it makes sense to me that, um, this time of isolation was a little unmooring of like, who am I dressing for?

Stephen: I'm actually never dressing for anyone because everybody who really, really, really, really, really cares about me up to and including my wife is not really with what I wear at all.

Anna: Well, you're not dressing for them–

Stephen: It's so funny

Anna: –you're dressing for the compliments from strangers. It's okay!

Stephen: I guess that’s what it's always been about because yo, like very rarely. I mean, I'm talking about from my mother, my dad, my grandmother, all of the best, best friends I've ever had. It's usually not the people closest to me who like my clothes the most. And if one of those really close people give compliments, I'm like, oh, I really must be doing something.

Coming up… how one artist uses fashion as an extension of his creative process and why even the smallest details speak really loudly.

Bill Walker: Well, it's like a daily collage. It's a daily practice. I mean, I, I think that it's, there's creativity so deeply rooted in fashion, being fashionable, to me. And playing with fashion is a huge and important part of my identity.

We heard from many of you asking for advice about how to approach your new style. Many of you are feeling the need to mix things up fashion wise, but don't know where to start. And that's something we've been asking ourselves here on the team. The original idea for this episode actually came from one of our producers, Afi Yellow-Duke. She wanted to reconsider her own style as she approaches thirty.

Anna: Hi, Afi.

Afi Yellow-Duke: Hi, Anna.

Anna: So this has been a project since the spring, and you do not have an unlimited budget. You also do not have a celebrity stylist. Who have you found are your style inspirations when you've sort of been looking for something that might nudge you out of your comfort zone, or out of your patterns that are feeling a little bit tired? Uh, where are you finding that inspiration?

Afi: I mean, definitely like many people, I see things on Instagram that are cool. Um, there's one person on Instagram. Their name is Lydia Okello. Their handle is @styleisstyle. I find the way they dress themselves really cool and interesting. They’re really like unafraid of color in a way that I find very aspirational. I also really like, um, there's this account called, it's an account– it's also, um, they put on a fashion show here in New York every year called dapperQ. I find menswear and like suiting really interesting. And they just tend to have really cool ideas of like queer independent labels that are making cool more, I guess like masculine cut clothing, which I think is very cool.

Anna: That's cool. And for any listener out there, who's just thinking like, how do I get out of my ruts? Any kind of like broad advice you have for somebody who's wanting to do the same thing you're doing?

Afi: I think just start with one thing, like one, like, item of clothing, rather than being like the whole outfit has to be different. For me. I feel like I've started with like, oh, what's like a top I like… clearly it's in here, but maybe I don't wear it very much.

Anna: Because you are, you're currently recording in your closet to be clear.

Afi: Yes, I am in my closet right now. So I'm looking at some of the tops that I haven't worn in a while and I'm like, hmm, I think I need to find a use for that.

Anna: So that's another very practical piece of advice. Just sit in your closet if you're working. You know, spend part of your work day in your closet and you might find some inspiration.

Afi: Yeah, take your meetings from your closet! See what happens.

Anna: Thank you, Afi. And if you have any fashion advice out there that you'd like to share, we would love to hear from you. You can email us at deathsexmoney@wnyc.org, and we will share more of your stories and tips in our newsletter. You can subscribe at deathsexmoney.org/newsletter.

This is Death, Sex & Money from WNYC. I’m Anna Sale.

As we put together this episode, we also heard from Bill Walker, a queer, trans artist living in Milwaukee, Wisconsin. When he sent in an email explaining the change in his personal style, he included photos, and we were struck by the specificity and boldness of his fashion. Every look is a well put together outfit.

And that’s intentional. He told me each of his looks is specific to where he is and what he’s doing.

Bill Walker: I tabled at an event, couple months ago. And I was selling a lot of my art, which is very softcore, homoerotic-based stuff. And so I really wanted to play up that kind of overall, the overall optics. I still had platinum blonde hair So I just greased it back. And I had, um, I had some little like John Lennon sunglasses that I had on, the croakies– the little like, uh, the holders that you can hang your sunglasses on. I had um, a little black bandana tied around my, my neck. I had white denim jeans, tight white denim, denim jeans. I had white, uh, Vans sneakers on, and then I had this white shirt that said 'Give me peace, love, and a hard cock.' And I just tucked it in, had my nice little, you know, like creamy, uh, leather belt on. And I just sat back and I was like, this is it, I've arrived. This is me. And it was not the right environment for my art. It was not the right environment for my outfit. But, what happened was that I had so many queers coming in and saying, this is the best booth, and just like telling me their stories and talking about what it's like to be queer in Milwaukee and just having a wonderful time. So it wasn't necessarily a, a space built for me, but I created a space for me and other people. I mean, I'm dressing an entirely different body, and I would say I knew how to dress myself before, whether it's looking for clothing sizes or it's looking for, um, shapes and what worked for me. Before it was play, and now it feels more like exploration.

When I spoke to Bill over Zoom, his blonde hair was in a shaggy short cut, he sported a mustache, he had a handkerchief tied around his neck, and was wearing a white muscle tee with olive green shorts.

Bill: Right now I would describe my personal style as sort of, uh, buttoned up western.

Anna: Oh, I like that!

Bill: And I say that because I'm literally buttoning up my shirt all the way to the top button. Um, I'm very much like a bolo tie wearer, um, I think of my origin story as a combination of all of the summer camp horror movies of the eighties and the county fairs that I loved a lot when I was a kid. 

Anna: Where were the county fairs as a kid that you went to?

Bill: I grew up in Monterey County in California. It was a retirement community that was butted up against a lot of farming and ranching. So we had all of the literal Rhinestone Cowboys coming in, people who had, you know, worked on farms, but they're putting on their best. And that was the first time I kind of saw gender bending. So it really stuck with me. And I carried that with me my whole life.

Anna: Oh, oh, gender bending at the Monterey County Fair. I like that.

Bill: I mean, I think that western wear really calls to people. It's like you still get to dress up. You still get to have the fine clothes. You still get to have the pearl buttons. You get to look beautiful, but it's like, you get to look handsome, right? So it's still about preening, it's still about showmanship. It's still about putting together and executing a beautiful look, and allowing yourself to really care. 

So, Bill has long had a specific fashion ideal for himself, but he couldn't execute it the way he wanted to until he had top surgery in November 2020, about a year and a half after he came out as trans. He could finally channel those cowboy looks from the county fair, starting with one particular item of clothing.

Bill: The most exciting thing for me was being able to put on a, a plain white t-shirt. Um, that was so wonderful to me because it, it, it's this weird classic look for masculinity, I think is just like the plain white tee tucked into some jeans, you know? And, and that to me was it felt kind of like freedom.

Anna: Mm. When did that happen? About how long after the surgery?

Bill: I would say that happened maybe… three or four weeks after I got surgery.

Anna: Were you by yourself when that happened?

Bill: Yes.

Anna: Were you like in a bedroom, in front of a mirror? Like, what was it like when you, when you got to put that on for the first time?

Bill: Well I wish that someone had been able to see it because I still had such a, a limited range of motion. So it was very much me putting it on the side of the bed, popping my head through, wriggling. I, I still had T-Rex arms, so I still had this very limited range. I couldn't, I couldn't raise my arms above my, uh, a little bit above my waist. So I wriggled in, and I, you know, trying to pull it with my teeth and, and have these little T-Rex hands. Um, and then, yeah, I set up my phone and I took a picture of me not only wearing this shirt, but also with my arms as high as I could possibly raise them, which was not that, um, not that high, but the look on my face was really, I mean, I, I, I look at that picture when I'm really bummed or things are really hard and I don't know, it feels really special.

Anna: What do you see when you see that look on your face? What is it?

Bill: Well, it's recognizing myself for the first time. I, I mean, genuinely before I got on hormones and before I got top surgery, I would literally look in the mirror and not recognize the person I saw. It was really, it was really upsetting. And to reach this point in my transition where I was able to see myself be happy and to see myself recognize the person I was looking at, the photograph I was looking at, was something I never thought I would ever experience. Before there was a lot of fanfare to my, uh, my fashion. It felt like it was almost either distracting or making up for what I felt like I lacked. And so to be able to just wear these simple clothes was such a goal for me.

Anna: Oh, that's interesting. When you think about clothing that you used to wear, that was, that was part of a distraction, like what, what were some things that you would wear that you think of that way?

Bill: Oh, I had hair, every color of the rainbow. I had, um, really big eyeglasses, kind of fashion eyeglasses that I would wear. I would have my hair bright green or bright pink. I would wear, um, like high waisted, like vintage trousers. So it was just as mu– as maximalism as I could get.

Anna: These days, how much time do you think you spend thinking about and putting together outfits?

Bill: I think about what I wear a lot. It takes up space in my brain that doesn't always feel good. And I think that a lot of my fashion choices are sort of mitigating potential uncomfortable interactions when I go out. And what I mean by that is what am I gonna wear that's gonna get me properly gendered? What am I going to wear that shows people that I'm queer? And what am I going to wear that keeps me safe from harassment? And I really hate that my fashion has sort of taken this turn. And so that's what I mean by exploration, right? It's like how to make myself feel good in my own skin and wearing my clothes, but also feel safe in the community. And I don't think that's much different than how I thought before I came out. But I think I knew the rules better before, and I don't know what the rules are like anymore. And I think there's an element of fear there that's, that's hard for me. 

Anna: And it feels like those objectives, um, maybe sometimes very much cross purposes. How do I signal that I'm queer? How do I find clothes that feel good on my body and how do I not attract, uh, hostile attention?

Bill: Right.

Anna: Um, is there an instance where you feel like you got that mix wrong?

Bill: Well, it's, it's funny, like the way you're wording it is right. But it's also wrong, right? Because it's like, I guess I got it wrong, but it's like, you're playing by rules that inherently are there to hurt you. So I don't know. It's like, I, I mean, I wonder if maybe the way that I would put it differently is like, when was, when did I, when did I put together an outfit that people responded to in a way that I didn't like. Does that make sense?

Anna: Yeah. And do you think of the lesson from that instance as, um, I wore the wrong thing or I was in the wrong place, surrounded by the wrong people?

Bill: I think, I think the latter. Like when I've, you know, quote unquote got, gotten it wrong, it's less of a, oh, I thought this would work and it didn't work. And it's more like I'm tired of playing by these rules. What would it look like for me to just do what I want?

Anna: Are you okay describing, like what, what didn't feel good about that interaction that you're thinking about, what happened?

Bill: Well, I'm thinking about a couple different things. The first instance that comes to mind is walking into any doctor's office, walking into the DMV, walking into any institution that has resources that I need, because there's a level of safety of getting served at the very foundation of what you're looking for. And so it's trying to go in and just present so that people don't question. And the other instance I would say is being in, being in environments where it's only men around, because I don't know what that's like. I don't know what’s a community based, uh, conversation or what topics are okay or not okay. I don't know when playfulness turns into flirtation, it's, there's different rules and I don't know how to play with them. And I've had to go to a mechanic to get my truck worked on and I wasn't thinking about it. And I'm dressed sort of like this, where it's like hot pants and a crop top, and I'm rolling up in my truck and I'm thinking, oh, I didn't do this right. I mean, it feels, it feels very gendered. It feels very scary and it's like a, a, a different side of the same coin, right? I mean, before I came out, before I transitioned, it's like, I can get away with flirting with the mechanics. I can get away with making some jokes. I can get away with not knowing literally anything about how my truck works and I don't have to really worry about how I'm dressed. And then when I'm there as me, as a man, as a trans man, like I don't get to flirt with them to get that extra, that extra 10% off my oil change. Like it's just, it's, it's terrifying. And I, and I really do feel like those are some instances that I think of, of where I've felt concerned for myself when I've allowed myself to stop playing the butch game and just be me, and wear what I wanna wear and then realize it doesn't particularly serve me.

Bill has lived in Milwaukee for less than a year, so he’s also adjusting to life in a new city and trying to make new friends.

He’s been sober for over a decade and doesn’t go to gay bars, so meeting other queer and trans people has meant being open to finding community in unexpected places.

Bill: It's sort of like cruising for friends.

Anna: Mm-hmm! Yeah. Where do you cruise?

Bill: You know, I like hanging out in the allergy section of my CVS, you know. I know there's, I know there's other people that like hate this allergy season.

Anna: I have a question for you about, um, having gone through a, a, a big transformation and how you in your personal style and how you present, um, kind of post pandemic compared to pre pandemic. When you are gonna see someone that you haven't seen in years, do you say something to them about it beforehand? Or do you just show up? 

Bill: It depends. I feel like if I'm more nervous about seeing somebody, I'll send them a picture. Like, for example, I didn't see my parents for about a year, maybe a year and a half. They saw me– the last time they saw me was beginning of 2020. And I had only been on hormones for a couple months and they knew I was trans. Um, but I didn't really look different. So the next time they saw me was October 2021 for an art show that I was having. Um, they didn't know that I was getting top surgery until afterwards. So that was a big change. Um, but I sent them a few pictures and then… I don't know, uh, there was, there was a lot of anxiety around that.

Anna: Mm-hmm.

Bill: But other, other people that I haven't seen that I know I have a very solid relationship with, I love not sending pictures, and then trying to put together the best outfit I possibly can. And doing the sort of jump, the jump, you know, like here I am! It's like, it's like showing off a new car or something where you're like, Ooh, look at look at the body, like, look at the curves. Right? Look, I'm flatter everywhere. Like how crazy is that? Just having someone scream at you about how handsome you look is just, it's an amazing feeling.

That’s Bill Walker. You can check out his artwork on his website, lonesomebill.com. And you can hear Stephen Antony Beasley’s music on SoundCloud, and on podcasts, like NPR’s Invisibilia. And to see how he is a community-building fashion icon, his Instagram handle is in our show notes.

Thank you to all the listeners who shared your stories of personal style transition with us… you have each given me a little more courage to stretch beyond my go-to jeans and t-shirts. I salute you.

Death, Sex & Money is a listener-supported production of WNYC Studios in New York. This episode was produced by Afi Yellow-Duke. The rest of our team is Liliana Maria Percy Ruiz, Zoe Azulay, Lindsay Foster Thomas, and Andrew Dunn. Our intern is Lilly Clark. And special thanks to Julia Furlan for her help on this episode.

The Reverend John Delore and Steve Lewis wrote our theme music. 

I’m on Instagram @annasalepics, that’s P-I-C-S, and the show is @deathsexmoney on Twitter, Facebook, and Instagram. And if you are on Instagram anytime soon, and you have a photo of your personal style changes that you’d like to share, tag us! We’d love to see it and share it with others.

Thank you to Michelle Sanders in Belmont, North Carolina for being a member of Death, Sex & Money and supporting us with a monthly donation. Join Michelle and support what we do here by going to deathsexmoney.org/donate.

Bill: I mean, all clothes feel like drag, so it's like, oh, today, do I wanna be the like hunky mechanic that like knows how to, you know, wrench a, like wrench a car, right? Or I'm like, oh, do I wanna be like the beach himbo that's like super butch, but like also knows how to, like, throw a mean volleyball, right?

I’m Anna Sale and this is Death, Sex & Money from WNYC.