Transition of Style





Finnegan Shepard from Both& Apparel

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Finnegan Shepard, founder of Both& Apparel, joins the conversation this week to discuss the unique fashion needs of underrepresented communities, particularly the transgender, gender-fluid, and gender-free audience. Tune in to learn about the particularities of fundraising as an underrepresented founder, especially in early-stage fundraising.


Rocio Sanchez: Welcome to Transition of Style, the podcast about fashion, identity, and how queer leaders today are disrupting the fashion industry. I’m your host, Rocio Sanchez, pronoun indifferent, and a digital marketer with a specialization in queer business. I’m so interested in LGBT fashion, I wrote a whole master’s thesis about it. And I want nothing more than to bring my findings to you, the people I wrote it for. The LGBT community is no longer a footnote in the fashion industry, when we’ve been setting the trends all along. Our community today is paving the way like those before us did. And a prime example of that is today’s guest, Finnegan Shepard. Finnegan is the founder and CEO of Both& Apparel, the go-to brand for building your gender euphoric wardrobe.

Rocio Sanchez: You might recognize the brand name from features in Refinery 29 or Bloomberg. And like many great ideas, this one starts with a story. And here to tell it himself is Finnegan. 

Rocio Sanchez: Welcome, Finnegan. How are you today?

Finnegan Shepard: I’m doing well. How are you?

Rocio Sanchez: I’m doing good. Thank you so much for being here. So I would like to know, first off, how did you develop your style and how does it relate to your personal journey around who you are inside versus how people see you?

Finnegan Shepard: I would say like many people in the community that I’ve spoken with, my style has taken a lot of different iterations or shapes over the course of my life. I conducted one interview early on in Both& where a community member was talking about, style really as a form of character and I think that as a young trans person who didn’t really have the language for it, that was very much true for me. In the sense that I would sort of fixate on a particular figure, whether it was in a picture book or a movie or a friend at school and I would kind of make their style archetypal.

Finnegan Shepard: Because that felt like the most direct route to an expression of gender identity that didn’t need to explain itself. Like archetypes are so simple in most ways. So I think for much of my life, I cycled through these different archetypal styles in an attempt to feel that I was able to express myself or sort of translate myself to the outside world in a way that felt accurate to me.

Finnegan Shepard: And I would say, it always felt useful and successful to a certain degree, but there was also always an element of sort of cognitive dissonance. The one I talk about most frequently in interviews is this break dancing teacher I had when I was, I think 13 or 14. I really became fixated on these baggy Levi’s he wore , to the extent to which I felt like if I just got those pants, then not only would I look like him, but I would essentially become him.

Finnegan Shepard: And that was this like real light bulb moment of, got my mom to take me to the store and I tried them on and I was in the dressing room and really seeing that difference that like, no, it wasn’t him looking back at me in the mirror, it was just me in pants that didn’t fit me. I think, if I were to go back to a moment that planted the seed for Both& many years later, 

Finnegan Shepard: That was a pivotal foundational moment for sure. Because I think where I land today is, while I think style and self-expression is fascinating and wonderful and the queer community is often on the frontier of pushing that, and where I feel like I fit in comes really first from a value proposition that you have to begin with fit, and that style then can be built off of that. But that really what was missing my whole life was something very simple, which was just that, when I’m standing in that dressing room, I can’t get a pair of pants that are both the right length and fit around my hips.

Finnegan Shepard: And that’s not rocket science. That’s just changing proportions so that you can have a system that fits your body.

Rocio Sanchez: how would you describe now your archetype?  How would you describe your style now then?

Finnegan Shepard: I mean, ironically, I completely let go of any archetype or style pretty much at the exact same time as I started Both&, because I had recently started T (Testosterone), I’d had top surgery and it was COVID. And so like many other people, through a combination of being in lockdown and then also sort of feeling like, well, my body’s gonna change and I don’t really know what it’s gonna be like a year from now or three years from now.

Finnegan Shepard: Just like completely stopped shopping or even really getting dressed. And so there’s definitely an irony that for the last few years I’ve been on all these calls. There are elements that are coming out and like, I occasionally get dressed now, but I wouldn’t say I have an archetype right now. I would say I dress in a lot of Both& which fits me. And so that’s kind of an archetype in itself, but I don’t really feel like there’s a quote unquote character that I’m aiming for these days.

Rocio Sanchez: so I would love to shift more to the business side of it. So you’ve talked about gender free, gender euphoric clothing that really emphasizes fit. And you mentioned that for you it started from the point of, you had the problem yourself and then you set out to solve it. So that’s the need. 

Rocio Sanchez: Now that you’ve addressed that need and provided kind of a solution for it, what else do you think allows people to connect with it? Because people are really responding to it. Why do you think people are connecting with it?

Finnegan Shepard: Yeah, well the simplest and first answer is that there is a genuine need and gap in the market, and we are filling it. Like I get a lot of credit for how effective our marketing is, or how well our ads convert or whatever. And then I talk to advisors or investors and I’m like, you could credit me for, you know, headlines are creative, or you could just realize that rather than most brands which create something and then need to fabricate a desire for it, I’ve created something that people actually want and have been waiting their whole life for.

Finnegan Shepard: And sure there are hurdles, you know, do they trust me? Can they afford the price point? There’s all sorts of things that go through the consumer’s mindset as they encounter Both&. But at base it’s like, yeah, we’ve created a high quality product that actually solves a need that is resonant for a lot of people and that’s why it is resonating. 

Finnegan Shepard: At a brand level, it was interesting that you used the word gender free. I see Both& as occupying a really different space than what the majority of queer brands are talking about online. queer brands and/or mainstream fashion that is sort of getting into designing for quote unquote gender nonconforming or non-binary people. 

Finnegan Shepard: So when people say, when they label Both& as like agender or even non-binary wear or gender free or for every body or whatever, I’m like, not what we’re going for. That’s great if that’s what other people are going for and other brands will serve that need.

Finnegan Shepard: What I am serving is the belief that there is a group of people who are not looking to, just wear infinitely baggier clothing or, quote unquote, like cross dress or whatever that means in it’s queer connotation, but that people want clothing that fits their body in a very specific way, creates a very specific silhouette and creates a gender joy associated with that.

Rocio Sanchez: Euphoria, right? that’s really what jumped out at me that I haven’t really seen with other, brands specifically, and I feel like that’s what is working. So I was wondering, moreover, now that you have this and it’s working and you’re getting features left and right. I wonder what your biggest struggle is right now as a queer entrepreneur, queer leader in fashion, if that’s what you wanna call yourself.

Finnegan Shepard: Biggest challenges all have to do with what I think is a pretty natural discrepancy in the startup world between, how resourced slash capable you are of taking care of how many things are asked of you in any given moment. And you will always lag behind. The nature of a startup is that you are growing rapidly.

Finnegan Shepard: You are kind of constantly in a state of fundraising to be able to even stay alive or viable as a business. You’re impacted by market conditions. There’s all these outside economic things. And then, while you are putting out literally a thousand fires every single day, you are also wanting to keep your north star of like, what is it that makes me wake up in the morning and do this? What is the impact I want to bring to this community?

Finnegan Shepard: How you keep that front and center while also just surviving is also really challenging. And the reality is the faster you grow, the more attention you get. And it’s not all good attention. There’s transphobia and then there’s also just pushback of, I think people in the community are seeing Both&s rise and they’re feeling like, finally, here is this brand in this space that will listen to me or my needs and ergo, I have a right to express all complaints or desires to this brand, even if they’re not yet capable of meeting all these needs. And I think unless you are the person building the business, you don’t realize that values run in direct contradiction to each other. To have an accessible price point runs in direct contradiction to having not 8 sizes, but 20 sizes. 

Finnegan Shepard: To be sustainable or ethical also runs in contradiction to an accessible price point. To have more styles available, to have more ranges, to do collaborations with other, all of these things are wonderful things, but as a business owner, you have to really decide what hill you’re gonna die on.

Finnegan Shepard: And you can’t die on all of the hills and every person is gonna want a different hill for you to die on. And as somebody who takes it really personally, because I do see what I’m doing as so much a stewardship for the community and, and advocating on behalf of the community and wanting to create something that we’ve all been waiting for.

Finnegan Shepard: That’s a real growing pain for me right now, is learning how much I need to have a thick skin and not take complaints or critiques. It’s not, don’t take them seriously because obviously you want to always be aware of, of how people are thinking about things or what you should prioritize but, when you haven’t been paying yourself for years and you’re busting your butt to build something for the community, and someone comes along and just thinks that you’re like a filthy capitalist trying to get as many pennies from them as possible, you’re like, you have no idea what is going on behind the scenes or what it takes to build this.

Finnegan Shepard: It’s hard to not go into sort of emotional spirals around that. So yeah, I would say the biggest struggle is making the decisions I need to make for Both& to exist, period. Because if Both& doesn’t exist, then I can’t serve anyone. And then within that, what are the hills that we die on? And how do we be as strong and grow as strong as possible and serve as many needs as we can within these external macro economic factors that define our abilities.

Rocio Sanchez: Lots of moving parts and the struggle of kind of meeting the standards of the people that you do this for, that is the North Star. You’re doing it for those folks and yourself in, in a deeper way and matching that with your own standards. And also me personally, I, I struggle not in the same exact way where I have products and stuff, but in the same way where I am an entrepreneur and I’m a marketer that is intrinsically part of the capitalist system. I have my own values, but I’m also trying to survive. I’m also an immigrant. I’m also trying to say, hey, government, I’m making enough money to justify being here. 

Rocio Sanchez: It’s really a struggle and you can’t afford all that time online telling people that in an Instagram message.

Rocio Sanchez: So you cannot, so you walk away. And so for you, I’m sure it’s a whole other can of worms that you can’t, you literally can’t mentally go through that, especially with all the attention that you’re having with Both& at the moment. So, values, standards, all those things and that is something that already sets you apart from, these bigger brands that are pink washing and greenwashing and all that stuff. Yeah, they may go through the same things right now where everything is contradicting values, but at the very least you can say, or you can strive for integrity. Not kind of touting it and bragging about it, but you’re striving for that. 

Rocio Sanchez: And that’s kind of what I have seen among the people that I’m reaching out for, for this podcast and talking to them, is that that North Star is integrity and truly just trying your hardest while also surviving yourself and taking care of yourself. That is a huge thing that people really, really struggle with.

Rocio Sanchez: All things considering. All those struggles, those contradicting things, those hills. What are the trends that you see developing in your industry? 

Rocio Sanchez: Anything that you see happening in the finance that might affect you or just production or logistics or even marketing or just the way that we speak about it. Pop culture, what trends do you see developing in your industry?

Finnegan Shepard: So I’ll, I’ll try and answer this intelligently but, I would also step back and answer almost on a meta level first, in the sense that I think when, going into this as an outsider to all of these industries. To entrepreneurship, to business, to fashion. I really was naive in believing that there were answers or even really solid best practices.

Finnegan Shepard: And I think I had a lot of imposter syndrome and I spent a lot of time trying to find the people who were like the real experts who could tell me how to do things. And what I have realized over the last two years, and I mean this both in a really empowering way and also in a really frustrating and disempowering way is that, it is entirely made up. All of it is made up. 

Finnegan Shepard: And everyone is faking it and just telling as articulate of a story as they can, as they go along. Whether that’s in something that you would think would have to be really solid, like financial modeling. No, everyone is making it up. The story you tell in fundraising completely, like, and everyone agrees to it. You walk into these rooms and everyone agrees that you’re just making up a story and you’re co-creating the story together, and you decide if the person will buy it or not. When it comes to marketing, I get inundated by probably a hundred emails every day from a marketer who has the answer of, you know what, we’ll double revenue every night.

Finnegan Shepard: And like, it’s not that there aren’t arguments behind any of these strategies. Paid is dead, you can’t track it, get away from paid. Brand ambassadors are where it’s at. SEO and organic is where it’s at. Instagram is dead, move to TikTok. Actually, maybe TikTok is gonna be like kicked out of the US. Maybe don’t do TikTok. Literally everyone has their approach or answer. And I think the reality is as a creator, you need to walk this really challenging line of not wholesale rejecting best practices or the hard worn lessons of people who have done this before, because you would be silly to always reinvent the wheel and you won’t survive if you always reinvent the wheel.

Finnegan Shepard: But you need to take like every wheel with a serious grain of salt, and test it as cheaply and as quickly as you can, and be really good at figuring out what worked and what didn’t, and then developing your own opinion about what the next thing is. Because there just is not a formula, and that is what the act of entrepreneurship is. Is you just wake up every day and you be as creative as you can in plugging in these well-intentioned attempts at moving the boulder like one inch further up the mountain. And some days you get crushed and you roll down like 10 feet and some days you’re like, whoa, I’m on fire, and I just went up 20 feet. 

Finnegan Shepard: It’s a game in, in stamina and endurance and in listening to others and in thinking critically about like, well, that worked for them, but that’s not gonna work for me. Early on I had these people who I really admired who come from sort of corporate fashion world. 

Finnegan Shepard: What they said, I took as gospel of like, whoa, like if that works at the top level of Nike, oh my God, who am I to assume? But it’s like, of course what works at the top level of Nike is totally different than what works for a startup two months in with like three T-shirts to sell. Its literally an entirely different market.

Finnegan Shepard:  So I realized that didn’t really answer trends so much as like, I think the macro trend is that as humans, we always want a solution. And we always want it to be simple. But the reality is like if there was a simple solution, everyone would do it. And the hard work is the fact that you’re gonna have to piecemeal it together, you’re gonna have to come up with your own patchwork solution. And that just requires a lot of openness and resilience and endurance and creativity.

Rocio Sanchez: Intuition is such an important part of it, and that intuition is almost like a skill. Some people can say they don’t have it or they do have it, whatever. But when you’re in this role that we’re in, every day you make a bunch of decisions. At some point you have to let go.

Rocio Sanchez: At some point you just assess what you have and understand, oh, I don’t know, X, Y, Z. But let’s put it in and let’s see what the output is, and then we’ll figure out retroactively what X, Y, and Z is. It’s really something that is really hard to let go on. You work on it every single day. Was that the right decision? Was that not? And so I feel like that is something that is tale as old as time, honestly, but it still rings true today. And I love what you said about, we’re all just kind of collectively making stories in these pitches in these rooms I just feel like we’re in the golden age of scammers, we have FTX, we have Silicon Valley Bank, we have. Well that was years ago. We have Theranos. Right? 

Rocio Sanchez: And it’s just all this stuff is, and then you, you hear about their stories and they just walked in and they just said the thing, like, they just said the thing and everyone was like, cool, we’re on board.

Rocio Sanchez: So those are the things that make me go okay, well these people obviously lacked integrity, right? They kind of got carried away or whatever it might be. But it just shows that, if they could do it so can we. Not the scamming part, but the getting to a point, 

Finnegan Shepard:  We’re kind of set up for failure as founders to a certain degree in terms of integrity in the sense that we cannot survive unless we have unwavering faith that we will somehow figure it out.

Finnegan Shepard: But like, of course we haven’t figured it out yet. And that is why we are fundraising. That is like why we are in this process of like trying to keep something alive long enough that it can figure itself out by curtain call. And there’s a lot of different ways to run that and certainly shades of morality or the story that you tell. But with underrepresented founders especially, there’s this article by this woman Katherine Finney, who invested in Both& who’s doing really cool things, she’s the leader of Genius Guild. And she wrote this really beautiful article about, with the market downturn, one of the issues we see in fundraising is not just the underrepresented founders don’t get access to capital at the beginning, but then when the market turns down, you see the VCs, they stand by the white cis men. And they don’t do the bridge rounds, they don’t back these underrepresented founders in the harder times. 

Finnegan Shepard: So it’s sort of like if you can be extraordinary and as long as things are going really well, then you can sometimes squeak through the cracks. But what runway is, what fundraising is, is not that you have figured it out. It is the grace that we believe in you enough that you will figure it out.

Finnegan Shepard: And I think that switch in my mind of like a, early stage founder who has all this imposter syndrome and like, I’m not selling $10 million a year yet, I’m not like worthy of this money or whatever. It’s like, no, like early stage capital is not about you proving anything.

Finnegan Shepard: It’s about having faith in you and the belief that you’ll figure it out. And there is such a discrepancy in how much that kind of faith goes to underrepresented founders versus more traditional founders. So yeah, we really went down the fundraising route there, but it’s, it’s a thorny issue.

Finnegan Shepard: It’s a scary issue. To the trends of the market right now, I think it’s like an even more hyperbolic version of what I’m saying in general. It’s like, I think it’s always been story making. I think it’s always been challenging in soul wrenching for founders. Even like the cis white males who graduate from Stanford. I think it’s easy for us to say like, oh, it’s so easy for them, they just like graduate and have 10 million dollars. Literally every founder I’ve ever talked to says a part of their soul dies when they fundraise. It’s extra hard if you’re underrepresented, and it’s extra hard if you’re in an industry like fashion. 

Finnegan Shepard: But the reality is it’s not fun or easy for anyone, I don’t think. And in a market like this where things are so uncertain, and it’s every day people are like, are we in a recession? Are we not in a recession? What is happening? Like, the trend right now is just, I think taking that baseline uncertainty and that things are always kind of made up and unstable to just like the nth degree.

Finnegan Shepard: And fundraising is really messy right now.

Rocio Sanchez:And you spoke to another struggle which is just, people kind of starting out strong for underrepresented communities and then when things go south, that faith waivers a little bit and people back out. And so that is just not what needs to happen for things to continue growing as they are.

Rocio Sanchez: It doesn’t have to be incredibly individualistic as much as the system has made it out to be. That we’re kind of on our own and pulling ourselves up by the bootstraps. Our community has shown that we don’t have to do that, and that historically it’s never been just one person, but rather a whole group of people. So who would you say is besides the people that you’re creating this for, like who is your community that has helped pull you to this point?

Finnegan Shepard: I’m incredibly blessed with my kind of foundation of friends and family and my partner. I think not infrequently about the fact that my resilience and capability of building Both& is not not related to the fact that the rest of my life requires very little emotional labor or. I don’t know if I could have built Both& if I was kicked out of the home by my parents or if I didn’t have a loving and supportive partner, or that I didn’t have, you know, like my team for the first year of Both& were literally just the friends I knew who had skills that could help and didn’t need any money to do it, and like believed in the vision enough. So it really, it takes a village. It takes an army of people who, both the people who will, my CFO, he’s one of my best friends since I was five years old. He still hasn’t taken a dime from Both&, and we’re like three years in and like on top of his nine to five job, he has handled our finances and a lot of our operational stuff just like day in, day out because he believes in Both& like, he’s, he’s gonna do that and like, I couldn’t have done it without him. Same with my wife. At the end of the day, I get to come off a meeting and be spinning like a top and go out there and go on a walk with her and like decompress and get her to sort of ground me and, and see me in, in what I’m going through and countless people who’ve supported me. The idea that founders do it by themselves, I think is, I mean, I have yet to ever meet a founder who does do it by themselves. I don’t think it’s actually possible.

Rocio Sanchez: That goes back to just being able to ground yourself and find the moments of peace in this wild, wild environment that we’re at. Where when we’re doing what we’re doing seemingly everything is at odds with another value that we have. And so sometimes, especially online, we have this discourse of just, black and white issues.

Rocio Sanchez: And yes, maybe, we could talk about that. But at the end of the day, we need moments of peace. And if that’s just going out for a walk, that’s what I love to hear at the end of the day. So, I really, really enjoyed this conversation with you. Is there anything that you would like to sign off with to let people know?

Finnegan Shepard: I mean, something that you point to in that last phrase, and I feel like has been somewhat of a theme of what we’ve talked today is like. I believe in a philosophy at Both&, and that’s why it’s the name of the company. And I think unfortunately we’ve found ourselves in a bit of an intellectual cul-de-sac online.

Finnegan Shepard: I think that all of these issues are far more rich and interesting than we give them credit for. And that unfortunately, we’re kind of creating a world that prioritizes a binary thinking even as we claim to be fighting against it. I would just say, you know, that’s my hill I die on ultimately. That’s why I’ve named the brand Both&, and whether I’ll ever be able to pull it off effectively and how a brand shows up, and as you know, as a marketer is like, it’s always compressed spaces and there’s always competing needs. But at the end of the day, if that’s the impact I can leave is like in my small way, to leave a legacy of Both& thinking, then that’s what I hope to do.

Rocio Sanchez: Thank you so much for ending on that note, and would you like to tell the folks where they can find you and anything exciting that’s going on?

Finnegan Shepard: Yeah, so you can find Both& and on TikTok and Instagram at @bothandapparel. I personally have a website, I don’t do much there. The latest thing going on for me is I co-wrote a play that got into the New York Theater Festival, That’s a little, little side thing. And I also run an Entymology newsletter. That’s the other thing I recommend. Diversify your hobbies and interest. It keeps you more sane. Even if you’re founding a company, like carve out a little time for things that are an end unto themselves.

Rocio Sanchez: Well thank you so much for joining 

Rocio Sanchez: and I will see you around the next time. 

Rocio Sanchez: Transition of Style is brought to you by FC Podcasts, a division of Fashion Consort. Learn more about how FC Podcasts can help you with podcasting, from strategy and creation, to production and marketing at That’s Thank you FC Podcasts, for making Transition of Style possible. 

Rocio Sanchez: Now, back to the show.

Rocio Sanchez: Welcome back to Transition of Style. It’s time for the case study portion of the episode. Today’s case study is about the power of market research. Understanding your audience is one of the most important aspects of owning a business.

 As a direct to consumer company, it’s clear that the team behind Both& Apparel has made great efforts to not only hear the audience’s needs, but to address them as well. This is no more apparent than on the Both& Apparel website. The Both& website mentions how a ton of research went behind the production of the products.

 While the detailed quantitative results of the surveys are not publicly disclosed, we can tell from the product pages and reviews how closely Both& Apparel answers the unique needs of its transgender, gender fluid, and gender free audience.

Rocio Sanchez: No “bunching at the hips” for sweaters, which may be a concern for people who don’t want to emphasize their hips. On another product page, a t-shirt is distinctly described as having ” raised collar covers to cover binder lines.” For those who don’t know, chest binders are used to conceal the appearance of breasts and are worn usually as an undershirt.

We heard in this episode how founder Finnegan Shepard saw an answer to his own question, and then continued by quantitatively answering it for thousands of other people.

So what are the three takeaways that we can take from Both& Apparel? One, don’t neglect market research. This is kind of a no brainer, but it seems to be something that businesses sometimes forget. But, also remember that market research could also be as simple as networking and coffee dates with your target audience. Or, it could be as robust as a survey. 

Two, don’t make up a story before the market research tells you a story itself. Now, in Finn’s case, his story is very clearly aligned with thousands of other people’s. But the key here was that he still did the research.

Rocio Sanchez: Three, spell it out or don’t. If you’re a fashion e-commerce brand, depending on your brand voice and image, you might want to spell out exactly why your product is better. Or you might not want to for fear of ruining your brand image by not letting the work speak for itself. There’s no right or wrong answer here, and it really depends on the brand image and the brand voice. But being upfront about what the fit is like seems to resonate a lot with queer and trans audiences. And I assume that’s why this aspect of Both& is so clear on its website. 

That’s all for today. If you liked my insights on market research, I actually have a blog post on queer market research where you can learn more from my marketing expertise.

Subscribe to the transition of style newsletter to get ahold of it on Thanks for listening and I’ll talk to you soon.

About Finnegan Shepard

Finnegan Shepard (he/him) is the CEO and founder of Both& Apparel, a genderfree e-commerce clothing brand that seeks to profit comfortable fit to its customers. With a background in philosophy and writing, Finnegan brings his lived experience as a trans-man to the world of entrepreneurship and fundraising, discovering unique hurdles along the way. Despite this, Finnegan Shepard allows his customers to experience gender joy through Both& Apparel.


Rocio Sanchez, host and producer
Caitlin Whyte, audio engineer
Sophie Jacqueline, video editor

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