All Work and No Play? Think Again: an Interview with Play Out Underwear + NYC PRIDE TIPS

Liz Leifer, Chief Creative Officer and Abby Sugar, Co-Founder of Play Out

Liz Leifer, Chief Creative Officer and Abby Sugar, Co-Founder of Play Out

NYC Pride is just days away and WERKIN is thrilled to be a part of the local LGBTQ+ community of businesses. WERKIN’s own Alex D’Sa, People Experience Lead, sat down with Abby Sugar, co-founder and Liz Leifer, Chief Creative Officer of Play Out Underwear, an NYC-based inclusive underwear brand.

Alex D’Sa: Thank you so much for doing this interview with us! Play Out is such an incredible company. What was your journey starting this company?

Abby Sugar: So I founded Play Out with an ex-business partner; we launched officially in 2014 at Lingerie Fashion Week in the Fall of 2014. We had an amazing reception then, and still to this day I think queer fashion in the past just 3 or 4 years has really exploded. When I was doing it in 2014, not a lot of people were paying attention to queer fashion and I got a lot of questions along the lines of, “well, what do you think of this trend?” and my answer was always:

This isn’t a trend. This is who we are.” We’re doing this because we couldn’t find fashion or underwear specifically that we were comfortable wearing, that made us feel sexy, that was gender-affirming, sexuality-affirming, human-affirming for who we were and how we wanted to express ourselves.

Now there are a few other brands doing it and a lot more design happening which is amazing because you want everyone to be their truest selves. In 2015, we also did a photoshoot series with “young” (and I say young meaning “diagnosed-with-breast-cancer-under-the-age-of-45”) breast cancer survivors who had had double mastectomies without reconstruction. And similarly, when we did this photoshoot in 2015, that was a conversation that a lot of people weren’t having. One of our friends was 31 when she was diagnosed, and she was queer, and so it was this intersection of queerness/gender identity/healthcare/breast cancer/assumptions of what a woman should look like… and underwear... because it’s intimate.

It was interesting because I was really good friends with Liz at the time, and we weren’t business partners yet. Liz has her own journey with a preventative double mastectomy. That was 2015, and my business partner and I went our separate ways in 2016 and Liz joined me in 2017. And here we are!

Liz Leifer: And I can’t believe we just had our two year anniversary as business partners!

AD: Before we get to Liz joining the team, how did the journey start for you?

AS: My ex-business partner and I came up with the idea together. It really came about because my business partner, could not find underwear that she wanted to wear and was comfortable wearing. I spent hours, days, trying to find affordable underwear that was active and stylish and fun. I like using the word “active” because I think women are portrayed as passive a lot. Men’s underwear gets superhero designs, and trucks, and car crashes(!) and I’m thinking... “well why isn’t everything available for everybody?” So I spent hours trying to find this. In 2011-2012, when I first started researching, there was nothing. It was Victoria’s Secret, and super lacy lingerie. So we had another conversation and I said “we have to make this” and we were both just crazy enough to do it.

I had no background in fashion. I’ve now been doing this for 7 years. So I know what I’m doing: I know my sourcing, I know my supply chain, I know my job. But in terms of getting started it was a lot of learning, connecting, networking, mentors.

AD: Did you have any notable mentors at the start of your journey?

AS: Not mentors so much as helpful friends. So one of my friends who’s the ex of… that’s another thing about being LGBTQ is that the community is really small and the community also consists of a lot of your exes! One of my dear friends, her ex-girlfriend is a costumier on Broadway. So she was one of the first people I talked to about where to start.

Actually, I would say that I had a bit of a mentor. I met mine through my alumni association. I went to Barnard College, and when I was first starting to work on this idea I started going to more networking events. Someone I spoke with asked if I knew someone who happened to be a notable alum of the college who is very high up at a successful underwear company. I had no idea who they were.

So I sent her an email through the alumni network along the lines of: “I’ve done nothing, I’m trying to learn, etc.” and she was super encouraging and invited me to come and visit their offices and their showroom and some of their manufacturing facilities. And since then we meet up at least 3 or 4 times a year and update each other. She’s just been amazing to talk to.

AD: Do you feel in that sense you have something to offer her as well?

AS: Absolutely. Sometimes we just sit there and go “these problems, they’re the same”, but she’s at a much grander level.

When people ask me how to find a mentor, I always say alumni groups. Being in New York, in fashion, in NYC, in London, in Paris… when I decided to do this it was “oh, go take some classes at the Fashion Institute of Technology”, “go to the garment district and have meetings with people.” Having access to that stuff is significant. And then Lingerie Fashion Week launched. We just figured it out. So that’s my personal motto:

“F*cking Figure It Out”

AD: Great. So we get to 2017 and Liz joins the team… how did that happen?

LL: Abby and I had been friends socially for years and we were kind of spitballing and I was doing some brand consulting for her: what are the next steps? Where do you want to take this next? She was shopping for a new business partner anyway. Behind the scenes, I was at a place with my corporate job where, on the heels of what’s been happening with our current administration, I definitely was feeling like I wanted to do something that was more of service to my community. And so when we were having this conversation, we were in such alignment that it was so… organic, and it was really clear that we both had a very strong vision of what this company could turn into with the right business partner and the person who could share that vision and the strengths that were needed to complement Abby’s strengths and as we were talking about it we were kind of like… “or… I could do… it? Maybe? What?!”

It just made so much sense that it seemed it would be stupid not to. When the universe puts something like this in front of you, she’s just saying “I can’t make it any simpler for you people, just do it!”

AD: Did it occur to you beforehand when you were consulting or did it happen right then?

LL: No, it just happened. This was the pivotal conversation. And then everything just steamrolled from there. And as soon as we signed paperwork and made everything official, we made our marching orders of what we were going to update - our website, shopping platform UX, everything from the ground up. So we set out on a mission to accomplish all these goals, to find new sourcing for all of our materials, how they were constructing, who was constructing them with us and did all of that in just about a year. And we had a big expansion, an explosion of offerings in more styles and designs in a wider size range… we came so hard into our new product line.

LL: And we had seriously been going non-stop. It was another probably 7/8 months before I left my 70 hour a week job. And it was really organic, it was totally meant to be. And it happened in one of those ways where you couldn’t orchestrate it better.

AD: It’s a big thing to make that leap from the corporate world. Did you have anyone who you sought advice from?

LL: I did. I have different people in my life for different subject matter. The person I go to for business advice is not the same person I go to for love advice (laughs). And I had a mentor when I was at my corporate job, and I chatted to them and I had a serious sit-down and said: “These are the things that are important to me, I feel like I can’t accomplish both of these at the same time. I can’t do it at this job.” They were very nice, “If you feel like you can be of more service doing something else, who am I to say no?” That is something that is bigger than any job you would have and if that’s what you want to be doing and that’s what you’re willing to sacrifice and risk for it then you should do it.

And that’s the biggest thing… and I say it all the time in interviews but when I was a kid, my dad said to me:

You will have moments in your life where you will have to risk everything you have to get what you want, and you have to understand what those stakes are and you have to be willing to put everything on the line to move to the next place that you want to be. Because that’s sometimes how opportunity presents itself.

My eight year old brain was chewing on it so hard, and I would ask him follow-up questions over the years… and then I started having moments in my life where I had to be really clear on what my bottom line was, what was my endgame and always have that in my sights. So no matter how tumultuous things are in the moment, or no matter how unsafe you can feel sometimes, always have your eye on that end goal.

AS: But I think that’s something I try to lean into as well. When I’m afraid of something or when it makes me really scared, but if I know that I’m solid in my core, then it’s actually the right thing to be doing. If I’m not scared about it, then it’s not actually going to make a difference.

LL: It’s not a legitimate risk. And there are risks that are appropriate to take. You’re not going to get ahead, you’re just not going to get to extreme levels that people get to in success without being a risk-taker, it’s just not possible.

AD: This mentor that you mentioned Liz, and your own bottom line, if they had said: “yeah I don’t think it’s a good idea, I think you need to stick at this job a bit longer.” If everyone was saying that, do you think you…

LL: I still would have done it. 100% I will seek lots of counsel. And I will take everything under advisement. I will weigh it out very carefully. But I will make a decision based on my gut. Because I have nothing else that is as true to me and knows me as well as my internal moral, ethical compass. And it 100% was ”We’re doing it!”

AD: And so what’s the next step for Play Out?

LL: We have been doing a friends and family round. We have secured our first convertible note that should come through soon and we’re going to use that to move to the next level so that we can advance our traction to go for a larger round. And we’re going to move into athleisure and activewear and be a lifestyle brand.

AD: Amazing! Are both of you into fitness?

AS: Well I’m a personal trainer!

LL: Athleisure is one of the largest growing sectors. People live in it, everyone wants to wear it all day long.

AS: The thing is, having had experience as a trainer, wearing gym clothes all the time… it does get old. I always felt, personally, like I was a slob. But if it was fashion, it’s a different thing. But also fashion for who we are - which is, gender-affirming fashion. The funny thing, the joke I always make, is you can go to a gym and look around and I can see either the tomboy athletes who may or may not be straight, versus the lesbians, versus the super-straight girls, because the super-straight girls are in the tight-knit spandex, and the crop tops or the sports bras. And the lesbians are in t-shirts and old sports team jerseys.

AD: I wear my old PE shorts to the gym!

AS: Exactly! And like men’s PE shorts. But if we can make that fashionable…

AD: And can people buy this soon?

LL: It’s in R&D right now and it really needs to be right because I don’t want to bring something to the marketplace that is on the heels of something else. I want it to be something that really speaks to gender equality. It’s about the artistry, the quality, the way that it is presented… it needs to be all access for people. I don’t want it to be something where we take a pair of sweatpants and slap a name on it.

AS: We’re designing.

LL: Creating the products. we have an amazing muscle shirt that we designed for World Pride actually, and it’s so great because it has a drop waist in the back. And it’s a traditional muscle-tee but it comes out to a point on the average shoulder where it’s really flattering to the upper arm and has a nice neckline that allows us to have pretty imagery on it. And it’s freakishly buttery soft. And I think it has to be a more overall fashion statement that you’re making.

AS: When Liz and I were aligned, it wasn’t just about the business, and what we wanted to do, it was also aligned on our aesthetics and style. And I always say this because it’s easier for me to promote everybody else… but a big part of what we do is prints, and a lot of those designs Liz hand paints - paintings that we then digitize and print on the fabric to make our underwear and some of our tank tops.

AD: So how do you have time to sleep?

LL: Not a lot of sleeping happens!

AS: Nope!

AD: So what do you do for self care?

AS: We both work out

LL: Yeah the gym makes me happy. That’s a nice re-centering time. Painting makes me extremely happy, painting for my own enjoyment. And I definitely let loose on the dance floor on occasion… at the ripe age of 49, I try to stay out at least once every quarter until 3-4am dancing, just to know that I can still do it!

AS: But you know, I work out at least 4 or 5 days a week. When I’m working out for that hour/hour and a half, I’m not answering my phone, I’m not answering my emails. I have to be in this moment. I’m also a writer, I read a lot. I take 20 minutes, I drink my coffee, I read or I do some writing to keep centered.

LL: I look at excessive amounts of art. I’m super visual. I go to museums or galleries or combing the Internet for artists I don’t know of yet and studying their work and looking at in general what’s happening in fashion. And for me because I’m so visual, that’s the stuff that sticks with me. I find things in the most interesting places.

AD: Do you have an LGBTQ role model? I have loads but I want you to pick one!

LL: Oh I need a second!

AS: I know! I go to writers… I go to Audre Lorde, I go to Adrienne Rich, I go to Maggie Nelson, who is a contemporary writer who is really amazing.

LL: Butler is huge for me.

AS: Oh yeah Judith Butler, the next person I was going to name!

LL: There’s so many people. Right now there are endless amazing people - Janet Mock. So many people making these amazing moves. I’m personally celebrating Pride by going to see John Cameron Mitchell on Broadway. He really made a massive impression on me at the time. When Hedwig came out in 2001, there was something about it - so much pain and so much sorrow that has translated into hope, and self-discovery. It was really eye-opening for me and he’s always been somebody… I don’t follow a lot of famous people on Instagram but I follow him. I’d be a total goober if I met him!

AD: What are you looking forward to most about Pride?

AS: We’ve been working on Pride Week a ton, and are two main things that we’re been participating in.

  1. The first is the dapperQ AirBnb pop-up space is having a big queer fashion presentation and panel. We’re one of five designers on the panel, with 7 underwear models. The topic of the whole night is Queer Fashion as Visual Activism, so that’s going to be really awesome. So that’s from 5-7pm on June 28th. It’s free, you just have to RSVP. There will be free wine and beer.

    At 6pm we’re going to have a panel discussion moderated by Anita, the owner of dapperQ which is a queer fashion website - the biggest queer fashion website in the US, maybe globally. Liz is speaking on the panel, and our models are going to be hanging around. I was in the space today, it’s a really cool space and the capacity is kind of small - 250 people; dapperQ does an event at the Brooklyn Museum that has around 2,000 people.

    RSVP and get there on time because there’s going to be a line!

    But AirBnb is doing this popup space and they have events the whole weekend, so we’re the Fashion Friday night programming and then they’re having a Queer Bazaar where queer makers can sell their stuff on Saturday.

  2. And then Sunday…

    LL: Yeah then Sunday I’m on the official Stonewall float which will be fun. And then afterwards we have models and the party starts (and possibly gogo dancers) at a party at the Jane ballroom after the Pride parade.

    AS: So for Sunday June 30, which is the official Pride March, we partnered with Wanda Acosta who is a legend in the New York City lesbian nightlife scene. She hosted a lesbian party on the Lower East Side at this bar called Cafe Tabac in the early 90s… she’s history.

    LL: Her invitations to parties and polaroids of her are in the NY Historical Society Stonewall50 show. We’re super excited to be doing this with her and to be the only brand working with her on this is awesome.

    AS: It’s Wanda’s party on Sunday and it’s taking place at the Jane hotel and we’re gonna have 5-7 underwear models in the crowd posing with people, dancing with people, it’s going to be really fun.

    LL: And that’s an all-genders party. So it’s great, we’re going to have super broad representation with our models.

AS: On Saturday, we’re going to the Pier Pressure Yacht party. Our friend Antonia, she and her business partners have a new website called QueerCut which is a new queer fashion website and marketplace. Antonia is also a party promoter and so QueerCut is sponsoring part of the party and is going to have us being one of the designers who have samples of stuff for people to check out.

And of course the LBTQWomen conference on Wednesday is going to be great!

Want to learn more about how you can build your business or career during Pride? Sign up to apply to WERKIN’s NYC WorldPride Mentoring program here.