Cher Strauberry is the Queen of Candyland

Cher’s influence on queer subculture isn’t limited to just being a glam-rock style icon or paving the way for LGBT skaters. When she’s not sailing through the Bay Area on her board, you might find her front stage with Twomsax — one of the many punk bands she has inhabited over the years. 

More recently — through pandemic-induced isolation and an old tape recorder —  her debut solo record “Chering is Caring” was born. With a handful of singles out now, the full album is set to release on June 18. 

The Cher colorway is available for purchase online now and in select stores, and check out our exclusive interview with Cher below.

Can you walk me through the moment when you first found out you had the opportunity to design your own shoes with Vans? What was running through your mind?

It was probably a year ago that I found out. I basically hopped on a call with them and they were like, “We're going to do collections about these people, and we want you to do one. Why don't you take some time to think about it and let us know what you want to do.” And I instantly was like, “No, I know exactly what I want to do.” I just ran to my closet and started spouting off crazy ideas. Originally I was like, “I want to do a slip dress. I want to do a cardigan. It's going to be cheetah print. It’s going to be lacy.” And they were like, “Whoah, we can't make all that stuff,” which was really funny. 

I kinda got to do my own spin on things. I had all the embroideries — those are all my stamps and my handwriting. The inside of the jacket I made has the little cut scissors with a dotted line so you can crop it, cause I wanted a big jacket but also want people to crop it and fuck it up really bad. I designed it all in a day pretty much. It was sick. I definitely never thought I would do that, but Vans is awesome and been so sweet and kind to me. I’m stoked to be a part of their team. So yeah, it was rad. I knew exactly what I wanted based on the clothes I had been wearing at that time, essentially.

How has Vans played a part in your upbringing within the skate community?

Growing up, I only skated Vans slip-ons. One of my favorite skaters growing up — his name was Ragdoll — only wore Vans slip-ons, so that's all I did. Then I went through my Nirvana phase super hard in the years I wasn't skateboarding, so I had Chuck Taylors. There's one lady I would go see at the Oakland Flea Market at Laney College, and she had pretty much only those shoes. Anytime I needed new skate shoes, I’d go and find fucked up pairs that were like five bucks. And then all of a sudden she was gone one day and I was like, “Oh no, she's gone. Where's the shoe lady? This sucks.” Cause shoes are expensive as fuck. 

How it all started really was I asked my friend Max — he's a vert pro from the 80s — I was like, “Hey, do you know anyone at Vans who would send me some shoes?” He sent me my friend Sierra’s email, and I emailed her and she was like, “Oh, I've already been watching you skate. I'll send you some shoes.” Then when I started working at Supreme, Converse reached out and was like, “We’ll, like, sponsors sponsor you if you want.” And I was like, “Yeah, sure.” Cause I wasn't part of the team or anything, they would send me shoes every once in a while. Then after the Supreme video came out, Vans hit up William Strobeck and was like, “We want her back on the team.” Basically, there was some back and forth between the two companies. But I told Vans, “If you match what they're offering me, I would rather skate for Vans,” because that's the company I liked growing up, and they were like, “Yeah, we'll do it.” I'm super happy I went with Vans because it's sick and they’ve helped me do so much. I've done so much stuff for them in the past year. I did a whole zine for them that's out now too. They're the best. I love them so much.

I saw that you said the cheetah print was based on the first skirt you got when you revealed that you were transitioning. Would you say that you have since adopted the cheetah as kind of a spirit animal?

Probably a little bit. I've been having this weird relationship to clothes, where sometimes I’ll go to a thrift store with my partner and I'm like, “I don't even know what I'm looking for.” And then we started looking through my closet and mostly everything I love has just been a hand-me-down from someone. It's funny cause I used to wear that cheetah print skirt, like every day, and I still wear it all the fucking time. It's the best cheetah print skirt. But my friend, Wavvie — we worked at a coffee shop together — one day we were talking and I was mildly trying to tell her I'm gonna transition. But she kinda figured it out before I could say it, and she had started crying at the coffee shop and gave me a hug. After work that day, she was like, “I’ll help you if you want help with anything.” And I was like, “I need help with everything.” 

She literally Naired my whole body that night and looked up all these places where I can go get hormones. And then she went through her closet and just gave me a whole new wardrobe. She gave me like five skirts and a dress, and I still have all of it. It’s still my favorite shit. She did all my little hand tattoos that I have too. She's really sick. So the cheetah print all comes from Wavvie. But I guess it's kind of become a thing for me cause I really fuck with it heavily. But also, I grew up with a bunch of older punk girls who all wore fucked up cheetah print skirts and bullet belts and shit like that. I always thought they looked so cool. So the cheetah print skirt had always been on my radar.

You clearly seem to be into fashion as a form of self-expression. Would you say that moment with Wavvie was when you started wearing what makes you happy?

Yeah, pretty much. I tried a lot of different things. There are old pictures of me from when I was like 17 or 18 and I was wearing fishnets and short skirts, so I was kind of already on that spectrum tip. But yeah, Wavvie definitely was the one who was like, “Let’s go get you clothes. I want to see the girl that you see in your head.” And I was just like, “Oh, well I'm ready for that now.”

When do you feel most confident?

Always Fishnets. There's always fishnets involved. I think it stays where I don't have to rush when I feel the most confident. It's fun to leisurely do your makeup and just hang. Confidence is a hard thing to come by honestly. It's very back and forth, and some days are easier than others. It's been a lot easier after I'm in year three now. The first two were really fucking hard. I don't think I ever felt confident. It was more like, “Fuck it. This is me. And I know this year is going to suck, but I got to start doing it now.” You had to really destroy what other people thought of you, which maybe is a thing of confidence. 

I wouldn't consider myself a super confident person, really. But I love my cheetah print skirt. Favorite outfits are my Courtney Love/Kim Shattuck from The Muffs, like, dress, fishnets, slip-ons. I've been wearing more girly-ass shoes now too. Just like 90s girl, thrift store, little heel sandals, which is nice to wear if I'm not skating. Working as Supreme was really hard to have to incorporate boy clothes into my wardrobe, and that shit left me feeling really dysphoric a lot of the time. So, it's nice to just wear whatever I want as opposed to having to go to work and incorporate something.

Being queer in both the punk rock and the skate world, do you feel like you've witnessed a shift towards inclusivity within these communities? And how has it differed between the two?

Similar in ways. More similar than you would think, but skateboarding definitely has been a fucking boys’ world. I didn't know. I was just skating with my Unity friends in the Bay Area and we had a very special little vibe going on, which it's not like that all places. I'd like to think it's getting better. There's a lot more out queer and trans people in skating. There were definitely times where I didn't feel accepted or I didn't feel like people were fucking with me in the punk-rock scene. But my band Twompsax — when we were touring it was my favorite tour experience of all time.

We only got to do one tour before the pandemic started, but we did a whole U.S. tour. Literally everywhere we went, it was just queer punk people and that's who we were playing for essentially. In every town, I met at least five to 20 trans people at every show who were super stoked. I think as a unit, our band was really confident. I definitely feel like — talking about confidence — being behind that microphone at a Twompsax show is when I feel most confident. Cause with a punk-rock band behind you and a mic in your hand, I will fully fight for what we deserve and I’ll win. 

But yeah, I think it's changing a lot. It should be, and it's time for that. Surprisingly with the music stuff, I didn't get very much bad feedback. Some shows were super crazy and a lot of people, and some were like 10 kids in a basement and it was still wild and super fun. You can tell the message that we were bringing — there were definitely kids in towns who had never heard that. It makes you feel like you're doing something important. When your music actually has a message, it's pretty powerful. 

Speaking of music, you have a new album coming out called “Chering is Caring” which you describe as a “mixtape of my life from the past two years.” What's something that has inspired your songwriting for this album?

I've always written little acoustics songs. I love playing acoustic guitar. I’m a total indie rock, K Records nerd. But I super got into this album from Beck called “One Foot in the Grave,” and it goes all over the place. It goes from what sounds like was recorded on someone's answering machine, to just singing, to a full band song, to just scratchy noise nonsense, to a really well-written acoustic singer-songwriter song. When I heard that album probably five or six years ago, that always stuck with me really hard. And I was just like, “I want to make something like my own version of this.” So that's what I was kind of thinking when I put it together. But I also didn't really realize I was writing a record when I was doing it. I just always have my tape player and always record shit. I'm always writing songs. I don't really think about it too much. I try not to think about any art or anything too much. I try just to do things.

Was there anyone you looked up to as a young musician/skater?

I like left the skateboarding scene for a really long time. So when we started doing it, I wasn't even aware of other scenes. I didn't watch skate videos for like 10 years, 11 years. I fully just fell off with it. Elissa Steamer always was a huge influence just because she was so sick. She was one of the only girls that I ever saw who had parts when I started skating. My friend, Leo Baker, he's a trans boy now but we skated in the same contest league when we were growing up. It's funny cause I used to skate for the boy’s division and he used to skate for the girl’s division, but now we have a company together. We're the same age, so I was always aware of him. I thought he was sick cause he was doing really hard tracks and crazy shit at the skate park. That was when I was really young. 

And then music — pretty much my friend Brontez who has a band called the Younger Lovers was my biggest queer influence. I saw one Brontez show when I was 14 or 15. It just made me fully come out and be queer and just start playing music, because he definitely does not give a fuck what anyone thinks. He's amazing. But there's not a queer musician really that I was looking up to specifically. I liked ‘G.L.O.S.S.’ and ‘Limp Wrist,’ but I'm more so just like, “Their music is great.” Just knowing there were two queer hardcore bands, I was like, “We need another one right now. I want to do it crazier and more trans apparent.” Just knowing that there were other bands doing it, I was like, “Okay, sick.” But I knew they were older than me too, so I was like, “We need one, like, now.” 

As a trailblazer in the skate community, what do you have to say to the people who now look up to you?

It's so crazy to think of that. I have so many messages. My Instagram DMs are at 99 plus and have been for like two years. They range from kids being super excited and telling me their life stories, which are really cute honestly. Then it goes from people being so pissed that I exist. I've gotten tons of death threats and people saying the most horrendous things. But I always tell the kids the same shit — just follow your heart and follow your dreams. Cause maybe kids’ parents don’t tell them it's okay or that it's enough to just follow your dreams.

If kids say they want to do something like skateboarding, most people’s parents are like, “That doesn't make any money, so you can't do that.” But my parents were like, “That doesn't make any money, so you gotta find somewhere cheap to live. But that sounds sick. Go for it.” We didn't have much, so I think they were just stoked on me being interested in doing anything. I was also the baby, so they were just like, “Get the fuck out of the house, please.” But yeah, I tell everyone to just follow their dreams. I'm still figuring shit out all the time. I don't want to be a role model necessarily, but it's very sweet that people do. I still want to get better at skating. I want to get better at music. I still have goals and dreams yet to be achieved.