Subjective: Bailey Stewart

In this ‘Subjective’ interview we chat with Bailey Stewart, a Portland based artist and designer.

Hey Bailey! Thanks for being down for an interview. I know you grew up outside Chicago until you were around 18. Tell me about that early part of your life?

What’s up Alex, I grew up in Oak Park, IL. I was pretty artsy and loved to climb our roofs and all the neighborhood trees. We lived on this block full of kids and we’d play till dark, that was really cool! 

Did you find that artsiness was encouraged by anyone?

Shout out to my Gram! My grandma was this big personality who originally wanted to be called The Great Matriarch Teller of Talles (GMTT), but we settled on Gram. She was super messy and always had water colors, craft paper and snacks strewn about her house. I would go over and we would just go to town, painting, using gel pens, storytelling and really having no end goal but creating. She really shaped me. 

From there on out my parents were really supportive and let me have an art table so I would stop spilling india ink, acrylic paint and hot glue on the kitchen table, ha. My parents always sat through my impromptu dance performances in the living room and entertained my ideas. Looking back at it now, I realize how grateful I am for all of their support. 

Photos by Mara Lei.

For sure, it’s important. I know after high school you moved away to Colorado for college at Western State. What was that like?

Woah, that was life changing. After growing up in the midwest I wanted to be around mountains so bad, so I googled ‘cheapest school in Colorado’ and found Western, haha. Gunnison, CO is this rural blue-collar, high altitude desert and it has my heart. I really grew into myself there. I learned how to dirt bag and live out of your car for cheaper climbing trips and really show up for each other. 

Sick. I haven’t spent a ton of time, but in my few short times passing through it’s always been beautiful. I believe Colorado is also where you first got into snowboarding and skating, yeah?

Hahah yeah, I ended up crying my way down the mountain during the first season or two but damn do you learn quick when you want to keep up! I found my crew and really fell in love with the flow I found in snowboarding and how sick it is to be in the mountains. 

Then one year my roommate was a big skater and I’d go to the park with him. He convinced me to get a skateboard and slowly I started learning how to pump in the bowl and push around. I was super nervous and it wasn't until a few years later I really started to love it and try new things.

The skatepark was mostly dudes so I drew up some art and made a post on Instagram for Fem Skate Night. A bunch of girls showed up and we had this sick summer crew! Then it really became an all inclusive group of people and it was magical. It was a small town so there was only one park, I’d skate over from my house and always find friends there. My homie started an initiative called Mental Madness and we’d have meet ups at the skatepark to spread mental health resources, create community, and just really show up for each other. It was beautiful. 

Love that. Building community right off rip. And then you move to Portland at some point, tell me about the move?

Eeee the move was tricky! I went from being a big fish in a small pond to the total opposite. Honestly, I really struggled with the transition. It wasn't until recently I started to fall in love with Portland. Surfing, skating, snowboarding, so many social justice initiatives, sick art and finding some inner peace really seems to be the secret sauce. Working as a coach and illustrator for Skate Like A Girl helped me find a sense of community early on. 

Moving here, I really learned how to hustle. I thought I would get here and land a design position easy… but haha that was not the case. I would make these little care packages of my art, stickers, and zines and drop them off at design studios. I got some really cool opportunities from that and learned that rejection is a big part of life, especially in the art and everytime you go skate. Now, I’m really trying to lean into my own style and create things I love while also freelancing. 

I feel that, you gotta put yourself out there, but it’s not easy. Let’s talk a bit about your work. You had mainly brought up physical art growing up but I know you also do digital art, and I know that’s now become a major medium for you.

Mhm, my friends own this bagel shop in Crested Butte, CO (go eat at Butte Bagels!!!) and they wanted new shirts. So I thought yeah, how do I take a doodle to a printable layered design. So I dove into all things Adobe Illustrator, Procreate and how to make things for print. I asked hella questions, cold emailed like the whole world and really put a lot of time into learning the digital side and little 2D animation. 

How do those two modes digital and physical feed each other for you?

Painting, doodling, ceramics and screen printing will always feed my soul in a more holistic way, like I need to do those things. Graphic design and illustration are a great way for me to connect with people on a larger scale and work with really cool clients. It’s amazing to work with a client to bring their logo design or brand vision to life. I really want to be able to represent communities, small business and movements accurately through passionate and inclusive design. 

I like that you’re leaning into both. You mentioned zines, let's talk about that. Prickly Pear is your submission-based zine project with your best friend Nanni. What’s the story with that?

That’s our babyyyy. It started when a friend really crossed a line with me. He didnt ask for consent and it kinda fucked me up. I felt like I didn't know how to express those feelings in our society and I realized how many others felt the same. So we put out a call on instagram for people to share their stories. Stories of abuse, of love, shame and navigating the wild world of human intimacy. We really need to be having conversations. 

AND WE WERE BLOWN AWAY. So many poems, doodles, questions and essays flooded in and I learned how to self publish. What we thought would be a small zine printed out at the library turned into a full fledged publication. We ran a pre-sale to pay for the printing costs because we wanted it to look sleek and to honor people's experiences. Now we are currently + slowly chipping away at our third issue. Can’t wait for yall to read it. 

Photos by Mara Lei.

I have issue 2 sitting right here next to me, and it’s dope. Looking forward to the next one. Let’s go over some of your favorite projects over the years. Give me a few of your favorite things you’ve made or been a part of making?

Making the specialized Skate Zodiac Signs for Skate Like A Girls, WOF 12 is totally at the top! I’d love to expand this project and put them onto decks and merch.

Spitfire actually did a limited run of them on wheels, I cried haha. Maybe they will make more…

I made these Always Angsty Bandanas that I’m in love with.

Prickly Pear.

A mural for Airblaster HQ.

And so much more! I designed and illustrated a big sign for the skate park in Crested Butte, CO that highlights mental health resources in the community and how to show up for yourself and each other. 

So many sick projects. What keeps you making things, especially when life gets overwhelming?

Honestly, most times I don’t. When I’m overwhelmed I need to move my body, skate, dance or talk to friends. Then when the overwhelmed feeling leaves I can sit down and process everything on paper or through paint. Then it becomes a beautiful reflection process. 

Sounds like a pro tip right there; go move your body when life is hard. I love it. If you had no deadlines, no pressure, and total freedom what’s the first project you would be making?

Big and fluffy! I’d make a big community sculptural piece and maybe everyone could bring something cute to put on it. I’m thinking neon paint, found materials and we’d all be out there eating snacks working on this giant project. I’d love to paint more murals too.

Sounds nice. Anything we should be keeping an eye out for in the near future?

Airblaster drop this winter!!!!!!! Airblaster is a sweet Portland brand that makes snowboard outerwear and tighhtttt lifestyle clothes. You can definitely skate in them! They asked me to draw two patterns for this winter's collection and I can’t wait to see people wearing my illustrations. It’s the coolest thing that's happened to date! Also, I started making pottery again. So keep your eye on my IG for some custom Always Angsty mugs, sculptures, bowls and all things rad. 

Alright, well I could ask questions all day, but any final words of wisdom? Advice? Shout outs?

Be your own biggest hype man. You really gotta dive deep and be kinda delusional about your dreams. Make them big and chip away at them little by little. It doesn't have to be perfect to put it out. Call your homies, show up, trust your gut, call out abusers and stay angsty! Hit me up for projects :) 

Thanks so much to AB, this interview really helped me out of an art rut and inspired me to skate more. I love what your doing, keep it up <3

Hell yeah, so glad to hear it. Thanks again!

You can keep up with Bailey on IG and check out all of her work at www.alwaysangsty.com