How I Shop: Sasheer Zamata

The "Woke" star shares how she plans her standup 'fits, where she finds the best vintage and when she's outfit-twinned with best friend Nicole Byer.

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

Sasheer Zamata literally rolls — as in, roller skates — into the season two premiere of "Woke." Or rather, her character Ayana, an editor at a San Fransisco alt-weekly, does. Anyone who follows Zamata's Instagram (and listens to her podcast, "Best Friends," co-hosted with BFF Nicole Byer) knows that the actor, comedian and writer picked up and immediately excelled in the zippy sport over pandemic.

"It was actually the writers' idea," she says, thinking that the show's scribes were probably also stalking her IG. "I like that they were able to think of fun ways to get me into the character."

The second season of the Hulu comedy, inspired by the life and work of "The K Chronicles" comic Keith Knight, finds the core four in new stages of life and career. Cartoonist and newfound activist Keef (Lamorne Morris), for one, navigates his widening platform, growing pressures from followers and the monetization of social justice causes. Ayana finds herself in an unfamiliar place, too — first facing the realities of San Francisco real estate, then being threatened in her role as Keef's social justice compass, thanks to... mmm, new developments.

"I'm excited that we get to see Ayana unravel a little bit," she says. "I feel like she was more of the guru or the 'woke' guiding light in the first season. In the second season, we see more of her as a full person, who also has insecurities and worries and stressors, and isn't so unfazed by things. That's exciting for me to explore, because that's real."

The "Saturday Night Live" alum is currently juggling co-starring on "Woke" and the ABC sitcom "Home Economics," plus prepping to shoot her upcoming standup show in June. As for her outfit for the latter, "I'm just bouncing with ideas right now, because it is important," she says. "It's gonna be cemented in time. So I want it to be comfortable, but also something I would like to see [myself in] years from now."

Because how you look and feel on stage is integral to the performance (not to mention part of jokes workshopping process), Zamata dons prospective outfits while rehearsing bits and routines. "You never know what you're gonna do and I don't want to have something on that's going to limit me," she says. "I want feel free to be able to move around and be the most me I could be."

Back in 2017, Zamata told InStyle about how women standups deal with unspoken rules in what to wear on-stage. Is this too sexy, thereby distracting from your jokes? Or are you looking like you tried too hard? Five years later, she's noticed an evolution in style and a breaking of boundaries and expectations — both from audiences and comics.

"I do feel like there's now a lot less thought as far as having to cover up or having to look a certain way on stage. Maybe it's because there's just more diversity in the people doing standup and more people being like, 'Now, this is me, and I'm gonna showcase myself the way I want to be showcased,'" says Zamata. "I like seeing people choose their style the way they want to. Because standup is very personal. You're representing yourself, so if you feel the most comfortable in your underwear, go for it."

Ahead, Zamata shares what she likes to wear for her own live shows, when she's outfit-twinned with Byer (spoiler: a lot) and how her bestie influences her expressive style.

"I guess my style is... comfy-chic? I like jumpsuits. I like overalls. I like one-pieces that make it very easy for me — or matching sets. People would probably say 'earthy,' but also I do like bright colors. But I guess the earth provides bright colors, so maybe that would still apply. It's earthy in a way that's also exciting.

"Before the pandemic, but especially during the pandemic, I've definitely been on the hunt for things that look good, but are also very comfortable — something I could probably lounge around in at home, but also leave my house in and still look good. One of my favorite sweatsuits is from Farm Rio. It doesn't look like a sweatsuit at all, but it is. Every time people see it they're like, 'Oh my god, it's like so cute!' And I'm like, 'Yeah. It's also really comfortable. I could sleep in this.' That's the perfect combination of things for me.

"I feel like I keep stumbling on the brand's stuff and being like, 'Oh, where's this from? Oh, Farm Rio!' I just love it so much. I like how it uses nature elements, like the flora and fauna, in patterns, because I love involving nature in my life, in my home, in my office and in my clothing.

"I curate my clothes in a way to show my creativity. I like being able to use clothes as an example of my artistry. My clothing shows my sensibilities — it goes in and out of being feminine or masculine; neutral or crazy patterns. It really just depends on my mood. But I like being able to play with different styles and color schemes, and use that to show my personality.

"I still like to have the elevated look [when I'm performing]. Sometimes I'll go on stage with the matching sweatsuit I just described, looking like I tried to put myself together for a show. Because there's still a show. People still paid money to come see me perform. I don't like to show up in like a T-shirt and flip-flops. I want to like look nice in a way that I think I look nice. But I also don't want to want to, like, have a gown. Somewhere in between gown and sweats is where I land. Also, elevating my look — from me being on the couch — helps me mentally because I don't want to feel too comfortable. I want to be in performance mode. I feel like the way I dress helps me get into performance mode.

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"My friend Bry Crasch has a line called Crasch Clothes. I wear it on social media and in my life to help support him. Nicole saw me wear [one of his matched sets] and was like, 'Oh my god, I love that. I want it.' So she got the exact same one. We had a live-taping of our 'Best Friends' podcast at the Largo, and I was like, 'What should we wear? Oh, wait, should we wear our matching outfits?!' She was like, 'Oh my god, I love the idea.' Not only are we matching, but they're wild outfits — like swoop-y swirls and crazy patterns. Your eyes are really drawn to us if we're wearing it individually, but together, it's a lot. I think that was a crowd-pleaser! And now it's like, 'Well, do we have to do that every time?' We set the bar so high for ourselves.

"It was also funny because we have many matching outfits. We have rhinestone jeans. We have this shiny dress that we bought off Instagram. Sometimes it happens on accident — there was one time I met up with her, and I put on this black and white polka dot romper, and she was wearing a black and white polka dot shirt and polka dot jeans. I was like, 'How is this possible?!' We just show up and be like, 'Whoa!' Also, she was at the premiere party for 'Grand Crew' in this orange fuzzy dress, and I walked in with a yellow fuzzy shirt that was the exact same material. We're like, 'How, how does this keep happening?' We're just on the same wavelength.

"It's funny. We're both so serious about shopping — like, we love shopping so much that we don't actually shop together. We split up immediately, as soon as we get into a store, and then just scour the racks because we're on a mission. We're on a hunt. We're literally hunting. She'll go to one end of the store and I'll go to the other, and if we find stuff, we might hold it up in the air and be like, 'Do you want this?,' and be like, 'Yeah!' and put it in our carts. We might meet in the middle and start walking down the aisle together and chatting, but for most of the time, we're not talking. We're on the move, trying to find all the goodies and the treasures in said store.

"Shopping is the activity I do when I go on the road and do standup in different cities because that's a great way to see the city and what people's tastes are. Sometimes the best thrift stores are in cities that are not New York and L.A. — actually, most of the time, because the prices aren't crazy high and it hasn't been picked over because there are a million hipsters trying to get the same thing. I go in and I take all their goodies.

"When Nicole and I were doing improv in Edmonton, Canada, I got these amazing acid-wash jeans from Divine Decadence. [Note: it's now closed. Sad.] That's how good it was: I remembered it. It was all this cool '80s stuff, and Nicole picked out these jeans and an overall set that I have still. It's purple and green and blue, and has all these cool patterns on it.

"It's helpful for us to shop together because we'll pick up stuff that we think the other person will look good in, but that the other person may not necessarily have thought to pick up. Like, she'll pick up things with a wild pattern, and I'm like, 'Really? You think I can pull that off?' She's like, 'Yes!' Or I'll pick up something that's a little sexy and be like, 'Try this!.' and she's like, 'I don't know.' I feel like we've helped each other push the bounds of our fashion because we see each other the most — like, I'm looking at her all the time, so I'm like, 'I think you will look good in this,' and vice versa.

"I was averse to the patterns at first, because I do think I had more of a solid, dark-toned wardrobe when we met. Then, the more things that she was handing to me in stores, the more I was like, 'I guess I do like bright colors.'"

This interview has been edited and condensed for clarity.

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