How I Shop: Author and Activist Jacob Tobia

The creative, who recently published their debut memoir "Sissy: A Coming-of-Gender Story," shares their earliest shopping memories and why they prefer to shop thrift and vintage over traditional, gendered retail environments.
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 Jacob Tobia attends The Human Rights Campaign 2019 Los Angeles Gala Dinner at JW Marriott Los Angeles at L.A. LIVE on March 30, 2019 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for The Human Rights Campaign )

 Jacob Tobia attends The Human Rights Campaign 2019 Los Angeles Gala Dinner at JW Marriott Los Angeles at L.A. LIVE on March 30, 2019 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for The Human Rights Campaign )

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."

Style is one of the many ways writer and queer activist Jacob Tobia has discovered their femininity. According to the Los Angeles-based creative, clothing and accessories have always played a major part in understanding their gender identity — a deeply personal topic that is now the subject of their debut memoir tiled "Sissy: A Coming-of-Gender Story", which released in March 2019.

"The reason I wrote 'Sissy' was because I wanted to tell how I came to understand who I am, what influenced and helped me get to a place of self-actualization and empowerment as a gender nonconforming person in a world that makes that really hard," explains Tobia over the phone with Fashionista. At 27 years old, the writer and performer also uses social media to share ruminations on their outfit choices, and the ways in which they are often subject to street harassment for expressing themselves through fashion.

For example, for a recent appearance on "The Daily Show," Tobia wore a red dress by Prabal Gurung, which was once modeled by Ashley Graham on the runway. Sharing an image of the dress on Instagram, they wrote, "It is radical to adorn trans bodies. It is radical to support trans artists and empower us to feel beautiful. It is radical to celebrate gender nonconforming aesthetics, to redeem trans beauty in a world that has so often deemed us ugly."

Here, Tobia fills us in on their earliest shopping memories and why they prefer to shop thrift and vintage over traditional, gendered retail environments.

Jacob Tobia attends Teen Vogue's Young Hollywood Party, Presented By Snap at Los Angeles Theatre on February 15, 2019 in Los Angeles, California. (Photo by Gregg DeGuire/Getty Images for Teen Vogue )

Jacob Tobia attends Teen Vogue's Young Hollywood Party, Presented By Snap at Los Angeles Theatre on February 15, 2019 in Los Angeles, California. (Photo by Gregg DeGuire/Getty Images for Teen Vogue )

"One of my earliest shopping memories were the sad excursions I took to Kohl's growing up. It wasn't because Kohl's was sad, it was because I was confined to the most boring part of the store — the men's clothing section, which promoted a templated, boring version of masculinity. Men weren't allowed to adorn their bodies with things that were interesting then.

If you were assigned male at birth, you had to wear garments of a specific shape. Back then, I couldn't find pants that fit me. I couldn't find anything that was interesting from a visual perspective. I couldn't find anything that was colorful. There was no sparkle. No textured fabric. The only way I could figure out how to wear color was with buttoned-up polyester shirts from around 1997 through 2003. You know, like those Guy Fieri shirts? That was my shit in fifth grade because it was the only way I could wear any color. That was the queerest I could let myself be.

I could not cross over to the women's section when I was on supervised shopping trips. And even when I was on an unsupervised shopping trip, I was still really scared to be properly gay. I couldn't even buy a shirt that felt gay. I just had to be Guy Fieri and that was my fashion sense for two or three years until my friend was like, 'I'm taking you shopping at American Eagle,' and then from there, I went through it more in a preppy direction.

I think a lot of my fashion sense now comes from my grandma on my mom's side, who was my style icon growing up. She was this cute lady wearing shoulder pads and windbreakers well into the 2000s. She wore a lot of bright, rhinestone clip-ons that were chunky, distinctive and fabulous. I got my penchant for patterns, florals, bold geometric prints, shoulder pads, bright-colored blazers and chunky jewelry all from my grandma.

There's a lot of days now where I give myself permission to be lazy and fly under the radar because being trans feminine in this world is exhausting since the attention is constant. The moment you put on lipstick, everyone's staring at you forever. 

On the days when I try to dress interestingly, it's like 1980s kinky grandma chic. For example, maybe I'll wear a bright geometric blazer with a little leather collar and some big, chunky clip-on earrings. That's my default. And that aesthetic serves me well because you can find it in any Goodwill across the country. Or I'll find an entire collection of unique earrings at an estate sale in a plastic bag for 10 bucks. To find cool clip-ons, either you go to a flea market somewhere really tiny or somewhere rural, or go to an estate sale after a really lovely grandma has had moved on to the next phase of life.

I don't get why people are so obsessed with having an aesthetic that always feels very modern. I don't like looking modern. Modernity bores me. I like looking tacky and old. It's a way of staying grounded and honoring my heritage and the women who I adored in my childhood. I don't want to seem like some Manhattan socialite. That doesn't feel as fun to me as looking like the cool grandma from church. I don't know when we lost the idea that fashion could be play.

Except for The Phluid Project, I find that most retail environments are profoundly gendered in terms of the fit of their clothing, as well as the actual layout of the store. I'm just so bored of that. It's really hard for me to have fun in a high-fashion store. I just want to put my dollars behind spaces where I feel included.

Also, I'm a socialist little lady and I don't like the way capitalism controls fashion. Why are fashion months necessary? Fashion should be about community and inclusion where everyone feels welcome and doesn’t have to spend a lot of money in order to look distinctive. Fashion shouldn't be about how much money you have or what label you're wearing. It's an oppressive, classist way for fashion to function. So, I'm boycotting mainstream retail until they figure out a way to make fashion less shitty for everybody.

Jacob Tobia attends the 30th Annual GLAAD Media Awards at The Beverly Hilton Hotel on March 28, 2019 in Beverly Hills, California. (Photo by Frazer Harrison/Getty Images)

Jacob Tobia attends the 30th Annual GLAAD Media Awards at The Beverly Hilton Hotel on March 28, 2019 in Beverly Hills, California. (Photo by Frazer Harrison/Getty Images)

To me, shopping vintage and thrift is the revolution. I pretty much exclusively shop vintage and thrift. The only time I go shopping in retail stores is when I need pants because finding pants vintage or thrift can be tough. And underwear and socks I generally buy new. Other than that, most of my distinctive pieces are vintage or thrift or found or passed down to me.

The options are just so limitless. With thrifting, you might have that beautiful moment of discovery when you find something that is so gorgeous, but has been overlooked or maybe you happened to pick it up at the exact right time. I got a beautiful Cinderella princess gown at a Goodwill in Silver Lake for $7.99. That moment of discovery is so much more exciting to me than finding a gown at an expensive designer store.

Today, I mostly shop when I'm hanging out with friends in other cities, visiting my hometown in North Carolina or when I'm traveling for a speaking gig. My favorite thrifting and vintage is when you get outside of major metropolitan areas. Maybe I'm going to spend $100 on 10 pieces and I'll mail them all back to myself in L.A. and I'm going to have all the things I want for spring.

When shopping for vintage stuff, the sizing is the hardest part, so I have to try on a lot of things to find stuff that actually fits me properly and is big enough to accommodate all that I got. But, to me, it's worth it because when you find something that really does, and I'm like, 'Oh my gosh, this is incredible.'

There's also a sense of 're-homing' a piece: Maybe someone else no longer found value in this thing but I'm going to pick it up and give it to the new life. There's something redemptive about that. There's something almost spiritual about it."

This interview has been edited and condensed for clarity.

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