She had already won the famed Miss Continental pageant, developed relationships with high-profile designers, and mothered several drag children — including season 14 star Kerri Colby. For Colby, her journey in the world of drag — and as a transgender woman — is stitched into her garments.
Beginning with her youth in Hawaii, Colby formed a lifelong relationship with clothes as a means of gender expression and freedom. And she had some unintentional helpers.
“The funny thing is how my parents would dress me,” Colby reflects. “In elementary school, I was already a blond kid in the middle of Hawaii. I had green eyes, pretty fair skin, and was femme-presenting. Then they’d put me in these little shorts that no other boy was wearing. And I was like, ‘So you really want me to just get more beat up, right?’ I felt like my parents unintentionally dressed me up very feminine, and they didn’t even realize it.”
Short shorts were just the beginning. As a child, she tried on different forms of feminine presentation, which allowed her to access new realms of creativity.
“The first gender-affirming clothes I ever put on were my sister’s negligee and bra,” she recalls. “From elementary to high school, I would come home and I would play in my sister’s makeup because she would have it in the bathroom. So it was easy for me to just grab a little liner, put some mascara on, light a candle, put on music. There was a radio inside our bathroom, and I would lip-synch in front of the mirror for hours — three hours, from 3 to 6 [a.m.] And my dad would be pounding on the door saying, ‘Get out, I have to shower!’”
Even today, Colby doesn’t believe her family understood what she was doing in the bathroom. “No one asked…ever,” she says with a laugh. “Maybe they noticed that I had black around my eye or little leftover remnants of makeup. But they never really pressed it. They’d just be annoyed that I’d be taking up the bathroom.”
Her teenage years also marked a major turning point in her sartorial self-discovery. “My first gender-affirming, ‘Oh, I’m trans and this is how I’m going to present myself,’ was in high school,” Colby says. “I was around 17 and dressing up for Halloween. A bunch of my friends rented a hotel in Waikiki. My best friend, Lindsay, who’s still my best friend to this day, fully let me be in drag. We all walked around Waikiki and I just felt like…‘I’m a girl.’ It was so empowering. I was finally seen but not gawked at. I was really awkward before I transitioned, but as soon as I started presenting [as] how I actually felt on the inside, a lot of people were like, ‘You just seem so much happier now…. It’s so nice to see you.’”
Over the years, Colby kept expressing herself through fashion and evolved her style as she gained more confidence and experience. In fact, every dress tells a story. Read on to hear about them.
Kristofer Reynolds Photography
Crowning Glory Colby triumphed in the 2012 Miss Continental pageant, which garnered her this crown. She recalls, “This is right when I won. When you win any big pageant, it is a job you’re taking, which is why I always think about it when I wanted to do Drag Race. Everyone thinks that the competition is the real hard part, but it’s actually doing the job after.”
Winning Miss Continental gave Colby a sense of responsibility that comes with the platform of the title. “Being able to represent what I felt I loved about Miss Continental was really important. I was traveling so much…. The Continental schedule was fierce. I sometimes had to do two or three different cities, different states even, in one weekend.”
The “First Incarnation in Drag” Colby was gifted this leather piece from one of her sons, the fashion designer August Getty; previously, it was hanging in his personal closet. Even though she first wore it for a recent photo shoot, the look is reminiscent of her “first incarnation in drag.” She explains, “I was the rock-and-roll girl, this platinum blond thing, walking in Hawaii. Not a lot of girls had the commitment to go blond-blond…and I was platinum. I was feeling my Gwen Stefani era, very ‘Hella Good’ [by No Doubt]. I am a kid of the 2000s, so I did love me some emo, Hot Topic. Give me a rubber band bracelet up to my elbows, please.”
Courtesy of MTV
Something Borrowed “When I first ran Miss Continental in 2005, that was the first gown that I ever wore,” Colby says. “And it’s actually my drag mother Cassandra Colby’s gown that she wore when she won Miss Universal Show Queen, which is a very big pageant based in Hawaii. It was a big bustle that she had, and I repurposed it as a cool little coat. I just love having sentimental drag pieces. That gown goes back so far — 15 years now.”
Courtesy of MTV
Hawaiian Warrior This drag veteran put a lot of thought behind how she would enter the Werk Room of RuPaul’s Drag Race for the very first time. “My drag is very everywhere, like a drag chameleon. So I thought, What story do I want to start to tell first?” she muses. “And it went back to who I am as a person, being Hawaiian. I wanted to take on the idea of a powerful warrior, mixing in the black skirt, which is actually more so of a man’s skirt. It’s called a malo, which men wear more often than women. It felt like a little touch that maybe only other queer Hawaiian people would understand and be like, ‘Oh, wow. She’s doing the masculine/feminine thing, but in a Sasha Colby way.’”
As for the tattoos, Colby met with a Hawaiian culture specialist, Kumu Mehana Hind, to ensure she was making the accurate references to her origins. “I had a really long talk with her, and she wanted to really know my reasoning behind why I chose to have tattoos for this look,” Colby says. “For me, it was just aesthetics, but then she told me why we tattoo as Polynesians. It’s a very sacred ritual act, usually to commemorate a big thing that happened in your life: a big death or a big birth or a big transformation. When she said transformation, I realized that’s why I innately went to it, because it’s showing my transness as well. Even though I didn’t realize it at first, that was also a really powerful statement that I got to make.”
First Impression Colby’s first runway look on RuPaul’s Drag Race was a 10-year-old gown made by a New York City-based designer named Gustavo Bustos; she previously wore it the year she won Miss Continental. “He would do all the Miss Venezuela pageants back in the ’80s and ’90s, and he started doing a lot of drag, a lot of trans-drag pageants, which is why we all fell in love with him,” she says. “He’s a legend in the drag industry, so I really wanted to make a statement that night.”
The Next Chapter
Despite her already sizable reputation, Colby never underestimated the Drag Race experience as she went into filming season 15. “Let’s be real, Drag Race is the hugest competition in drag culture,” Colby points out. “I think of it as a televised pageant, so that’s why it was so easy to see myself competing. Going there, I’ve had a lot of life happen to me. I was also ready to just be present in not just the competition but understanding that it is a show as well.... A lot of people see me as standoffish and maybe intimidating when they see me on stage, but everyone that meets me is like, ‘Oh, but she’s so sweet and goofy.’”
Could Colby soon wear a Drag Race crown with a story of its own? Considering the possibility, she becomes a little emotional. “To be quite honest, I just wanted my foot in the door,” she confesses. “‘Just get me on TV, please, and I promise you I’ll take whatever I get.’ I’ve just been working so hard and never thought that anybody was watching or even noticed it. The amount of love that I’ve gotten has made me feel like my 20 years of work really meant something, that people are really watching.
“My goal with Drag Race is to follow in the footsteps of all the successful Drag Race sisters that I’ve seen become more than their wildest dreams. Being able to seize opportunities. This is what Drag Race is about. Even the non-winners are such winners. It’s insane what you can do with just the opportunity. And I definitely go into this not just wanting to win, but just being like, ‘Man, if I could just get somebody to see me, then it’s on.’ That’s what I feel like. My opportunities are so much bigger now, and my dreams just got bigger.”
This article is part of the Out March/April issue, out on newsstands April 4. Support queer media and subscribe -- or download the issue through Amazon, Kindle, Nook, or Apple News.