Maddie McCuddy
First Place
University of Montana
$10,000 Scholarship and Hearst Medallion
Milo Kirby, 16, is “capital W Wasian,” she says, a phrase that refers to White-Asians.
First generation American, Kirby, was born in San Francisco’s Chinatown, but later moved to Marin County, a predominately white community in California. While living in Chinatown in an apartment with her entire extended family, above the bustling streets, she felt deeply rooted. But after moving to Marin County, she had to navigate public schools, new friends, independence and a place absent of her culture.
When Kirby was 13, she moved away from her parents, and back to the city where she was able to spend more time in Chinatown. A year later, she opened her own clothing store, selling her own Chinese streetwear clothing line, ‘MK Streetwear’, named after Milo Kirby Streetwear, with the support of her parents.
Although she wouldn't change how she grew up, in the first few years of her teenage experience, she’s worked on pulling back her Chinese cultural roots by establishing her own identity in Chinatown.
“I want to do as much as I can to make this community thrive—I’m dedicated to keeping Chinatown, Chinatown,” said Kirby.
Caption: Milo Kirby, 16, gets her picture taken by her friend, Abigal Li, after their teen pageant league represents the third annual Cultural Festival in San Francisco's Chinatown, in California on May 31, 2026. The festival continues each year to ensure that Chinese traditions are passed down to future generations.
Kirby, stands in line to participate in a ribbon cutting ceremony, celebrating the third annual cultural festival in San Francisco's Chinatown, in California on May 31, 2026. Kirby recently won the title of Miss Teen Chinatown 2026 in the 55th Teen League Pageant, the highest award in the league. The pageant's focus is on teen leadership and charity within Chinatown.
Kirby shops in a grocery store in San Francisco's Chinatown on May 31, 2026. Although she moved away from Chinatown at a young age, her mom has always worked here. "I got to stay deeply connected with Chinatown, thankfully. Even though I moved to a predominantly white area," said Kirby. After Kirby moved by herself back to San Francisco in the eighth grade, she eventually moved back to Marin County with her parents. Now, her and her mom, Celene, commute an hour to San Francisco from Marin County everyday for work.
Kara Lee (right), 17, the second Princess of Chinatown, records Kirby and her friends dancing to a Tik Tok in the streets of Chinatown in San Francisco, California on May 31, 2026. Kirby thinks that social media helped her feel better about her Chinese culture. "Whatever culture you are-- like on the flip side, Tik Tok shows something completely different. So I started getting more involved in my culture and I went back to it and like start dressing more Chinese."
Kirby's mom found eight copies of the local newspaper to pass around to family and friends, after Kirby was highlighted on her pageant win. "I'm going to frame it and put it on my wall," said Kirby.
Kirby walks her puppy, Hoshii, out of her own store 'Milo Kerby Streetwear', to go pick up her friends in San Francisco, California on June 2, 2026. Kirby moved away from Chinatown when she was four, to Fairfax in Marin County. "Safety in marin is so important, compared to china town," said Kirby. "But yes-- it divided me from my culture."
She decided to open her own clothing store in Chinatown because how deeply rooted her family was there and how thankful she was of the community. "We opened at a perfect time, because they opened a nightmarket after the pandemic," said Kirby. "We did really well our first year-- Now there's way less people because of the tariff's. No one wants to spend their money. Its hard for both busineses and customers. It's not enough to make a living"
Kirby and her mom, Celene, work on inventory at the shop in San Francisco's Chinatown, in California on June 1, 2026. Kirby claims she never really knew her white side growing up, even though her dad is white. "My dad's pretty involved with Chinese culture-- but we’re the furthest from a typical Chinese family," said Kirby. "I have the greatest mother ever, she’s so supportive and so is my father. But we’re so untraditional!”
Celene immigrated to America from China when she was 29, following her Great Aunt to San Francisco. She worked in restaurants up until her daughter had the idea to open MK Streetwear, and she started to help in the shop. "Everything was Milo's idea," says Celene. "She asked me to help her, but actually she took care of all of it. I think that's why she has so much pressure", said her mom. "She had her own mind really strong--she makes everything happen."
Kirby waits to be helped at Select Physical Therapy so she can get cleared to participate in cheer practice, after a month long concussion in Marin County, California on June 2, 2026. Kirby has been going to the doctors at least once a week since she was nine, and had to spend three years in and out of a wheelchair after being diagnosed with bertolotti syndrome and fibromyalgia. As a freshman in highschool, Kirby got a spinal fusion and has dealt with chronic pain, affecting her work and school life.
"I had to relearn how to walk and relearn how to do everything," said Kirby. "It's hard to be the pitied one in the family--I'm in chronic pain all the time. So it could be, oh, all of a sudden my, whole arm gives out or my whole leg gives out. They want me to leave the business and rest, but I'm too determined."
Kirby is driven by her self-driving Tesla to her club cheer practice in Tracy, California on June 1, 2026. She bought her car specifically because it could self-drive, because of her lingering health conditions. Before she got her liscense, she had become a tester for the self-driving car company, Waymo. "I was the number one rider for Waymo for so long," said Kirby.
Kirby's assistant principle, Ashley Saephan, met her privately after the school year had wrapped up so she could take her last state testing at Independence High School in San Francisco, California on June 2, 2026. After Kirby's concussion, she had a hard time keeping up in school. "Milo was willing to make this work," said Saephan. "So I was willing to meet her and make it work as well."
Kirby is triple enrolled in three different schools-- Independence high school, Galileo Acadamy for cheer, and City College of San Francisco for early college credits. "I'm going to take a gap year to expand the business," said Kerby. "I want to study business and maybe fashion design. I've always been doing 900 things at once."
Kirby and her boyfriend, Vincent Yip, 17, look at different raman dinner spots on google maps at Stinson Beach with Kirby's friend Mandy Yu, 15, in Marin County, California on June 2, 2026. It was Yu's first time being in Marin beacuse of her restriction to public transportation.
"I look up to Milo," said Yu. "She kinda treats me as her younger sister, and she drives me around-- we aren't blood, but everyone's connected in Chinatown."
Kirby and her boyfriend hang out on Stinson beach, Kirby's favorite beach in Marin County. She's grown to love the nature that Marin is filled with, compared to San Francisco. Kirby is glad she grew up in Marin, where crime wasn't as prevalent as it is in Chinatown, where she was born.
"The crime has gotten worse and worse. It's like no one feels safe to even leave their house--- I know a lot of people that go back to their home countries, like back to China," said Kirby. "That's why I'm so appreciative of being raised around here, it created my childhood for sure. I would never wish for anything else."
Kirby and her mom, Celene (left), learn to fold the traditional money origami, the lotus flower, at Chinatown's third annual cultural festival in San Francisco, California on May 31, 2026. After the pandemic, many businesses in Chinatown struggled with having the younger generation more involved with cultural traditions.

