'Everyone Deserves Good Cake:' Meet the Trans Woman Whose Chicago Bakery is Open For All

Walking into Jennivee’s Bakery in Chicago's LGBTQ-friendly Boystown neighborhood feels like being transported to a quaint, French boulangerie.

With its whimsical, gold-rimmed seating, vintage picture frames over exposed brick, beaded chandeliers and a colorful chalkboard menu, the bakery offers a comfortable, vintage feel. And, of course, its drool-inducing pastel cakes, cupcakes and other treats line the counters and front window, beckoning anyone with a sweet tooth inside.

Jennivee’s is a cozy, chic place, which is exactly what its owner, Jenne Vailoces, was hoping to achieve. Vailoces, who identifies as transgender, opened her bakery with the goal of creating a welcoming space for the queer community and allies alike.

Anyone is welcome at Jennivee’s, regardless of their identity, Vailoces emphasizes. After all, "everybody deserves to have good cake," she says.

Photography: Kohl Murdock

Vailoces immigrated to America from the Philippines almost 10 years ago. She’s a physical therapist by trade, but baking has always been her passion. She started at 6 years old helping her mother in the kitchen, and now, at 34, her longtime dream of running a bakery has at last come true. Jennivee’s has only been open a few months, but business is already booming.

“I’m so thankful that it’s doing really well,” Vailoces says, well-aware of the high rate at which food-based businesses fail. She's showing her gratitude by doing what she can to help others in the community, especially transgender youth.

Boystown, where the bakery lives, has become a haven for homeless LGBTQ youth who come to the neighborhood in search of a safe, accepting environment. At any given time, blocks away from the bakery, homeless queer youth could be out looking for places to sleep and eat.

Vailoces is working to hire new employees through TransWorks, an organization that prepares transgender youth for the workplace. She hopes to help other transgender people circumvent the violence, homelessness, depression and high suicide rates that too often afflict the community. The message she hopes to send with her success: “There is hope, and you can still be happy and fulfilled. You don’t have to live a life of hopelessness and darkness.”

Vailoces’ best friend, Dakota, died by suicide a few years ago. She opened Jennivee’s in part as a way to honor his memory. Dakota, a gay man, left home at 17 after his family wouldn’t accept his sexuality. While he was able to build a life for himself, Vailoces says his emotional scars never healed. Dakota always encouraged her to pursue her bakery dreams, so she named Jennivee’s after the nickname he called her. His framed photograph hangs behind the counter, watching over Vailoces while she works.

Photography: Kohl Murdock

Raised Catholic and still a person of faith, Vailoces also felt stirred to open the bakery after hearing stories of Christian-owned bakeries refusing to serve LGBTQ couples. “It saddens me when I hear stories of people using religion as a justification to discriminate and to exclude people like myself," she says.

Vailoces and her family knew she was transgender very early in her life. “My mom said I was different even when I was inside her womb,” Vailoces says, adding that she's been lucky to have such strong familial support. She says Dakota once asked her what she’d want if she had the chance to be born again. “I said I would still choose to be trans because a lot of the experiences I’ve lived through in my life, although they’ve been difficult and challenging, I wouldn’t have had it any other way.”

Jennivee’s is quickly becoming a neighborhood staple, not only because it's an inclusive place, especially for transgender people, but because of Vailoces' tasty cakes. Among her bestsellers are the Mango Crème Cake and the Purple Velvet. She serves a few authentic Filipino desserts, though she's especially interested in classic American ones. Many bakeries, Vailoces says, focus on European styles, but she is most excited by American cakes like the Lady Baltimore, the Mississippi Mud and the Southern Style Coconut—"Cakes that grandmothers would make and bring to church meetings," she says.

Right now, Vailoces is looking forward to Chicago’s Pride Parade in June. Everything will be rainbow-colored, she says, and her friends, dressed in drag, will be dancing on the patio, passing out cupcakes to passersby.

"Hopefully this bakery will be a mainstay for the LGBTQ community,” Vailoces says. “I feel like Chicago needs a bakery that the LGBTQ community can proudly call their own."