Sissy Strolls bring queer people of color together in WeHo

A group of gay black men smiling and drinking at a bar in WeHo

By Martine Thompson

April 25, 2024 3 AM PT

On Sunday nights in West Hollywood, the stretch of gay bars lining Santa Monica Boulevard look mighty different when a Sissy Stroll is underway. The monthly bar crawl, which includes the hot spots Revolver, Mickey’s and Heart, was created by dynamic trio the Sissy Squad. The mission? Curate a social hangout that prioritizes genuine connection among queer Black people, queer people of color and those who support them, while joyfully taking up space in WeHo’s notoriously white nightlife scene.

The Sissy Squad consists of Matthew Brinkley, a.k.a. Dr. Brinkley, a psychotherapist who focuses on relationship and queer life coaching; Neville, a.k.a. Aunt Jackie, an event producer and founder of Obtaining Mental Wellness Inc.; and David Brandyn, a writer and sex educator. In an effort to satisfy their appetite for stepping out on the town while at the same time addressing the lack of comfortable social spaces for queer people of color in West Hollywood, the group channeled their creativity and community-building skills into creating the change they wanted to see with support from partners House of Love Cocktails, Impulse Los Angeles and Obtaining Mental Wellness.

“When I first moved to L.A., I asked a friend of mine who grew up in L.A., ‘Where are the Black spaces where I can see myself?’” Brandyn says. “He said, ‘There are none. ... It’s been a long time since we’ve had a space. But what you do is, you gather all the Black people and you infiltrate the space that you want to be in’ and I never forgot that.”

members of the Sissy Stroll at a bar in WeHo

“What I’ve always loved about the Sissy Strolls was that it was a curated safe space for queer people of color and their allies. It’s not exclusive,” Neville says, noting that people of all different racial and ethnic backgrounds, sexualities and gender expressions have enjoyed themselves on a Sissy Stroll. “It shows that ‘sissy’ can come in any form. Come drink these free drinks and pop around with us and dress how you wanna dress and tonight, we all sissies. It’s just a fun word and I love that we have led this renaissance with the word sissy.”

“Now personally, I wasn’t really called a sissy as a kid, I was called the f-word,” laughs Brandyn. “Sissy, to me, spoke to the f-word in a lighter way. It spoke to the way that folks have treated us, the damage that folks have done to us because of who we are, and reclaiming it just feels really good.”

It’s a moment when people attending a Sissy Stroll show up at the meetup location — and it’s an absolute vibe when the group enters a bar as a unit. “Those clubs look so different when we’re there. And when we leave those places, you get to see this storm of people of color walking down Santa Monica,” Neville says. “It’s really impactful. It’s like, OK, the Sissy Stroll is here.”

For regular attendees like Roy Covington, a musician and Virginia native who relocated to Los Angeles a year ago, the feeling is exhilarating: “Once you make it into the bar, everyone is there and people are there to greet you and they’re so happy to see you and it just feels so good.” Covington credits the genuine warmth of the Sissy Squad, whether they’re hosting the Sissy Stroll, a game night or another local event, with helping him make organic friendships while building a foundation in a new city. “Any event that the three fellas host is a very warm, loving and just come-as-you-are kind of experience. It’s so great and they just want everyone to have a good time.”

The ritual of dressing for a Sissy Stroll is special for the three co-creators: thoughtfully applying glam, adorning oneself with feel-good accessories and being seen while each Sissy sparkles in their authenticity.

For Brinkley, serving a look is a mixture of feeling fabulous, important and powerful. “I feel like Sailor Moon when she transforms into herself to fight crime, or do whatever, that’s how I feel.” Brinkley’s aesthetic in a nutshell? “Something furry but sexy, tight — and I know my ass looks great.”

For Neville, who brings the maternal, auntie energy to the group, his fashion taste leans more modest. A statement hat with a big brim and in a variety of colors is a must. Flourishes like a rhinestone fringe or a leopard pattern peeking out underneath is to be expected, alongside a chunky heel or raised moon boot and an array of vibrant glasses and earrings.

“I’m more of the cool, rich auntie vibe. Like, you can go over to Auntie’s house and drink. You get to go to Auntie’s house and you might get to hit that blunt for the first time or if you’re not allowed to eat bacon at home, Auntie Jackie gon’ make sure to slip you a little piece of bacon,” Neville says. “During the Sissy Strolls, it’s like when Aunt Jackie puts on her good outfit to go find an uncle. Rich Auntie is stepping out and putting on her Sunday best, but in the gay way.”

Brandyn, on the other hand, enjoys rocking his signature combo of a masculine chain paired with a short mini skirt. Plus “an unconventional hat like a beret or cowboy hat,” an abundance of sparkles and rhinestones and a boot with a 5- or 6-inch heel. Something “tight on the top and loose on the bottom” is the motto.

Getting dressed for a Sissy Stroll can be an opportunity for playful experimentation when it comes to fashion, but it’s also a sacred form of inner child healing, explains Brandyn. “I dress for the little boy in me that really wanted to wear these clothes so badly but felt like he could not do it. That’s why my style is very late ’90s, early 2000s, ’cause that’s the age I grew up in,” he says. “When I’m with the Sissy Squad I know I can wear anything I want, I can behave any way I want, ethically of course. It gives us permission to truly just be whatever we want and that feels really good for us — and I’m assuming it feels that good for the folks who come on the stroll.”

For Ty White, 28, the Sissy Strolls have been an affirming space to make both personal and professional connections. “They cultivated a really nice space for people to network. I’ve met people who are hairstylists, some people do makeup, some people are producers for shows,” White says. A queer get-together with people who possess an understanding and a certain degree of cultural fluency from navigating the world as a fellow openly queer Black person has been a major plus for White.

“Even though places have the reputation of being occupied by a certain demographic and catering to a certain demographic even, it doesn’t have to be so lonely,” White says, referring to the prioritization of men who are “white, muscular, and under 130 pounds” in numerous gay spaces. “I encourage others to put themselves out there in any capacity for community-building because you never know how many people are having the same experience that you’re having,” he says. “I think the Sissy Stroll has done a great job of putting themselves out there … and pulling people in to create a community within a larger community and making people feel like they belong.”

Gay men smiling and hugging at a bar in WeHo

Beyond the Sissy Squad’s impact in Los Angeles, the group continues to leave its mark around the globe thanks to its show “Sissy That Psyche,” which streams worldwide on WOW Presents Plus. In the eight-episode series, the three hosts revisit and analyze “RuPaul’s Drag Race” meltdowns through a mental health lens — in fabulous outfits — and provide self-care tools viewers can apply in their day-to-day.

It’s not lost on the three Sissy Squad members that they are, as Neville puts it, navigating the world as “three chocolate men.” Colorism and the many other branches of racism and white supremacist culture are real and omnipresent. “It’s always kinda like, the extra stigma. We have a really cool way of representing three different points of view but looking like we’re together,” Neville says. “We are three chocolate men who play with androgyny, wear feminine clothes but still have this masculine edge to it and it’s really inspiring. People have literally come up to us and said thank you all for showing up this way.”

When you Google the word “sissy,” you’re sure to find a handful of definitions that list the word as a derogatory term for boys and men who are perceived as feminine, gay and existing outside patriarchal imaginings of acceptable masculinity. But as the Sissy Squad regularly affirms, a wealth of nuance and subversive power exists within the word.

“Basically, what they’re really saying is a person who has feminine qualities or who is femme-presenting [isn’t positive],” Brinkley says. “Actually that can be really great. That can be so amazing to have those qualities. Being soft can be very powerful and so I do think reclaiming it to make sense for us and the people who use it is really, really powerful. I hate the definition that’s in the dictionary [for the word sissy], but I’m so glad that we can look beyond that and create our own definition.”

Keep up with upcoming events hosted by the Sissy Squad on their Instagram @sissysquadla