Rocking out to vintage textiles with Kylee Kienitz and Lou Lou Rosenthal
Rocking out to vintage textiles with Kylee Kienitz and Lou Lou Rosenthal
Co-founders of Heads Or Tails Collective
There are numerous origin stories of Heads Or Tails Collective (H.O.T., for short), a vintage boutique and eclectic communal space perched on the second floor of an herbaceous-looking retail loft. It just depends on how far back you want to go.
One version begins with a bartender and singer-drummer crossing paths in Oakland’s music and restaurant scene and discovering a shared ambition in vintage and retail. Another is the tale of four acquaintances - a photographer, screen-printer, and two thrifting enthusiasts - opening a multipurpose studio in the storage unit of a Japanese fried chicken joint (where they soon acquire the skills of camouflaging oil, syrup, and barbecue sauce on carpet).
As the three of us sip tea at the brewhouse across the street from their shop, Kylee and Lou Lou - decked in 80's-style floral dresses, sneakers, and block heels - share how their personal journeys led them to a shared one.
Kylee, originally from Wisconsin, fell in love with fashion and thrifting at a young age - scavenging flea markets with her mom and grandma. While Kylee’s town and extended community didn’t quite understand the concept of buying and wearing second-hand clothing, she relished in treasure-hunting for uncommon pieces over trendy attire. First as a financial necessity and then for pure fun, teenage Kylee built a vintage collection and passion that eventually attracted her to the curious streets of the Bay Area. When asked how she acclimated to the neighborhood when she first moved in 2018, Kylee smiled and recalled that “in just my first weekend here, I visited a street fair and very quickly found community.” This was home. And it was easy.
“In just my first weekend here, I visited a street fair and very quickly found community.” - Kylee Kienitz
In a similar fashion, Lou Lou grew up up-cycling clothing and styling pieces from her parent’s closet and nearby thrift stores. Her mom, a costume designer, often brought garments home as well. Lou Lou also grew up in a musical family, and her friend circle consisted of a group of musicians, artists, antique collectors, and other creatives. She even shared that “music is responsible for every good thing in my life,” including the dawn of Heads Or Tails. Like her co-owner, Lou Lou had over the years grown a large selection of vintage finds.
So, when did it all come together? The two’s lives intersected through mutual friends during evenings spent at The Hatch, a beloved bar in Downtown Oakland. While they didn’t realize the opportunity to do business together until later down the road, their respective independent projects required physical space and talk of a collaboration surfaced. On the one hand, Lou Lou envisioned a future where her old-lady self manned a shop of her own, perhaps from a rocking chair power-positioned behind a tattered cash register and with a beverage or two in hand. On the other hand, Kylee moved across the country to pursue a career in vintage. Realizing they could together turn their individual dreams into reality, Heads Or Tails Collective was born in 2020.
Originally located in Downtown Oakland, California, the shop has since moved to 4125 Piedmont Ave #13 (As of Jul 11, 2024, H.O.T. is at 4188 Piedmont Ave!). Named after its variety of apparel offerings (from one’s head to tail) and also the whimsical element of chance, the boutique has become much more than a place that sells things. Every third Saturday, H.O.T. co-hosts a pop-up market with their neighbors The Sunshine Prophecy, transforming their common outdoor spaces into a lively dance party and bazaar. They also participate in many community events, including the annual Mosswood Meltdown, a wild celebration of counterculture and punk. Furthermore, they have a track record in hosting makers in their space. Currently in the studio is Karly Pearson (@penny_sierra), a sustainable artist apparel brand that custom-makes everything from funky bell-bottoms to dreamy blouses, and much more. Lou Lou and Kylee are also integral to the fabric of the Bay Area vintage community, and do a ton to promote their fellow small-businesses (check out their collaboration on the Oakland Vintage Shopping Guide here).
As we finish up our beverages and head over to their storefront to open, I prod the business duo on their guiding philosophies - for life and work. How did they navigate the challenges of starting a retail business in the thick of the recent COVID-19 pandemic? What has been critical to actualizing their visions?
The short answer: community. In Lou Lou’s words, if one is looking to start something (anything), “try not to do it alone. Or, if you are doing it alone, build or find a community because a movement can’t survive as a single person.”
“...try not to do it alone. Or, if you are doing it alone, build or find a community because a movement can’t survive as a single person.” - Lou Lou Rosenthal
From scouting their first physical location to their second, applying for a business license, forming an LLC, and designing their logo, Kylee and Lou Lou leaned on their community of former employers, friends, and family every step of the way - on top of trial and error a plenty. And, just as they have been inspired by the creativity, kindness, and resourcefulness of others, many patrons have gone out of their way to let the co-owners know that they’ve created something truly inspirational.
So, what’s next for Heads Or Tails Collective?
Lou Lou: “just rolling with it.”
It is apparent that H.O.T. 's community is rich with personality and love, and these two powerhouses are having the best time bringing together kindred spirits to make clothes, share art, laugh, and rock out. For the shop’s future, they would love to feature more makers and artists, host more on and off-site events, and maybe - one day - open up a second location.
Kylee and Lou Lou, your community awaits your next move and the chances look good.
Check out Heads Or Tails Collective next time you are in Oakland, California. Happy community building!