While in many cases, it’s one esteemed restaurant or another that initially attracts visitors to town, and yet, the shops they go on to frequent afterwards—or on the way—also play an important role in fostering that unique downtown atmosphere people love so much.
But now, two retail stores—Jackie ’O and East Kennedy—have announced they will be saying goodbye to their storefronts in the coming weeks.
Though both boutiques will carry on via their e-commerce presence, the goodbye is bittersweet. Because for each, this was more than simply a place of business.
Over the years, each of these shops helped to create a sense of belonging amongst their customers—and for the town as a whole.
Shortly after graduating from Chico State, Jaclyn Blackwell found herself working at a retail location on the corner of North Santa Cruz Avenue and Elm Street at a boutique known as Criv.
She worked there for a few months before taking over the space and starting her own boutique, with a name referencing hers.
Blackwell says the Jackie ‘O origin story involved a bit of fate, since she had mentioned the idea of owning her own store one day—and then the chance suddenly dropped into her lap.
“I always had an eye for fashion, so it was a perfect fit for my career,” she said, reflecting on how her employer presented her with the opportunity. She held an official launch in August 2018.
Becoming a business owner was a big step for Blackwell, as it was the first store she ever owned.
She’d learned some basics from the prior owner, such as how to purchase inventory.
Her mother Andrea is a frequent presence around the shop—regularly taking shifts behind the till.
“It was interesting managing employees as they were once my co-workers,” Blackwell said. “And the help of my mom was huge…I couldn’t have done this without her.”
Blackwell says one of the cool things has been watching the store’s following grow. Plus, she notes, you meet a lot of great people.
“It’s been really rewarding,” she said, noting that she’s really appreciated how complimentary people have been.
One of the biggest accolades was getting nominated for—and then winning—a Best of Los Gatos award—three years in a row.
“It acts as a validation,” she said.
Blackwell’s mother says that she wants customers to know that, although the physical store front is closing by the end of this month, Jackie’O is here to stay: through their online presence.
“Retail always changes,” Andrea said, noting the key is to be versatile and adapt. “I always hear that we have really good quality pieces that are really unique.”
People comment on how their selection includes apparel with plenty of color at a good price point, she continues.
“We don’t fit just one type of girl,” Jaclyn said.
“We sell from girly-girls to edgy, and an age demographic from 18-70,” says her daughter.
It seems that the mother-daughter duo that holds the store up is a fair representation for the buyers as well.
Blackwell remarked on the time a 16-year-old girl and a woman in her 70s came in and purchased the same dress.
Theft in retail
One of the serious challenges Jackie ‘O had to deal with? Theft.
“That was something that really shook me up in the beginning,” Blackwell said.
She realized that, in order to run the shop effectively, she’d have to stand up for herself and confront thieves.
Blackwell recalled a time when a woman attempted to throw her off, while shopping, by picking up multiple sizes of the same dress.
She says the lady hadn’t returned all the items and had stepped out onto the North Santa Cruz Avenue sidewalk.
Blackwell raced outdoors to demand her item back. She also told the shopper how disappointed she was in her behavior, she recalled.
And she became involved in an effort amongst the downtown business community to harden themselves against the scourge of retail theft.
They communicate with one another when a break-in or stealing incident happens, so the suspect is immediately on everyone’s radar.
The retailers banded together, in part because of the recent reclassification (via Prop 47, 2014) of some felonies (involving stolen property worth up to $950) as misdemeanors, Andrea said.
Blackwell and her mother completed an online course on running an e-commerce site.
They learned about the ins-and-outs of digital ads, and how to target the right audience. And they’re looking at reducing their reliance on middle men.
Blackwell says over the years they’ve seen less foot traffic.
She attributes this, in part, to a drop in business customers coming in, due to the uptick in people working from home, and people avoiding going out due to beachgoers en route to Santa Cruz or Monterey clogging streets. “Saturdays are always our best days, and in the summer time they are our worst days,” Blackwell said, stating that the town needs to find a solution.
Blackwell says that when she was taking the online course last year, the landlord raised their rent by 50%.
She decided it was time to move their operation completely online.
“We knew we had to tell the landlord two months ago on whether we wanted to renew or not, and we came to the decision to leave the storefront,” she said.
Both Blackwell and her mother say that the decision has left them both very sad.
They’ve gone through all the waves of highs and lows—from making customer connections and even hosting pop-ups, to making it through the Covid-19 pandemic and watching the political winds change direction around them, as well.
Blackwell says, these past few years, she’s grown a lot. And she’s really grateful for everything she’s gained during her tenure at 48 N. Santa Cruz Ave.
Blackwell’s next move is to work in recruiting in San Diego while she still maintains her online presence. She says she’ll be bringing plenty of communications and sales skills along with her.
The closing of the store is slated for July 30. All items are 40% off until then.
East Kennedy
Sharing a wall with Jackie’O is a retailer with an eclectic history by the name of East Kennedy.
Hayley Aurelio grew up in Los Gatos in the neighborhood of East Kennedy off of Kennedy Road—hence the name.
She began working on the business venture in 2014.
“We started with staging and interior design as a start, and became a retail store in 2019,” she said. “In July of 2020, we moved onto North Santa Cruz Avenue—moving from village lane.”
During their Village Lane days, Aurelio would host parties (including a champagne and braid bar) to bring in traffic, which helped to build their community.
She opened a retail store that primarily featured homewares and gifts in 2019.
At the end of 2020, Aurelio expanded into apparel.
Aurelio also designed the bar “Number 1 Broadway,” located above Rural Supply downtown, doing their interior planning.
It got to the point where Aurelio says she couldn’t be in the store during the day, so she stopped taking private clients in 2022.
Instead, she turned her attention to bringing in new offerings to her store.
Aurelio says she sees the town changing.
There is less emphasis on community, she opines.
She says a lot of things are different now, after the pandemic.
“In the beginning of opening on North Santa Cruz Avenue, we did have attendance in the parties we threw, and people were craving to be around other people—since we were locked away for so long,” she said. “But eventually, there was this shift.”
Aurelio says she’s considering moving out of Los Gatos entirely.
“My dream was to live in a Hallmark town and own my own boutique,” she said. “And that can’t happen anymore.”
Of course, the rent hike was a big factor (they share a landlord with Jackie ‘O).
Aurelio says they’re already up-and-running online—and they’ll still do private styling.
That’s not to say that they won’t reemerge as a brick and mortar, at some point in the future.
Aurelio says she’s definitely enjoyed running a business with a storefront.
But, at least for now, she sees a town in transition, and she says she’ll wait to see what happens.
“Los Gatos is my home, where I had my children and where my family lived,” she said. “I wanted this store to be a place for my kids to work at while they are in school.”
That plan is on pause, for now.
The reason that she and her husband moved back from Los Angeles was for the sense of community and because of how safe it is compared to other areas.
But Aurelio is concerned about the shifting small-town balance.
To her customers over the years, Aurelio says, “We are so grateful for their support and believing in us—and making this little dream work, for half a decade. And we’re still around!”
*The article was updated to clarify Andrea Blackwell’s description of why downtown retailers banded together.
