Lesley Ware fondly remembers how New York Fashion Week used to be. The designer, boutique owner and lifelong educator was acclimating to the city in the mid-2000s when the early voices of the fashion blogosphere were changing the ways that the industry interacted with its members and consumers. In 2008, when Ware was working as a Girl Scouts programs manager, she joined the growing oeuvre of fashion voices using digital media to add her perspective on industry behind-the-scenes happenings with her blog The Creative Cookie.
The next five years were Ware’s coming-of-age adoption into the New York City multi-hyphenate lifestyle. By day, she channeled her early childhood education background to develop youth enrichment programs, while her evenings were spent tutoring and working in retail, dividing her time between Anthropologie and American Apparel. These conditions under which she developed her creative voice were a part of a well-documented moment in New York’s fashion history, just at the precipice of online hypervisibility and sustaining shifts in merchandising practices that affect how we engage with clothing to this day. The culmination of her artistic curation is currently on view at her Art to Ware storefronts.
Ware remembers these times from the bench of a chicly understated Bedford Stuyvesant cafe just blocks from where she now lives with her husband and cat, Miles. Her signature tinted horned eyeglasses and vermillion trench coat are reminiscent of the same style that became her signature in the world of 2010s fashion eclecticism. As she reflects on these formative times, the mid-morning vibrancy in the shop begins to match that of her true-to-life storytelling.
Ware’s present conversation reflects the referential cycle of Brooklyn cool that attracted her to the area in the first place. From her seat at the minimalist Che—the chic offshoot cafe of Tompkins Avenue’s Sincerely, Tommy—she begins to reflect on what she used to see during her Bryant Park lunch breaks. Every day, she would watch the garment-filled clothing racks zip through the midtown crosswalks surrounding her former office, ideating content for The Creative Cookie, and soon, sharing fashion week rows with the likes of Tavi Gevinson.
After five years spent with the Girl Scouts, Lesley was ready to dedicate more time to her creative ventures. In her search for flexible work, she landed on another longtime city institution: Craigslist. Classified ads for children’s sewing lessons soon landed her in the Upper East Side private tutoring market, where she established a new art student base.
“It felt like teaching and then blogging by night was like the way to go,” she tells ESSENCE.com. Throughout this period, Ware was also developing her manuscript for her first book, Sew Fab: Sewing and Style for Young Fashionistas. Being involved in education in this new context reinforced Ware’s mission to empower tweens and young adults. Guiding predominantly white kids in the Upper East Side also recentered her mission to make sewing resources accessible for girls that looked like her, so they could also visualize themselves within the expansiveness of the fashion world. By May of 2013, she had a pitch ready for the annual Book Expo.
“I had my manuscript that I had been working on and knew the writers and publishers I wanted to meet,” Ware tells ESSENCE.com. “I was walking up to the tables, and was looking for the ones who would publish something like the books that I had in my brain for all these years.” Within six months, Ware had signed her first book deal.
Lesley’s books are an extension of her in-person teaching approach, which encourages students to find playfulness in their craft. From sourcing materials to brainstorming, and eventual execution, fashion design is framed as an act of self-actualization that doubles as a sustaining life skill. Centrally, though, it is supposed to be fun. Sew Fab and its immediate follow-up, My Fab Fashion File were personal-style sketchbooks that prompted users to “create and record your dream looks.”
The idea of someday opening a store was a transient thought in Lesley’s mind, but for most of the years leading to the COVID-19 pandemic, she was focusing on teaching, writing, and publishing. The intersections of her work allowed her to ideate her own upcycled creative label, even as the city waded through months-long tragedy. The induced calm of an emptied city offered a period of recalculation for the fashion educator, as she reflected on the city she’d come to know and the ways it was changing. Though the exchange vehicles were in flux, Lesley Ware recognized that the desire to learn and participate in the vibrant scene would return, as it always does.
With four books under her belt and over a decade of teaching experience, Lesley applied to a storefront accelerator program while also penning her fifth and latest book, Blacks Girl Sew. This most recent offering was a dedicated teaching guide to inspire fashion aspirations in Black girls, showing them how convergences in style history, sewing instruction, and environmentally ethical sourcing practices sew a unique tapestry of conscious creation. Following a foreword by former ESSENCE editor, Constance C.R. White, Ware writes, “We want you to get tangled up in the magic of creating fashion through the projects in this book, and then go further.”
As Ware inspired her young audience, she was taking her own advice and envisioning a new role for her in the fashion ecosystem—one that would denote a more permanent physical presence. She developed her Art to Ware business plan with the help of Chashama, an arts enfranchisement foundation founded by philanthropist Anita Durst. The organization has matched creatives with free or discounted space studio and sales space since 1995 and opened their network to a hand-selected cohort in the early days coming out of the pandemic. In a period when many brick-and-mortar stores were forced to go virtual or shutter altogether, Lesley Ware and other aspiring store owners were able to focus on growing their labels without the hanging anxieties of acquiring and maintaining retail space.
Since 2021, after launching Art to Ware as a pop-up in the Port-Authority terminal mall, Ware has been operating one store there and one within the Westfield World Trade Center in the Oculus. Both locations operate as shoppable showrooms of ethically sourced clothing and wearable art. By spotlighting the talents of emerging artists and maintaining accessible pipelines to inclusive participation in the fashion space, Ware is living in her doctrine that cultivating taste is a community effort. When asked how she identifies who to merchandise from, Ware replies, “Most of them find me.”
In over seventeen years of carving out her distinctive path, Ware has watched the pipeline of the fashion industry proliferation cycle through multiple pivotal moments, entering just as bloggers emerged as bridges to the gap between outside enthusiasts and industry insiders. Adapting her background as both a seamstress and educator to the rapidly evolving digital landscape, she embodied the diverse intersections that make fashion such a compelling and interdisciplinary field. Through her books, brand, and storefronts, Lesley embodies the essence of New York’s sartorial culture, continuously evolving to captivate future generations of style aficionados.
In a fitting testament to the cycles of style, Lesley is now considering going back to her blogging roots, seeing how it can help her chronologize this matured, more established phase of life. “I get the question of what’s next like once a week. I think maybe it’s something that doesn’t even exist yet,” she said. “I feel like everything I’ve said I wanted to do, I was able to do by about 45, but I know I’m going to write more books. I want Art to Ware to grow, and I still think there is another piece of the puzzle. I don’t know exactly what I have to say but I’m just going to do it. Here I am, 17 years later and I think that’ll help me—going back to the origins of my creative journey.”
Until that next chapter is revealed, interested shoppers can find Art to Ware at either of their two Manhattan store locations. Until a suggested relaunch of The Creative Cookie releases on Substack, readers can find Lesley Ware’s writing in all five of her books, available online.
