What It Cost Me offers a glimpse into the real lives of fashion-forward creatives building something on their own terms and the choices it takes to keep going. From managing personal finances to navigating time, discipline, and delayed wins, the series reveals the investments behind creative independence. Rooted in that same pursuit, Ally Bank brings personal financial tools and resources to help a new generation build for what’s next without losing sight of life today. Keep scrolling to meet the cultural forces turning their vision into something real.
For some, nostalgia is just a feeling, but for Advisry’s Keith Herron, it’s a mode of operation functioning as a layered system where West Coast wearability meets East Coast style sensibilities.
With beginnings that broke the mold, the brand sprang from the precocious mind of a middle school whiz kid, emboldened by his entrepreneurial mother to pursue his passions. It started with some simple investments: a few boxes of $2 blank tees, a $90 heat press machine, and $30 worth of heat transfer paper, laying the foundation for the teenager to turn his brainchild into the contemporary interpretation of street style it is today.
This is a story that Herron — now 26 — has told countless times, but the vision remains clear: create as much as you consume. While the brand’s early days required more tangible financing and material resources, these days, it’s about more than just monetary matters or production supplies for the creative polymath.
“I’ve always been invested in [Advisry]; I would fund it by reselling clothes before the brand even had any customers,” he recalls. “[That said,] I consider it an investment any time I practice self-care, contribute to cultural conversations, go into a bookstore, or watch a movie in the cinema — anything that makes me really happy or waters my creativity,” he continues.
These practices become something of a sacred ritual for the creative force, and although spearheading Advisry comes with a set of sacrifices, both personal and financial, the reward has always been worth the risk. Even with its irregularities and inconsistencies at times, a path as inimitable as Herron’s is enticing to aspiring creatives. Cognizant of what comes with a career fraught with unpredictability, Ally Bank, the new-age digital bank, is helping a new generation of nonconformists work through the wrinkles of life and money.
A true disruptor in the financial services industry as one of the first online-only banks, Ally arrives with a new platform, “Life Today,” dedicated to tackling the nuanced reality of how Gen Z and millennials are spending and saving for their dreams. The digital bank isn’t solely concerned with guiding young people through their cash challenges today, but also tomorrow and someday with smart savings tools and groundbreaking personal financial education. As a next-gen trailblazer himself, navigating the ebbs and flows of his chosen craft, Herron has Ally as an asset in his corner to support his personal financial needs while building his brand and giving him the confidence, clarity, and control he needs to continue to redefine what it means to attain financial freedom as an artist.
“[I think] most artists strive for a level of personal financial freedom where you’re able to dream about certain concepts and not have to pitch them to someone else in order to make sure it happens,” he notes. “You can be on the fashion calendar to do a runway show, but then, how do you pay for that? You have to spend months talking to different people, raising money in order to do it,” he adds. “I have the luxury with this new collection that we didn’t have to pitch it — I was just able to come up with ideas, and now they’re in motion.”
As he moves closer to his aspirations of complete autonomy — reaping rewards from over a decade of dedication — Herron hasn’t forgotten the early days when, without the resources he has today, he experienced his fair share of hardships and critiques.
“The feedback wasn’t very good at the beginning. People would question certain choices or the quality of things; at a certain point, I got sick of it,” he recalls. “I knew where I wanted to go and what I wanted to do, but I felt like I was being judged before I could reach my own potential. So, I blocked everyone I knew because I wanted to be measured on a scale beyond my school and my city.”
Transcending the limitations that once stifled his self-expression and creative output, the modern renaissance man’s creations swiftly reached the eyes and ears of those he revered most. That journey culminated in an appearance on the NYFW calendar – not once, not twice, but three times — and a Met Gala moment with local NYC politician Chi Ossé. Milestones now cemented in his career, Herron’s enduring success is a culmination of sacrificing both the intangible — time and energy — and the tangible, representing the very moments he’s worked his whole life for.
Yet, like any artist, he’s nowhere near slowing down. With so much more on the horizon for Advisry and his other passion projects — a feature film is still sitting on the shelf — Herron is finally in a position to dream first and worry about the dollars later. For now, however, the brand’s next collection is his main focus, with newfound creative latitude reflected in the brand’s expansion into wholesale, product presence in physical stores, and the ongoing cultivation of his brand voice.
As he’s poised to return to the runway for his fourth time on the CFDA fashion calendar this September, Herron’s 12-year story proves that no path is linear, but every path is singular, and his continues to unfold.
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