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Five years after launching High Sport with a pair of $860 cropped kick-flare pants that became one of fashion’s most unlikely cult items, Alissa Zachary is ready for a bigger stage.
For spring 2027, the Los Angeles-based brand will join New York Fashion Week for the first time, releasing a digital lookbook that’s a prelude to what comes next—the runway. It’s a significant milestone for a label that has grown largely through word of mouth, without ever staging a party or press day, let alone a fashion show. And it comes as Zachary is preparing for High Sport’s next phase of growth, including category and retail expansion, creating a physical home for the brand in LA, and eventually, perhaps, taking on outside investment.
“We’re excited to bring the brand to life and bring the community together,” Zachary says. “We have not even scratched the surface, which is exciting, because we have so much potential.”
Just days before going to New York, Zachary is sitting in High Sport’s showroom in Almont Yard in West Hollywood, a discreet creative compound with a leafy courtyard. She leased the space about a year ago, and it still feels more like a working studio than the debut store it will become, with a moodboard full of clippings behind her desk and an impressive collection of research books scattered about, from Anna Thommesen: Weavings surveying the work of the Danish artist, to Kevin O’Sullivan’s Goin’ Big: Gotcha and the Evolution of Modern Surf Style about the pioneering 1980s Southern California surfwear brand.
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There is Zachary’s version of the little black dress that’s devastatingly sexy and body-skimming but not shrink-wrapping; the perfect black jacket with a controlled peplum that’s tailoring made soft, and a pair of au courant hot pants in lemon yellow, worn with a baby blue graphic stretch poplin button-down shirt under a black sweater vest — a look that reads LA surf meets street.
For color and pattern inspiration, she looked at ’60s and ’70s Italian textiles, the daisy motifs in Japanese artist Yu Kobayashi’s work, which she saw at LA’s Sea View gallery, and John Chamberlain’s crumpled automobile sculptures. The interplay between structure and softness is a throughline.
“We started as a capsule wardrobe. The pants hit, which I couldn’t be more grateful for, and certainly that’s what we became known for out of the gate,” she says. “The way that we’ve expanded it is by adding new styles and fabrications beyond knits. This collection shows more of that.”
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The next phase is being built on a solid business. High Sport is posting mid-double-digit sales growth year-over-year and has 75 wholesale accounts, with Moda Operandi as its largest. This fall, it enters four Nordstrom stores in Bellevue, Washington; Century City and Walnut Creek, California; and New York City. Wholesale still represents the majority of sales, although e-commerce is growing, and Zachary runs it all with a team of fewer than 10.
Pants remain the largest category, followed by sweaters and tops. Zachary believes High Sport has already crossed an important threshold, from hero product to hero category. Customers who bought the original Kick pant — often in multiple colors — are now buying across seven new silhouettes.
“We see them all resonating, which is fabulous,” she says. “We would like to own that.”
Zachary grew up in Dallas and worked for The Row and Khaite in New York before moving to Los Angeles in 2017 when her husband took a job with Live Nation. The move gave her something she hadn’t had in two decades: a blank slate. “It was the first time in 20 years that I wasn’t working for someone else,” she says. “And yet I wanted and needed to work. And what was that going to look like?”
High Sport grew out of her desire for clothing that didn’t sacrifice polish for ease, and wouldn’t look like a wrinkled mess after a day of commuting, work, and kids. While Zachary doesn’t define it exclusively as a California brand, LA is embedded in it. “The light, the color, the anything-goes quality of dressing in LA,” she says. “I don’t know that California gets the credit for how much fashion has emerged and been born out of the West Coast lifestyle and the beach,” she says.
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But Zachary’s reference points roam well beyond California. She admires, for example, the intense focus and material innovation of Issey Miyake. And during High Sport’s development, a 1991 Vogue article by Susan Orlean on the history of Lycra became an important touchstone.
“Stretch gave women a lot of freedom,” Zachary points out.
High Sport’s version of that freedom is technically inspired and hit at just the right time in 2021, when people were still devoted to comfy clothes, but emerging from the pandemic and looking to spend money on fashion again. The signature compact knits require 18-gauge knitting machines that Zachary says are largely unavailable in the US, which is why Italy became essential to the business. Every one of the brand’s fabrics is custom developed, allowing the company to control not just color and pattern but structure and performance.
“We have a point of view about the form and function of clothing,” she says.
Now Zachary is beginning to think more expansively about how to communicate that. So far, Substack writers have been particularly important in promoting High Sport, she says, alongside editors, stylists and celebrities. Greta Lee wore a red, star-patterned High Sport halter dress to the London premiere of Toy Story 5. And Pedro Pascal brought another kind of attention when stylist Jamie Mizrahi put him in a High Sport poplin shirt and sweater for a Good Morning America appearance.
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One of the brand’s newest channels of growth and community is trunk shows. Last year, High Sport began experimenting with the format, staging three. This year, Zachary expects to do closer to 12, and next year she hopes to double that. They have taken place in homes, private clubs and hotel rooms, with successful stops in Aspen, the Hamptons and Palm Beach, among others, and Marin, Montecito, Houston and Miami on the itinerary.
They don’t yet represent a large percentage of sales, but Zachary sees them as an important customer-acquisition tool and, eventually, a meaningful business in their own right — one that can give High Sport a temporary physical presence in different cities without opening stores. “For me to be able to interact with the customer face to face, there’s no substitute for that,” she says.
Which brings us back to Almont Drive.
Later this year, Zachary plans to turn the discreet showroom into a shoppable studio where she can gather customers in a physical manifestation of her brand, to see, touch and try on the entire collection — something even High Sport’s wholesale partners can’t offer. It’s another step in turning a brand that has largely existed through product, imagery and word of mouth into an experience.
If the experiment works, Zachary hopes the business might eventually outgrow it and warrant a conventional storefront. She is also open to outside capital.
“I’m wide open to an inspiring and interesting partnership,” she says. “In the meantime, we have a very strong business, and we are growing in this super intentional and incremental way. I think that we can win by having a very clear vision.”
A New York Fashion Week IRL show or event is on the horizon for next year. And, since she imagines High Sport taking a woman from day to night, more eveningwear is in development, guided by the brand’s streamlined aesthetic. Menswear is another ambition, and eventually categories that have nothing to do with clothing.
“I want to lay such a strong foundation,” she says, “and for you as the customer to trust the brand so much that I could sell you a vodka soda, and you would believe that coming from me.”
For a designer who built a business by convincing women that the perfect pair of knit pants could be the ultimate luxury, perhaps a vodka soda isn’t such a stretch.
