Brandon Holley is a style survivor, a refugee from a golden age when slick, thick women’s magazines dominated fashion, from the runways to retail to consumer closets.
As editor-in-chief of iconic publications Lucky, Jane and Elle Girl during the 2000s, Holley honed a shrewd eye for what women want and how women shop.
Then she watched fashion content go digital, decimating many famous magazines and ending the brands she once led. But Holley, now 51, emerged from that disruption with her own digital styling venture – Everywear – and a lifetime supply of hard-won wisdom.
“Here’s what I learned: women shop online differently,” Holley says. “For example, men don’t want to see one red blouse matched with 50 things you own. That would drive men crazy. Women want to see it. I realized that e-commerce was invented by men and needs a female rethink.
“Women were being forced to shop online in a way that isn’t the way we like to shop. That’s why women bought magazines. They want to see images and beauty. The magazines went away. But the behavior and psychology didn’t. I am now bringing those together.”
In 2015, Holley founded Everywear, the first platform that applies editorial authority to e-commerce through personalized recommendations. The company’s snappy tagline: “Technology that thinks like a fashion editor.”
The software-as-a-service solution lives on the websites of Everywear’s four large retail partners, including Bergdorf Goodman, increasing sales conversion rates and predicting future purchase behaviors of online shoppers, Holley says.
Consumers who engage with the platform on those sites complete a short form that lists the fashion “basics” already in their closets, including shoes, jeans, jackets, skirts, tops, pants and accessories like jewelry and handbags.
The listed pieces of attire become data points. That information, in turn, generate images that represent each fashion “basic.” Finally, it’s math time.
“We created an algorithm that reads your psychological wardrobe with these images,” Holley says. “We use it to leverage that consumer’s preferences against the inventory at a retail partner, and we create one-to-one results for them.
“The algorithm is built on rules that I used on-set for models and celebrities.”
After a consumer enters her closet contents, Everywear picks matching pieces of attire from the retailer’s product page – say, a plum-colored jacket. It then shows the customer how that jacket would pair with some of her own “basics” – like a white blouse and black pencil skirt. Using those looks, it instantly creates several outfits for work, nights out and weekend hangouts.
Everywear has collected more than 2 million pieces of data from the closets of about 120,000 women who have used the platform. Those consumers have clicked on merchandise that’s worth, in total, almost $100 million, Holley says.
“This is in the very first stages of what will lead to machine learning on style,” she says.
In at least one pilot, the average sales-conversion rate was five times higher among shoppers using Eveywear as compared to shoppers who didn’t access the platform, Holley says, and the users’ average order value was three times larger compared to shoppers who didn’t try the service.
Those early results only reinforced Holley’s opening premise – that e-commerce companies made product searches simple yet forgot to streamline the art of apparel shopping.
“Everywear is like when you walk into a boutique store and that salesperson says, ‘Hey, how’s that top you bought? Did you try it with those jeans?’ Because she also knows the other things you have in your closet,” Holley says.
“The data we are collecting is insane,” she adds. “We know, for instance, that if a customer at one of our retail partners is in her 20s and owns skinny jeans, she will most likely want to shop for shoes when looking for weekend wear. As we hone this to an even finer point, it’s going to change e-commerce.”
Based in the New York City area, Everywear numbers four employees, all women: a head of product, a stylist, a chief technology officer, and Holley, who describes herself as “a hustling CEO.”
Since June 2017, Everywear has worked within Microsoft’s startup environment – and individually with Tereza Nemessanyi, a Microsoft partner business evangelist.
Through that collaboration, Everywear attracted venture capital funding, met top advertisers, approached new clients, and streamlined its enterprise sales cycle, Holley says.
“It’s an example of how Microsoft is working with startups at the flash point,” Holley says. “We’re early but our solution is already being used at some very large retailers.
“For Tereza to pick my tiny company out of a crowd, it’s advantageous to us. But it also helps the retailers because they get first access to innovation. It positions Microsoft as an important magnet.”
Nemessanyi says she recognized Holley as “one of the top style editors on the planet” during her stint leading Lucky from 2010 to 2013. (Holley was the editor-in-chief of Jane from 2005 to 2007, and Elle Girl from 2000 to 2005.)
“The idea of ‘productizing’ Brandon’s vast style knowledge into a dynamic algorithm really blew me away – imagine the scale of millions of shoppers being able to have a one-on-one with Brandon,” Nemessanyi says.
“This type of insight is delightful to the consumer and can strongly drive purchase decisions,” adds Nemessanyi. She also introduced Holley and her team to Microsoft Azure, prompting a plan to move Everywear’s data to the Microsoft cloud computing service.
The Microsoft for Startups program gives fledgling companies access to technology, providing go-to-market benefits and fueling growth of their customer and revenue bases.
Microsoft is committing $500 million over the next two years to offer joint sales engagements with startups as well as access to Microsoft technology and to new community spaces that speed collaboration across local and global ecosystems.
That support is helping Holley realize the entrepreneurial inspiration that struck her a decade ago in Milan, Italy while shopping with a fellow editor. They were strolling through a fancy store when a belt costing 1,200 euros (about $1,500) caught Holley’s eye.
“Brandon, don’t buy that,” her editor-friend said. “Buy this.”
The editor grabbed a far-less-expensive V-neck sweater.
“This is going to go with your Prada skirt,” she said, before listing a dozen more ways Holley would wear that sweater.
Ten years later, the sweater remains in her wardrobe. Each time she dons it, she silently thanks her friend for steering the purchase.
“After the moment, I thought: What if everybody could shop with a little Lucky editor on her shoulder? What if everybody, while they shop, could hear the words? ‘Wait, wait, wait, that’s not what you need. This is what you need.’”
Top photo: Lucky magazine hosts FABB: Fashion and Beauty Blog Conference, presented by P&G Beauty & Grooming. Getty Images. All other images courtesy of Everywear.