While it's true we're in the business of style, we're equally as interested in the cool things our favorite women in cool clothes are up to. So when it comes to our workwear wardrobes, what better way to get inspired than by taking a look at the lives of some of fashion’s most successful women? That’s the idea behind our #hipowered series, in which we’ll be profiling chic professionals from every corner of our industry, from our own Who What Wear team to top Old Navy executives to leaders paving the way in creative startups.
What if we told you that everything you thought you knew about the fashion industry was wrong? We’re not saying there isn’t a grain of truth to The Devil Wears Prada, but the everyday reality of working in fashion isn’t all rubbing shoulders with designer bag–toting, Manolo heel–clicking women whose harried assistants are on one endless green-juice run. In our experience, the women who rise to the top are the ones who walk into the office earlier than everyone else, half-finished coffee in tow, ready to take on the day in fashionable yet accessible attire—and in sensible shoes.
To prove it, we turned the camera on two boss women making things happen here at Who What Wear. Shayna Kossove, SVP of ad sales, and Kat Collings, our editor in chief and executive director, invited us to follow along as they hurried through a regular day in the office. We talked about the best (and worst) career advice they ever received, how a perfect pair of jeans—here’s looking at you, Old Navy Power Jeans—is one of the most important elements of their work wardrobes, and how to combat the never-ending influx of meetings. Drumroll, please…
Kossove is a true Who What Wear veteran, having spearheaded Clique’s sales department more than a decade ago. What does her job entail? “I lead the sales team to make sure we’re meeting our goals and staying profitable, but I also love that I work with all areas of the company, including editorial,” she tells me.
Do the words “sales” and “goals” bring up unpleasant memories from high school econ? Kossove tells us there’s another side to her job that is often overlooked. “People may be surprised by how creative this job actually is,” she says. “It’s not just about being a seller and closing deals; it’s how you do it. We have to act as a marketing agency for our clients by ideating actual concepts for their ad campaigns. It’s not just numbers and spreadsheets.”
Then we have our editor in chief, Kat Collings, whose finger is constantly on the pulse of all things fashion. If we were in high school right now, we imagine she’d win not only Best Dressed but also Most Likely to Succeed—we’re talking about someone who got her start as our co-founder’s assistant 6 years ago, so it’s safe to say she knows the brand better than just about anyone.
“As editor in chief, I work with many of our internal departments, including content strategy, to map out the type of content we’re creating and to put together new formats for us to work smarter instead of harder. My job is to make sure each story is optimized to achieve what it’s intended to do and reach its full potential.” In other words, you know everything you read and love here? You can thank Collings for that.
Over the course of our careers, a lot of advice is thrown our way, and not all of it is helpful. But in a sea of clichés, there are a few gems worth hanging onto. While Collings’s is more about personal growth (she says that while creative work can seem glamorous, management is an invaluable skill to have), Kossove’s is more about the relationships you create along the way. “Never burn bridges,” she says. “The media world is small, and you will cross paths with people again.” Did you write that down?
Then there’s the advice that flops so hard you can almost hear it. Kossove’s might be the most frustrating, and it’s something a lot of working women will relate to. “I was once told that as a woman, you can’t have both a career and a child,” she tells me. “That’s not true because here I am flourishing in my career while being a mother at the same time.”
When Kossove graduated from college, she (like so many of us) felt an immense amount of pressure to land a job as quickly as possible. “My first job out of college was at O, The Oprah Magazine as an ad sales assistant. I was lucky enough to work for a great company—in my early years, I locked into in a place with a strong foundation. I always say it’s always so important to get your foundation at these large publishing houses and then move onto smaller startups. I helped start Who What Wear with Katherine and Hillary, and what really helped me is having the strong foundation of don’t-quit-until-you-make-it dedication I learned at these larger publishing houses,” Kossove explains.
Even if you’ve worked your way to the top, that doesn’t mean you’re not constantly inspired by other players in the game. “I admire people in the fashion industry who are powerful but somehow still very accessible,” says Collings. “Women who have a personal and direct connection to their audience—people like Pat McGrath, Leandra Medine, and Laura Bailey.” As for who she turns to for style inspiration, Collings tells us it’s none other than Yasmin Sewell. “Her outfits are effortless but always interesting,” Collings notes.
It should come as no surprise that denim is a key fixture in both Kossove’s and Collings’s wardrobes. Kossove tells us she abides by dressing in a way that makes her feel powerful. Her go-to? “Polished pieces like ankle-length straight leg jeans that show both your confidence and your capabilities,” she says. As for Collings’s advice? “Get creative where you can, whether you work in a more relaxed setting or more corporate,” she advises. “That may mean standout jewelry, or my personal favorite—out-of-the-box layering.”
If you had a hall pass for one day to do anything else, what would it be?
- “Something outdoors. I love to be in nature.” — Collings
- “Sleep.” — Kossove
How many unread emails do you have in your inbox right this second?
- “59—not a number I love. I am much happier with a nearly empty inbox.” — Collings
- “1522, so I’m jealous when someone has it in the single or double digits.” — Kossove
What are your thoughts on “dad” sneakers?
- “They look cool but not for me.” — Collings
- “Pass.” — Kossove
What’s your power track?
- “I love almost anything from Aretha Franklin.” — Collings
- “Material Girl.” — Kossove
Shop more of our favorite Old Navy jeans here.