The Most Powerful Style Advice for Work, According to a Female Entrepreneur


Here at Who What Wear, we’re champions of female-founded, -owned, and -operated businesses—after all, our company was founded by two fearless women. That’s why we’re launching Female Founded, a new editorial series that dives into the stories of those who launched their own businesses. Here you’ll discover who these women are, what they've accomplished, and how they style pieces from our own Who What Wear collection at Target.

Recently, I looked at my bank statement and noticed a common thread between the companies I give most of my money to. Uber, Glossier, Drybar: They all try to give you the most by doing the least. What I mean is they didn't set out to be everything to everyone, instead narrowing in on a single service or category. That's certainly the route Alli Webb took a decade ago when she launched her pillar in my bar graph of spending, Drybar. Personally, I don't know what I would have done for countless interviews and events had it not been for the ability to walk into my local Drybar blowout salon sans appointment and leave 30 minutes later with perfectly styled strands.

Drybar's success undoubtedly lies in the fact that Webb had been a professional hairstylist for almost 20 years before its start. It wasn't until 2008, at which point she'd most recently been a stay-at-home mom to her two kids, that she started her first business, Straight at Home, a mobile blowout service that would to some extent inspire her most prominent venture to date, Drybar. Well, 100-plus locations, 3000 employees, and a growing product line later, Webb claims a number of high-profile accolades, including Fortune's 40 Under 40 list and Fast Company's 100 Most Creative People in Business lineup.

Ahead, Webb reflects on her trajectory, offering advice for fellow female entrepreneurs and tips for investing wisely in a work wardrobe—all while expertly styling pieces from our Who What Wear collection.


(Image credit: On Alli Webb: Who What Wear Short Shirred Sleeve Dress ($33); Miu Miu boots)

On how to (actually) invest in a work wardrobe

Webb knows better than anyone just how busy our lives can be these days. After all, Drybar is the solution for so many busy women (myself included) who want salon-quality hairstyling without spending hours on end in a stylist's chair or succumbing to the price tag that comes with it. Her idea is to cut through everything you don't need to bring you everything you do (i.e., a great blowout).

Well, the same can be said about curating a stylish and actually functional work wardrobe. It's all about knowing which pieces to invest in and which to buy on the cheap, something Webb hits the nail on the head with. "I think the key is clothes that fit really well and work together," she advises. "They don't have to be expensive." Case in point: our $33 Short Shirred Sleeve Dress, which Webb styled to perfection with a sleek pair of lace-up Miu Miu boots.


On power dressing

Power dressing takes on a whole new meaning if you're a female founder, which is why it's been a common theme throughout our series of interviews. Entrepreneurial women know better than most that you have to dress for the job you want, not the one you have, because when you launch your own business, you're creating a role that literally didn't exist before. Dress codes are thrown out the window, and it's ultimately up to you to label and channel your power, both in what you do and how you present yourself. It's nothing if not aspirational.

"Dress like you're about to meet the most important person in your life," Webb declares. A combination of comfort and polish comes to mind, perfectly manifested in her below outfit, wherein the sophistication of checkered trousers and sleek boots meets the ease of your favorite sweater. We'd imagine this is how Webb does power dressing, though if she had to interview for a new job today, she tells us she'd opt for something more structured, like a fitted suit.


(Image credit: On Alli Webb: Who What Wear Long Puff Sleeve Crew Neck Sweater ($30) and Plaid Wide Leg Cropped Suiting Pants ($35); Celine boots)

On her advice for female entrepreneurs

Fear is a crippling part of any venture involving risk, but if we all went around letting our fear get in the way, where would we be? This is the mindset Webb has taken with Drybar, and though it seems like an intuitive one, it wouldn't hurt for anyone launching a business (or, really, with goals of any kind) to hear once more: "Just start," she says, "and don't worry that you don't have all the answers yet."

Webb may have more answers now, after years in business, but like anyone, she's made a few mistakes and will be the first to admit they were crucial lessons. "As a young adult, I would often just blurt out answers or opinions without considering the consequences. I think as I got older and wiser, I learned how to balance that urge to have such a strong knee-jerk reaction to everything," she says.

Composure is key, but for Webb, it's also crucial not to be too closed off. "I think being open to feedback is probably the best advice I've ever been given," she tells us. "It's tough but so very important to your growth and development as a businesswoman and human."


On the legacy she wants to leave behind

For those starting their own business, thinking about starting their own business, or even holding onto the distant hope of one day doing so, it's important to have mentors for inspiration and guidance. Of course, anyone with a dream (so, all of us) can name some people who've influenced their lives at one point or another, but it's those like Webb—those who've dared to chase after that dream so courageously, so determinedly—who can rattle off their mentors as if it's second nature.

Webb's personal sources of inspiration seem to mirror the short list of Very Important Women throughout modern history: Jackie O., Maria Shriver, Maya Angelou, Oprah, Princess Diana. While these endlessly influential women have granted Webb the courage to launch Drybar, she's certainly earned enough prestige of her own to be the mentor that future business leaders rattle off one day—and she'd love nothing more. "I hope," she tells us, "to inspire and empower a new generation of female entrepreneurs to chase their dreams."


(Image credit: On Alli Webb: Who What Wear Striped Long Wide Sleeve Pullover Sweater ($33); Rachel Comey jeans; Manolo Blahnik pumps)

Shop more work-ready pieces from the collection:

Shop Webb's look:

Photographer: Paley Fairman | Makeup Artist: Dana Delaney | Stylist: Yasi Moshtael


Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.