How the Founders of WhoWhatWear Changed the Beauty Game

If there’s anyone who knows how to make a major and wildly successful career change look easy, it’s Hillary Kerr and Katherine Power. For almost 10 years now, the dream team behind Clique Media Group (does WhoWhatWear, their pioneer domain and one of the first fashion darlings of the online media industry, ring any bells?), has been changing the beauty game one goal, project and website at a time.

Former fashion editors themselves, the two went from positions like freelancing writer for publications such as ELLE, Teen Vogue, and Nylon (in Hillary’s case), and West Coast ELLE editor (in Katherine’s case) to starting their own online business and brand from the ground up.

Now at the top of their game, the two have officially released their very first clothing line exclusively at Target, and took some time out of their hectic schedules to talk business with me at last weekend’s Create + Cultivate Dallas, a premier fashion conference seeking to inform and entertain female entrepreneurs in the digital space. They then went on to appear and speak on their successes as the final keynote panel of the evening, just in case you were wondering.

Needless to say, I was inordinately excited to talk to Hillary and Katherine about a variety of topics – first and foremost how they’ve completely slayed the game beauty-wise, both online and off.

One thing you think every young professional should have in mind when first starting to build their personal brand?

KP: Definitely a unique point of view, I think that’s the number one core element to focus on. What is your point of view, and how is it different from whatever is out there? And I think that’s good for any business, whether it’s opening a restaurant, or creating a blog, or coming up with some sort of consumer [base].

HK: Storytelling.

What’s the best thing that you can do to stand out when it comes to being an influencer, or looking to become one?

HK: I think coming from a [cohesive] point of view, as well, it’s like conditioned to knowing what you stand for – really thinking things through, and understanding, What does my brand stand for in terms of visuals, what does it stand for in terms of color, what does it stand for in terms of font?

Overall aesthetic.

Yeah, just overall aesthetic, I think that’s really important because even if someone’s not reading your captions or reading your stories, or listening to you talk on SnapChat, or actually really digesting your work instead of just glancing at it – which a lot of people do, especially in this busy world – you want your visual language to be just as articulate as the words you choose. And to really just further the story that you’re trying to tell.

Make it impactful and engage with your reader.

You can’t always be 100%; I think sometimes it gets a little affected if you see something and it’s like, only in shades of purple. How you communicate that effectively through imagery is really important.

(Editor’s note: HK and KP may or may not have noticed that this particular editor has purple hair.)

What’s your advice on coming back from professional failure or a major career change?

Because I know you both did that – not fail, of course (at which point I was completely mortified), but make a major career change.

[both laughing]

KP: For us our career change was in the same field; [so] we just sort of took the principles of what we were doing in print and re-imagined a way to do that on the Internet. I think it’s more challenging when you are actually wanting to completely switch career fields, but I think the same idea could apply; where there was nothing about us that said we were experts in the Internet. We had to show people that.

Right, and this was also at a time when it wasn’t as prevalent as it is now.

KP: Oh, people thought we were crazy. Straight up. We didn’t know anything about the Internet, but we knew that we could create a great product on the Internet, so we just went [ahead] and did it. I think it’s very hard to switch if you’re an adult and you wanna switch industries completely, it’s hard to break in because you know, as an employer, we look at people who have a very specific skill set or experience we’re trying to fill.

But I think that there is an opportunity to show people that you actually are good at something, and the Internet makes that really easy! Whether it’s creating your own blog to showcase your point of view, or your expertise in something – whether it’s cooking or fashion or music. Or creating a Pinterest page. It’s kind of about creating your own body of work to show, even if you’ve never actually been paid to do that.

HK: I think part of that too, [is that] people get very nervous about changing careers. And they feel like “Oh, I could never do that,” but really, in a lot of ways, there are so many skills that directly translate from career field to career field in terms of things that we look for. Are you resourceful? Are you able to create efficient projects? Can you communicate clearly? There are certain things that if you sort of reframe – like yes, you were doing this for a different company, but what were the underlying skills that are [key] to any industry, and that will help you sort of navigate the waters?

Ways to use insecurity or inexperience in the workplace as an asset?

HK: If you really want a change and you want to pursue this other line of work, when you’re truly passionate about something nothing’s going to stop you. And you’re gonna do it no matter whether you’re being paid or not. Just because there’s this thing inside you that says I have to do this. And if you can’t be bothered to put in the work, then why should anyone [else] be bothered?

Or to read your work, you know?

HK: Yeah, because a lot of people say, “Oh I’d love to do this, I’d love to do this,” but they don’t do it, so therefore, what does it matter? It’s just talk.

What’s the standout personality trait you feel you both have that took you to where you both stand today?

HK: We’re hard workers.

KP: I think for me it’s courage. I don’t have that fear of change that says I should be worried about what people think.

HK: And I would say I’m never afraid of hard work; I don’t turn away if something seems bumpy or difficult. It makes me double down, I actually kind of get more stubborn when it comes to making something work sometimes, certainly when it comes to career stuff. Because I feel like there’s a way to make just about anything work, and if I haven’t figured out the solution yet, then that’s sort of my obsession then.

This isn’t one of my planned questions, but what’s your sign?

HK: I’m a Virgo. And she’s a Taurus. [laughing]

Oh, that explains a lot! How perfect. You’re like the perfect pair, that’s amazing. I was genuinely curious when you said that, because that’s such a Virgo thing to say.

What’s the most important thing you learned from your background as fashion writers and editors?

HK: Storytelling, really. At the end of the day, looking at a collection, being able to translate it so that you can explain it to other people who might not care about fashion or be obsessed with fashion. Being able to say what this is about, this is why it’s important, and this is how you can adapt it to your body or your style or your budget or whatever it is. This is one of those very fundamental things that we were doing early on when we were still writing every single daily story. Brand-building.

KP: Coming from a more corporate structure and being able to apply certain best practices or processes into a business that otherwise had no structure. Just starting this, there was no example of even the online media industry at that time.

You definitely had to forge your own path, that’s for sure.

KP: Yeah. But we had some sort of starting point as far as how to structure the team and business.

HK: We knew we could also look at our past experiences too, and know what worked and what didn’t work and what we would change. And then we [used that] to sort of cherry pick the best parts of more traditional media and the corporate world, and combine [to find] what was right for us and our company, and our brand. The remix!

What’s one thing you would have done differently?

KP: I don’t think there’s anything I would have done differently.

HK: I mean, it happened the way that it happened, and we learned the best things that we learned along the way at appropriate times. I think that it’s like that Sliding Doors aspect [you know, that Gwyneth Paltrow movie]. I use this reference all the time, I don’t know why, but it’s the idea that you miss the train, you don’t make it through the door, and your life can take one entirely different path.

Oh, like the Butterfly Effect.

Right, [it’s like] choose your own adventure. If we changed any one thing, that would also mean a zillion other things change, so… and it’s been fascinating, and overwhelming, and enriching, and difficult, and rewarding all at the same time. I feel like we’ve learned such valuable lessons every step of the way.

At Livingly, we strive to “live life beautifully.” What does living beautifully mean to you?

HK: Balance.

KP: That’s what I was just gonna say!

[both laughing]

Virgo and Taurus!

HK: Though we both find balance in different ways, I think we both have this idea that you have to balance work with off-duty time, and you have to take care of yourself, and you can’t be up all night or [at] work all the time and not expect that to have some consequences. You have to have things to look forward to, and you have to have some organization in your life to help mitigate some of the stress; and you have to find your outlet for stress. You have to find your outlet for what fills the creative well back up.

I think at the end of the day finding that balance is everything. There’s a lot to be said for a quiet night on the couch. [You should be] always striving to figure out how you can be the healthiest and that is physically, and emotionally, and [environmentally,] and not in a punitive way, like, “Oh, I have to abstain from all of these things, because that’s healthy,” but some of those things, yeah.

If they’re not adding to your life or contributing to your growth, you should probably cut them out at some point.

HK: Yeah, it’s just like, toxic friendships, or toxic habits, or whatever it is. You have to figure out, is this additive and healthy, or is this taking something away? And it’s not always fun.

I don’t think that part is fun at all, but yeah, it’s definitely something I’m learning.

HK: I think it’s interesting realizing you can be many selves in a lifetime, in a week, in whatever it is; there’s always sort of that tipping point and you come to an equilibrium, and it tips again, and you learn something else… Knowing that nothing you do will stay the same, nor should it, is a [big] thing. Who wants to stop growing? I mean, if you don’t change, you’re a dinosaur, and we know what happened to them.

...Well actually, they’re in museums, so.

Who knows, maybe we’ll see WhoWhatWear in a museum one day!

Be sure to check out the power duo’s gorgeous new clothing line designed exclusively for Target, available in stores now.