Alegra O’Hare and Alexandra Waldman on Culture, Controversy and Viability in Fashion

Brandweek's One to One: a candid conversation between the Gap and Adidas veteran, and the co-founder of Universal Standard

Alexandra Waldman and Alegra O'Hare
Alexandra Waldman, the visionary co-founder of Universal Standard, and Alegra O'Hare, who helped build Adidas for 12 years and just left the Gap, interviewed each other in New York's SoHo neighborhood.
Photo by Cheril Sanchez for Adweek; Mural by Jochen Schliessler

We hear it all the time now: The tectonic plates of culture are shifting, changing the way all brands do business. And it’s hard to single out an industry more affected than fashion.

Whether it’s demanding size inclusivity and gender-neutral clothing or calling for slow fashion and sustainable packaging, shoppers are letting retailers, designers and magazines know they want the future of fashion to be more responsible and inclusive. Will legacy brands navigate the change and stay relevant? Can startup brands with big ideas break through? Which would you rather be?

We recruited two pros to ask each other the hard questions about this moment in fashion. Alegra O’Hare, who helped build Adidas for 12 years and just left the Gap after a year with the 50-year-old retailer, and Alexandra Waldman, the visionary co-founder of Universal Standard, the world’s most size-inclusive brand (with sizes 00-40), interviewed each other in New York’s SoHo neighborhood the day before Valentine’s Day. The result? A captivating conversation—with moments of tough love—about the heart of fashion.

Alegra O’Hare: I’m going to ask you a question relative to the past, one relative to the present and then one for the future.

Alexandra Waldman: Oh, very interesting.

O’Hare: What is your biggest regret of the past?

Waldman: It’s surprising to me how quickly the answer came to my mind. I wish there had been that confluence of necessary ingredients—human, financial and otherwise—that would have allowed us to start [Universal Standard] three years earlier. It would have allowed for enough time to really learn at less than the break-neck speed that we had to do. What about you?

Cheril Sanchez

O’Hare: I wish earlier in my career I’d have accepted positions abroad—like across the globe and not a country next door. Earlier in my career I had that opportunity, and I think a mix of fear and insecurity [stopped me]. It would have really broadened my cultural knowledge, not just my professional knowledge.

Waldman: Legacy is a bit of an albatross around the neck of big, established brands. And because of the amount of people who are contributing to any decision, and where they are in their lives compared to the cultural movements that are affecting the brand, it can be difficult to expect meaningful change. You’ve been at the helm of some of the most iconic global brands. What do you think needs to happen within big legacy brands in order to turn things around and make their contribution relevant?

O’Hare: The longer the legacy of a company, in my experience, the harder it is to turn the ship because it’s a mix of doing things the traditional way and staying in the comfort zone. It’s also about employees, because in large companies people have been there a long time, and it’s human nature to get used to ways of working. I think [the answer] is shifting the attention on the consumer. And the other one is data, to really help you form your decisions and bring the rest of the organization on board. Also, watch the competition, but don’t benchmark them. A recipe for disaster is when you’ve got emails saying, “Look what they’re doing.”

So I’m going from past to present: What is a saying that you’re known for repeating?

Waldman: “Bite off more than you can chew—and chew it.” I also personally believe that it’s much easier to be right than it is to be kind. There is this tendency for people to throw facts out without taking into consideration the effects. I think there are ways to collaborate with people that are more emotionally productive.

What about you? I’m curious to know.

O’Hare: “Do something that scares you every day.” It doesn’t mean jumping out of an airplane. It could be that one phone call you don’t want to make to that one person that is really annoying and you could just send an email. But you know you should call them.

Another one is—I don’t know if this will get published but—”Shit floats.” Sooner or later, things bubble up, so it’s important to hit conversations right away. That’s something that I learned over time, whether it’s employees that haven’t performed or conflict situations.

Waldman: My business partner and I promised each other that we would always nip any issue in the bud before it had a chance to take root.

Do you think culture has always played this big of a role in brand marketing, or do you feel that it’s become more necessary and potent? There’s so much happening in the world right now from sociopolitical perspectives; it’s making people choose sides and it’s making them declare themselves, and that is building a culture of extreme honesty or extreme revelation.

O’Hare: It’s always been there, but I think technology and innovation unleashed it. Now, thanks to social media, you’re able to voice your opinion and to voice your opinion collectively. So culture has become even more important because now you feel part of a community that shares that same belief. I think culture definitely is at the forefront of every successful brand going forward, regardless of the industry you’re working in.

Waldman: Do you think it’s made companies more or less risk averse?

O’Hare: It probably depends on the company. Some companies now are overly cautious because everything is so sensitive. You print something on a T-shirt, and then all of a sudden everybody goes wild. Now they’ve got the department of diversity and inclusion and things that did not even exist in a lot of companies. So this overly cautious [mindset] has also brought some good things, but from a creativity point of view I’m not so sure if that’s having a positive effect or not.

Waldman: To me, it feels like you’re in a constant state of choosing between being criticized and being irrelevant. With legacy brands in particular there is a tendency to either water things down beyond any meaningful message or really just run into a mistake that then needs to have crisis management. It doesn’t have to be one or the other, but I do think that you have to take a stand and be willing to say, “This is what we were actually, really saying.”

O’Hare: Then you’ve got decisions by committee, and everybody wants to please everybody else around the table. Maybe you did have that great idea, but then it just goes through this whole process.

Waldman: Yeah, it goes through the wringer and then it comes out completely blanched and anemic.

O’Hare: I’ll think about the Kendall Jenner Pepsi ad, and I think, “Was that the original idea, or was the idea different and then it went through a wringer?”

Waldman: This is why younger, newer brands [have an advantage], because they don’t have that top-heavy accountability to the big boards and the big meetings and the big people who have been there for 23 years and aren’t capable of changing their minds or generating completely original ideas. I think that is why the newness and fearlessness is coming from younger brands who still own themselves and can take those risks.

O’Hare: I totally agree. I think you’re a pioneer for the fashion industry—somebody who sees where we’re going. My third question is about the future. Where do you see the culture of fashion in general evolving to?

This story first appeared in the March 2, 2020, issue of Brandweek magazine. Click here to subscribe.

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