Cynthia Rowley has all the talents: Designer extraordinaire, fashionista, CFDA award-winner, author, adventurer and certified badass, to name but a few. Not that it needs explaining, but she is a household name– then, now, and always. She turned her business into a lifestyle brand beyond the realm of fashion. A global legend, we stole a drink with her in the city where it all began.

Is it true you were discovered on the L train here in Chicago? What do you remember about that day?

It’s so crazy. I remember that day like it was yesterday. I just remember everything about it. It’s the whole fake-it-till-you-make-it mentality. Isn’t that really the basis of everything? I say that I don’t like fakers– people who pretend to be something, or say they can do something that they can’t– but if you can deliver on that promise and it holds up… I think it’s all about determination and tenacity.

What train were you on and what was it that you were wearing?

I used to live on Pearson Street and my back door opened up to the McDonald’s parking lot on Chicago Avenue. There was an L [train] stop right there that I could take to the Art Institute and that’s how I would get to school every morning. I was wearing a khaki puffy-sleeve jacket that, actually, I should probably redo. I should probably redo that, reissue it. It’s kind of cool. This woman came up to me and said, “I love your jacket, where did you get it?” I was like, “It’s mine, I’m a designer,” which I was totally not. I didn’t know anything. It was like a school project. She was like, “Here’s my card. Bring it to my office on Monday with your collection.” I had no idea what she was even talking about. I went to school and asked everyone. I went to the fabric store – to Vogue Fabrics – that’s still around, right? I bought all this fabric, sowed five things and brought it to her office [at Marshall Field’s]. She was like, “Oh, that’s cute. What’s the style number on that one?” I said, “One.” And then she asked, “What’s the number on that one?” I said, “Two.” Then I confessed. I hear she’s now in the furniture business.

What did success look like to you when you first started?

Everything was about very minimal goals. If I had some lofty, riding-in-limos-with-supermodels goal, I would have constantly been disappointed for about ten years. My first goal was, at some point, to not be a bartender anymore, even though I did like it a lot. At some point I didn’t want to have to do that to pay my rent. That happened and then at some point I wanted to move to New York. I think those happened simultaneously. The rest is a blur. I remember thinking, “If I could ever get something in Women’s Wear Daily.” It’s the industry [trade magazine]. When that happened, it was enough to keep me going and then the next little thing was enough to keep me going. Then each of those little goals gave me the impetus to reach forward.

Do you wish you could go back and tell your 20-year-old self anything?

I was just thinking about this. I would rather have my future self tell me what to do now than have my current self tell my 20-year-old self what I should have done.

Are you content with your success? 

No. It’s worse than ever. I don’t know what happened. People think it should get easier. Now I see even more opportunity. I see an even bigger world. Before, everything was just about getting done what was in front of you. Now, anything is possible. That’s what’s amazing about our time now. You can have an idea, you can get it made. It’s easy to find places that make stuff. You can take some pictures and put it up online. It’s so easy that it then creates this massive amount of opportunity. That creates the stress of, “Why aren’t I doing this and that?”

Did you ever feel like giving up along the way?

Yes, seriously, all the time. In the beginning it was all the time, because it’s really fucking hard. In the beginning nobody knows you. It’s just door slam after door slam. That’s why now I have a hard time saying, “No” to things. I say, “Yes” to everything, which I think is great, ultimately, and it’s sort of like that Warholian model that he perpetuated. It’s also a little bit dangerous and it’s only because everybody told me “No” for years. When people finally started to ask if I wanted to do something I said, “Yes!”

Is it true you started with $3,000?

Yes. I still have no partners and no debt. It’s still entrepreneurial. Everyone who works in the company is still entrepreneurial. Everyone is working hard. I always say, “They’re all doers.” There’s not a lot of hierarchy. Everyone works as a team. It’s fun. My greatest joy is to have an idea and be able to make it a reality, no matter what it is. I designed wine in little juice boxes when we were doing stuff for Target for [my brand], Swell, back in the day and I thought it was such a great idea –a juice box – but it was actually a little bit confusing. They were afraid that kids would drink it, which I of course never thought of. Actually, it’s not a failure but, today is April 20, and I’m not a big pothead, but I designed rolling papers because I thought I’d design something culturally relevant. I actually talked about it with my Vogue.com reviewer for the fall collection. I really think it’s a cool idea, but they got seized by customs last Friday. I was going to bring them here today– that’s what I was going to put in the goody-bag, but it’s okay. It’s on Well+Good today on how it can help your workout and help you relax and meditate.

What makes a great collaboration?

That’s a good question. I think it definitely has to be authentic. I think if people can see through you they smell that it’s not real or that you’re just slapping your name on something and you’re doing it just for the cash. It seems obvious. Now that we do so many things, it does increase the opportunities to partner with different people who are good at what they do. I know what I can do and then together it’s like magic.

Why is the Chicago creative community a great place to start? 

I feel like it’s a really nurturing community here. I have to say, if I would have started in New York, who knows? I could have had my enthusiasm stomped out of me. It’s a really enthusiastic, positive and nurturing culture here. People in Chicago want their own people to make it. Everyone supports everyone. Part of my thing with Lifeway Foods is that [CEO] Julie Smolyansky was from Chicago. She was the youngest CEO to take over a public company. To me I was like, “Yes, let’s do it!” You can take the girl out of Chicago, but you can’t take Chicago out of the girl.

I heard the idea to design a limited edition label for Lifeway Kefir’s spring hibiscus rhubarb pie flavor came together over drinks at a dinner party?

Oh there were drinks for sure. I was talking to someone recently about how it’s not like I go to my office and work then leave my office and that’s when my other life starts. That doesn’t exist. You socialize, you exercise – whatever you’re doing – and the ideas you generate work into that, work into your life, instead of being separated. Everybody needs a little down time. I go paddle out into the ocean and that’s my happy place, but then I do things the rest of the time. Last night I was at an event for the Public Art Fund and the person I was sitting with and I came up with 10 ideas for different books. You can’t really separate. I think it’s good. That’s what makes things authentic. You’re already living your life and if things cross your path and they work then you must be like-minded, you must have the same vision for life, the same inspirations.

You launched your first collection in 1988. Why do you think you were able to stay relevant over the years? 

I think, honestly, I’m truly and authentically excited about everything. I’m so psyched to go to Australia and have a big fashion show with my wetsuits and swimwear. That’s so exciting to me. I still feel so grateful. I’m so grateful that I get to do what I get to do. Everything is a huge gift. I’m like, “Yes, we have to do this.” We all work in a big space and sometimes you can hear my conversations and sometimes I’m like, “That’s amazing. That’s so fantastic. Thank you so much.” I hang up the phone and my employees say, “Now what do we have to do? Now what did you agree to?” We’re making surf wax, foam surfboards and all kinds of crazy tech accessories, fitness accessories.

Will you get to squeeze in any surfing while you’re in Australia for fashion week?

Oh my gosh, I’m so psyched. I’m only there… literally, this is how I roll… I landed an hour ago and came straight here and I have to leave by 7:30 p.m. to get to the airport again. Then I’m going to Australia. I think I’m only on the ground three days in Sydney. Do you surf? Right now I just went into a euphoric moment – almost a little teary-eyed – thinking about the ocean. I’m thinking about Malibu at the pier.

If you were going to have a party with your girlfriends what would you be doing? 

Aren’t we doing that right now? I am super easy and low-maintenance. We could literally be anywhere. I love the beach. I like a fun night, a big night, a New York night. A red carpet thing is always fun. Also, I’m good drinking on the beach with my buds any night. 

If you could have a drink with anyone, who would it be?

My grandfather designed a version of the PBR logo. I don’t want to promote underage drinking, but I grew up having a little sip, splitting a beer with my cousin. I hung out with him for a long time until I was in college, so I had a lot of good times with him. It would just be more time to hang out.

WE’RE CELEBRATING BOLD WOMEN WITH BIG IDEAS WITH SOFIA MINI IN CHICAGO.

READ ALL FEATURES HERE.

Sofia Mini is a single-serving of Francis Ford Coppola’s effervescent Sofia Blanc de Blancs, tasting of fresh juicy pears, summer melon and honeysuckle. A distinctive blend as unconventional as the woman who inspired it, Sofia Mini is for the impromptu, impetuous, live-passionately-for-the-moment kind of woman. The kind who lives like there is no tomorrow!

KIRSTEN MICCOLI PHOTOGRAPHY / A DRINK WITH AT CYNTHIA ROWLEY BUCKTOWN BOUTIQUE