We spoke to Cyndi Lauper about her new shoe line, Pride parade + more

Cyndi Lauper: she of the many-layered crinolines and pioneer of the undercut, has come a long way since “Girls Just Want to Have Fun.” Since her heyday as a cheeky ‘80s pop star, she’s been inducted into the Songwriter’s Hall of Fame, appeared on Donald Trump’s Celebrity Apprentice, and given a speech to the U.S. senate on LGBTQ homelessness. Her latest venture is partnering with the social entrepreneurship company, Make A Difference Every Day (M4D3) on a shoe collection that will benefit Cyndi’s charity, the True Colors Fund.

Read on to hear Cyndi Lauper’s take on painful footwear, her respect for Donald Trump, and Joni Mitchell drag queens.

So you’re launching the M4D3 collection and you also wrote most of the music and lyrics for the musical Kinky Boots. Do you have a favourite pair of shoes?
CL: I have a pair of Michael Kors wedges that have slats. I also like the new sandals I got because they’re comfortable. Some shoes kill your feet, but those are comfy. These don’t kill your feet either. (Cyndi points at her shoes. She’s wearing a precarious pair of six-inch red wedges with a talon-like heel.)

That’s incredible. Do you have a favourite shoe designer that you’re obsessed with?
I love Miuccia. She’s made some good ones that I like. Miu Miu, Prada. Manolo of course, you always have to go back to that. As I get on in life, I feel that some men who design shoes that really hurt should be forced to wear them for 8 hours, and then come back to the drawing board.

The shoes in the M4D3 collection look super comfortable. How did the collaboration between M4D3 and True Colours come about?
We were looking to sell something to help the [True Colors] fund. Everybody else sells vitamin water or something. I don’t know anything about vitamin water, but I do like shoes. So I think it was through Lisa [Barbaris, Cyndi’s manager]. All of a sudden they were showing me prototypes. I was like, “Can you switch this?” I thought it was cool. They’re a walking shoe. People should walk.

Were you involved in the designing?
Yeah. I said, “I want a shoe I would actually wear.” But you can’t go too crazy because you want them to be successful. You have to ask, “What’s going to be the most successful shoe?” Because you want to make money for True Colors. I like that denim sneaker, that’s my favourite.

Do you ever wear sneakers?
Yes, of course I do. The kind of sneakers I wear for walking are two sizes too big and they’re men’s shoes, so they look a little clown-y. My toes are long and everything always squashes my feet.

In the ’80s, you were known for your wacky, awesome style. Would you say that your style has changed over time?
I think I’m very demure now. (Note: Cyndi has bright pink hair and is wearing a punk-inspired plaid blazer, leather skinny pants, and the aforementioned talon shoes.) I do not want to look conservative, in any way, shape, or form. But I think I look very demure.

You were one of the international grand marshals of the Pride parade that happened in Toronto last year…
I [was]! I [went] as Marie Antoinette in her underwear.

Have you ever seen any Cyndi Lauper drag queens?
No, I haven’t actually. I’m not big like Tina Turner. There are a lot of Tina Turner drag queens. I did see a Joni Mitchell one once. They played dulcimer too. I almost died.

You’ve always been outspoken, whether it’s “Girls Just Want to Have Fun” or advocating for homeless queer youth. What inspired you to start the True Colors fund?
There was a need. [It’s estimated that 40% of homeless youth are LGBT.] Lisa and I were doing the True Colors tour, and at the end of the tour we realized that we just couldn’t leave everybody hanging. So we did the fund, and the kickoff for the fund was going on the Donald Trump show. That was a trip. That’s one good thing Donald Trump did. He supported the LGBT community by having me on and we won some money that we put towards the True Colors Fund.

What would you say has been the highlight of your career?
Winning the Tony, working with Harvey [Fierstein], that was a big thing. The Songwriter’s Hall of Fame. That was big because I always had to fight to get my own songs on my own album. So it was a big deal for them to recognize me as a songwriter. I don’t know if they recognized me as a songwriter because I won the Tony [for Best Original Score]. I was the first woman to win it. But who cares.

I know that Canada has a special place in your heart, and you spent some time here hitchhiking in your early 20s. Can you tell me a little more about that?
I was lucky. It was a fortunate time. I’m still alive. I wouldn’t recommend it for kids to go do it now, because it’s a different time. But I went to Canada to do a tree study with my dog. I went to find myself, to prove that I could do something. And after that I wound up moving to Vermont, which is not far from Canada. But the people here were always very kind to me. I wanted to become a resident, but I didn’t have anything and I didn’t know what the heck I was going to be.

Where is your favourite place that you’ve ever travelled?
Well I just came back from the south of France. That was pretty damn great. You’re going to think I’m so lame, but I always go back to New York. There’s no place like home.

Is there one thing you’d like to do that you haven’t done yet?
I would like to take a little trip with my son, just me and my son. I haven’t been able to do that yet. But we’ll see.