Skateboarding in high heels would strike many of us as not just impractical, but also terrifying.

But for Lindsay Lovejoy, it’s part of her journey through skateboarding, of staying true to herself, and taking on the streets her way.
But there’s a lot more to her than just skateboarding in high heels. Lindsay Lovejoy’s strong style and determined love of skateboarding comes from her background as a fashion designer and tailor. Living in Barcelona since 2012, she’s spent on average one half of each year traveling – searching for materials and antiques – and the other half producing small collections for boutiques and customers, teaching English, and, of course, skateboarding.
That’s a lot to keep on top of. But what are you all about deep down?
Lindsay Lovejoy: That’s a big question. Let’s just say that I am someone that plays entirely by her own rules and wants to set that example in everything that I do. I don’t drink or take any drugs, I’m more of an observer when I go out and am much more aware of my surroundings. I kind of feel like a spy sometimes. And when it comes to skating, I feel the most free when I can wear whatever what I want, cruise wherever I want and grab on to whatever I can – I want to get momentum in the street. It’s the ultimate freedom!
Women skateboarding – what does that mean to you?
I love seeing female skaters kill it on the streets, whether they’re just cruising around the city or doing some sick lines. I don’t ever want girls to limit themselves in what they have to wear or how they have to skate just to be able to compete with guys. It’s so silly and unfortunately I feel like skating is turning into such an image competition. I’m always going to be skateboarding in high heels and dresses because that’s how I hold onto my freedom and it’s just who I am and how I have fun!
“So I ended up duct taping my kingpin back onto the truck when it broke and rode that board for a year or so.”
How did you get into skateboarding?
When I was a kid growing up in Ohio, I found an old Nolder board in my garage that barely rolled but I pushed it around until a friend of mine gave me my first board and we would cruise some crazy cemeteries and parking garages in the city. I didn’t know anything about boards at that time, so I ended up duct taping my kingpin back onto the truck when it broke and rode that board for a year or so. People thought I was insane!
When I first invested in my own deck I began skating a lot of downhills and anywhere I could catch a lot of speed. Speed skating for me then was, and still is now, the ultimate freedom. Feeling the grind of the wheels on the pavement and the wind hitting me was an amazing sensation.
What do you love about skateboarding today?
One of the nicest things about skating is that you can travel almost anywhere in the world and share it with anyone who wants to try! The freedom of taking my skateboard to all the places I travel really allows me to discover things in my own way, along with the burning need to keep grinding in the streets.

What issues have you faced in skateboarding?
After so many years of skating I luckily haven’t broken anything or had too many serious injuries. I have however gotten into a lot of trouble with the police for skating in “prohibited places” and people in cars that aren’t the biggest fans of skaters. I’ve literally had people come close to hitting me with their cars just for skating in the street. People are nuts!
Where do you think that attitude comes from?
I think many people’s perspective of skaters can be that they’re aggressive and self-righteous, but those are an individual’s traits that have nothing to do with skating.
How do you counter that?
I’m always super positive and silly when skating and sometimes people have a problem with that as silly as it sounds. I think some people would rather just see me skating in sneakers and pants, practicing tricks all day then grinding in the streets with my heels and dresses on.
Why skateboarding in high heels of all things? Isn’t it really difficult?
I’m not against sneakers or anything, I just have been skateboarding in heels since I was a kid. It’s just normal to me! Moving to Barcelona some years back and having a closer knit group of skaters influenced me to actually have a good pair of shoes to skate in especially since I wanted to get more into tricks, even though people aren’t used to seeing me skate that way.
“I think my average skate shoes have about a 7.5cm heel which is a good height before you’re actually skating on your toes.”
How big a pair of heels are we talking here?
I think my average skate shoes have about a 7.5cm heel which is a good height before you’re actually skating on your toes. Besides the heel, the most important thing is that the shoe is pretty tight around the foot. I normally grab a half size smaller just so my foot is super snug so I feel a real grip on the board.
What do you think the most interesting things happening in skateboarding today are?
I think one of the most interesting things happening in skateboarding right now is creativity! I love seeing people be completely innovative within skating and just getting back to having fun instead of just focusing on having perfect lines to film all the time.
I saw this video a few years ago of this guy skating in a suit, then he jumped onto a bicycle rack, wrapped his tie around the truck to flip it in the air and landed on it. It was awesome! Keeping an open mind when skating is so necessary for the world of skating to grow. I mean you can see little girls in princess costumes doing kickflips in India. I love it!
What’s next on your journey, Lindsay?
I’ve actually already begun part of my next journey, which was to skate and hitchhike around Thailand looking for traditional fabrics, some crafting supplies and learn as much Thai as possible.
Then what?
After Thailand I plan on crossing into Myanmar by motorcycle and visit as many tribes in the north that are still weaving intricate designs with beads and thread by hand. After a few months wandering around, I hope to return to Barcelona and begin working on my next collection along with getting back to the streets with some friends.
I hope we’ll see you skating in this collection?
Definitely! Actually this would be one of the first collections that I will actually present because normally I sell my pieces directly to clients of mine or to shops. Being able to present my collection to the public and share my stories about traveling on the road and sourcing materials is something I’m super nervous about, but at the same time very excited.
Good luck and keep pushing.
Photos: Roger Ferrero, Tyler O’Connor & Luc Prouzat

