Interview with Tomboy Toes: Masculine Dress Shoes for All Genders

A few years ago when we published a guide on types of masculine formal shoes along with vendors that sell them, there was still a serious dearth in options for a wide range of sizes. While there are still very few brands catering specifically to the dapperQ, a few solid companies have opened that are focusing on designing masculine shoes in smaller sizes.

Enter Tomboy Toes, a small e-commerce startup launched at the end of April 2016 that sells formal dress shoes in what are traditionally sold in “menswear” departments, made available in sizes intended to fit women, trans men, and non binary people with smaller feet. The company offers masculine oxfords and derbies in vegan leather. Tomboy Toes was founded by Lauren Craig, a queer woman living in Toronto with a background in technology and e-commerce startups, and is driven by a desire to make handsome, dashing shoes accessible to people who typically have a hard time finding what they want in retail stores.


I got the scoop on Tomboy Toes from Lauren to find out what inspires their designs, what makes them stand out, and what we can expect next.

dapperQ: Can you tell me a bit about the history and evolution of Tomboy Toes? What motivated you to start the brand?

Lauren: The notion for Tomboy Toes emerged organically from a problem I was facing myself: I had long envisioned a professional, impressive style for myself that incorporated the kinds of formal shoes that generally only existed on the “men’s” half of the shoe store. It was a years-long struggle, and it really came to a head when I was shoe shopping for an important job interview and decided to hit the mall with several hundred dollars ready to invest in a good pair of oxfords, spent six hours going from shoe store to shoe store, and came out with nothing. It was so frustrating, not just in the inability to find what I wanted, but also in how I had to overcome shame just to ask the salespeople if they had anything in my size, knowing there was a good chance I’d get dismissive treatment for my unusual request. I thought to myself, there’s got to be someone out there that caters to my demographic. What’s the solution?

The notion that maybe I could be the solution, that maybe I could start that company, nestled itself into my head like a little seed and grew steadily over the next couple of months. When one day the name of the company popped into my head, I knew I had to do it – I had the financial stability and enough time on the side to launch the company. I decided just to go for it. The company is totally bootstrapped, so a lot of the work – creating the website, writing the copy, crafting the ads, customer service, finding the right shoemaker – has just been something I did myself when I was able to. There was a lot of listening to pumped up music and powering through a massive to-do list that happened in the early days.

Since then things have taken off. When I place orders with my shoemakers these days I have to buy about three to four times the quantities I was ordering when I first started, and it’s a never-ending race to be able to offer more and more options for my customer base. People have really responded well and I’m constantly appreciative of the kind of customers I’m lucky enough to have.


dapperQ: How would you describe the Tomboy Toes aesthetic?

Lauren: That’s probably a question better asked of Stephanie Ash-Perry, the extremely talented stylist behind the Tomboy Toes photoshoots. When she and I were first working together to select outfits and locations for the photoshoots, I had all these big, theatrical ideas of the tone I wanted to set with these shoes. I was throwing around things like “fifties mob boss” and “the President with his feet on his desk” and “secret agent at a casino” and – well, you get the idea. Steph got to the core of what I was asking for and trimmed away the excess absurdity, rooting the aesthetic of our photoshoots in something closer to reality, and something more relatable to our customer base.

Thanks in large part to the sensibilities of Steph’s work on the photoshoot, our aesthetic is about that balance between formality and the potential for playfulness. Tomboy Toes is about an outdoor wedding in summer – it’s a date night on the boardwalk – it’s a powerful presentation in a boardroom meeting. With the ability to be semi-casual, but with aspirations of more. Youthful but ambitious, classic but modern. These are shoes that work with jeans and a sweater vest just as much as they work with a full suit.

dapperQ: What inspires your designs?

Lauren: Much of what we offer in styles is driven by my own personal sense of style. It’s a balance of sensible and clean styles with a powerful, classy sense of refinement that we’re going for. Some of the shoes speak to the kind of handsome brogues I watched my father put on in the morning on his way to work, freshly shaven and dressed sharp for an important meeting. Others say more about my secret aspirations to look like James Bond, sleek and elegant and perhaps a little dangerous. Ultimately, we try not to go too outside the box. We want to offer the classic, essential “men’s” shoe, but make it available in sizes that are gender neutral.


dapperQ: Many of our readers have problems finding masculine shoes that fit them properly. How is Tomboy Toes addressing this issue?

Lauren: When I first launched my company, I did research into what the most common women’s shoe sizes in North America are, and made that my initial focus. With a company that was funded on my own savings, I couldn’t have a massive inventory right out of the gate. As the company has grown and more capital has become available, we’ve invested that right back into making a wider and wider range of sizes available. The emphasis has been on going smaller and smaller, as those are sizes that people have a harder time finding in stores. When we started, our smallest size available was 38. We’ve just started selling our Downtown Dappers in size 36, and hope to have a new line of brogues available in size 36 by December 2016. Our ambition is to eventually be able to offer alternate widths, as well, but that’s going to be a question for 2017.

Because buying clothing online can be a little terrifying, we guarantee the fit of the shoes and have a pretty straightforward process for exchanges if they arrive and don’t quite fit right. We want every customer to have the best possible fitting shoes, after all.

dapperQ: How does Tomboy Toes stand out from some of the other recent queer clothing collections that have launched over the last few years?

Lauren: One of the most important things to me is accessibility, and a big part of that is price. It was really important to me to be able to offer shoes that were under a hundred dollars a pair. It’s not a coincidence that a lot of queer people, especially visibly queer-coded people, don’t have a lot of disposable income. When you look at other companies in the same space as Tomboy Toes, there are some really nice shoes out there available in gender neutral sizing, but none under the hundred dollar price point. I wanted to change that.

Another differentiator is that our lines are all available in a vegan leather alternative to genuine leather. We know there are a lot of people in our customer base who care deeply about purchasing clothing made without animal products. We’re fortunate that we were able to find a shoemaker to work with who was able to accommodate that in a way that doesn’t compromise the appearance and quality of the shoes.

dapperQ: How would you describe your personal everyday style?

Lauren: My day job is at a laid-back startup, so in my day to day I get away with a lot of plaid button ups and blue jeans. Lately I’ve started to accessorize a little more, but just in small flourishes. A simple metal ring, a nice watch, that’s about all I need. This time of year is when I get to bust out my leather jacket, which I will admit puts no small amount of strut in my step.

In my spare time, I have the pleasure of bench managing for a local roller derby team – on important game days, I go the whole nine yards with a three piece suit and the Tomboy Toes Roguish Brogues… naturally with red laces added, in homage to the team colors. I love the opportunity to be dressed to the nines and I have a particular weakness for vests. I’m working on expanding my range of neckties as well, because obviously the more of them I own, the better.


dapperQ: Has it been a journey defining your own personal style? Tell me about it.

Lauren: It has definitely been a journey. I didn’t think about it as much when I was a kid, even though I already knew I liked stuff from the boy’s section more. For a long, long time, I kept myself in oversized t-shirts and sweatshirts and just refused to think about it. The evolution to where I am now came in bursts. A haircut here, an item of clothing there, all slowly nudging me closer to expressing myself more honestly and fearlessly.

I’m sure there are lots of people who would say the same thing, but for me I was really freed by a bad breakup in my early twenties. I got out of this relationship and decided to ‘reinvent’ myself – aka start being the person I had always wanted to be, but was afraid to be because of my fear of disapproval.

I had one of those “aha” moments after that breakup when I was walking down the street and saw a woman go by who I just thought was overwhelmingly bad-ass looking. I thought, wow, I wish I were as cool as her. Look at her leather jacket! Look at her hair cut! Look at her amazing tattoos! Look at her awesome shoes! And then it hit me. There was literally nothing stopping me from having those things but my own fear that I wasn’t “worthy” of them.

I had unconsciously been telling myself that I couldn’t possibly have the look I wanted because I just wasn’t cool enough. Realizing how completely ridiculous that was and actually believing that if I wanted to be someone who wore those kinds of clothes I could just go out and buy them and wear them… I mean, it was a big deal! It was a huge revelation for me. That was when I stopped doing these timid, halfway attempts at wearing what I wanted, and just going for it fearlessly and shamelessly. Get that haircut. Buy those shoes. If you like it, you’re allowed to wear it.

dapperQ: Who or what has most influenced your personal style?

It’s hard to pinpoint any particular influence – I get these ideas in my head of the look I’m going for or the particular items I wish I had in my wardrobe, without being really sure of where I first saw it or how it lodged itself into my imagination. I’m a bit of a romantic at heart, so it would probably be an array of fictional characters that I look up to or wish that I had the presence of. Sometimes it hits me after the fact – that the shirt I fell in love with at the store looks just like an outfit worn by a character in a comic or on a show, or links back to some obscure thing from my childhood like Mr. Toad’s red waistcoat.

dapperQ: Who are your fashion icons?

What’s funny is, I’ve spent my entire life telling myself and telling other people that I’m not fashionable and I never will be. I was one of those “I’m not like other girls” and “fashion is a dirty word” teenagers, and while I’ve matured quite a bit from that reductive point of view, I’ll admit that for me, this company isn’t about fashion so much as it is about self-confidence. I’ve immersed myself in what I need to know and I can tell you all sorts of things about the history of the spectator shoe and the difference between a true oxford and a derby oxford, but my intention was never to break into the fashion industry. I saw a problem that needed a solution, and I felt strongly enough about it that I decided to try to help be part of the solution.

I love seeing people who have embraced the styles that make them feel at home in their bodies, people who own that dapper, masculine of center aesthetic – that fills me with a lot of joy. Nothing makes me happier than encountering pictures of people wearing Tomboy Toes shoes as part of an outfit that clearly makes them feel like they have the world on a string. Is it too corny to say that my fashion icons are my own customers? Too late. I’m saying it. My fashion icons are the brave and gorgeous customers I have the good fortune of serving.


dapperQ: What is the one article of clothing you cannot live without?

Lauren: I have a dark blue metal watch that I received as a Christmas present from my parents a few years ago, and I never leave home without it. I’m guilty of wearing it even with outfits it doesn’t really match just because I’m so emotionally attached to it.

dapperQ: What can we expect next from Tomboy Toes?

Lauren: Sometime in late November we’ll be publishing our fall photoshoot, which will feature the Downtown Dappers which recently became available in a light brown color. I’m really excited to get to share that photography with our audience – fall may already be on its way out but I’m not done enjoying that autumn leaf aesthetic just yet.

We’re also hoping to launch a new line of brogue derbies in December. Stay tuned!

Follow Tomboy Toes on their website, Facebook, Instagram, Twitter, and Tumblr.

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1 Comment

  • Thank you so much! I just ordered a pair of tomboy toes shoes. I usually hate buying shoes bc I’m nonbinary and well…the “women’s” shoes that fit me are entirely flimsy and impractical. But after buying these shoes I feel excited not let down. I’m really glad I found your site, and some awesome shoes!

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