Founder Spotlight With Benjamin Craig, Tomboy Toes
Photo Credit: Tomboy Toes
Benjamin Murray Craig is the Founder of Tomboy Toes, a footwear brand dedicated to creating men's dress shoes for trans men, nonbinary folks, women, and anyone with smaller feet. His inspiration stemmed from searching for formal shoes before a crucial job interview and not being able to find a pair he liked in his size. This is how Tomboy Toes was born, ensuring no one has to compromise their style due to limited options designed around gender constructs. Today, the brand offers a range of formal and semi-formal shoes and boots crafted from vegan and genuine leather in various, inclusive sizes.
One of the things that stands out most about our interview with Benjamin is how much he truly embodies the spirit of entrepreneurship. The most compelling characteristic is his resourcefulness. Benjamin was able to leverage transferable skills he taught himself while working for a startup and use those to get Tomboy Toes up and running. From sourcing a manufacturer to designing the shoes, Benjamin utilized his research skills and inspiration to get the business off the ground. It’s a true testament to the do-what-it-takes mentality that entrepreneurs must have.
Ben’s story is a remarkable example of turning a personal challenge into a thriving business that caters to an underserved market, reflecting his deep understanding of and commitment to his community. Check out the interview below!
What was the inspiration behind Tomboy Toes and how did you get started?
The original seed of the idea was planted in my mind one long afternoon at the mall during a fruitless search for new shoes before a job interview. I spent about three hours going from store to store looking for handsome, masculine dress shoes that would fit my women’s size seven feet and getting nowhere. Not only did none of the stores offer what I was looking for, it felt like scaling a mountain every time I had to work up the courage to ask a sales clerk, as if there were something shameful about being a woman looking for “men’s” shoes, which was what I believed myself to be at the time. Spoiler alert: I realized nearly half a decade after starting Tomboy Toes that I was a closeted trans man. Not to say there aren’t loads of women who want to wear and look fantastic in traditionally masculine shoes!
Of course, I didn’t just start the company then and there. That happened months later, after I’d gotten the job and had been working for this small, fast-paced e-commerce company where I was thrown into the deep end and tasked with learning how to source, market and host a website for products that were being sold online. To keep up with the intense pace of the job and the sheer amount I needed to learn in such a short time, I started listening to e-commerce podcasts like Shopify Masters and more on my commute to work every day. Then I had this lightbulb moment where I felt sure I could do this for myself, too. The frustration I’d felt around not being able to find those shoes bubbled up to the surface of my mind. If the product I was looking for didn’t exist, why shouldn’t I make it exist?
I threw myself into the idea, coming home from work and spending up to four hours each night researching manufacturers, ordering samples, designing logos, coding the website, reaching out to photographers, and writing marketing copy. I started working on the project at the end of March 2016 and by the end of that April, the company launched. My first sale ever was to a friend of my mother’s (whom I’ve never met) after she shared the link on her Facebook page. Thanks, Mom!
What does your creative process look like when working on a new product, brand, or campaign?
I usually play Hamilton on repeat and let my passion take over, immersing myself in the task ahead of me. I’m a big fan of to-do lists as a way to feel like I’m making progress, maintaining momentum, and figuring out priorities.
Before I create a new product, I think about what I personally wish already existed. Our best selling shoes are the simple, clean, classic ones that are hard to find in smaller sizes. They’re the kinds of shoes I watched my dad put on in the morning on his way to the office and dreamed of owning someday. Likewise, the latest product line we launched is the Traveler’s Toecaps, which are a lightweight wool and vegan leather dress boot design inspired by a pair of boots a friend of mine owned that I absolutely adored. He sent me to the brand’s website and none of them came anywhere close to my size. And, as is typical of shoe brands, if you try the women’s section, the styles are completely different. So I made my own!
Also, in the final quarter of 2023, we started experimenting with customer-driven product rollout. I always collect information based on the comments people leave about what shoes we don’t carry that they wish we had. On top of that, now I’m sending out polls via email and social media showing possible new color variants in different patterns. Then the option with the most votes will be the style we release next! With our first poll, I was really excited about the winner — it’s a version of the Traveler boots in a very bold faux-embroidered peacock pattern.
Photo Credit: Tomboy Toes
What is one challenge you have faced as the Founders of Tomboy Toes and how did you navigate it?
Truly the biggest challenge Tomboy Toes has faced was the COVID-19 pandemic. It was a huge hit to our sales. Luckily, we were able to weather the storm and keep all employees and contractors on, but it was only possible because I was in a position of privilege where I had savings I could fall back on. I know many small businesses had to shut down in 2020, and I’m very fortunate that Tomboy Toes wasn’t one of them.
What is your long-term vision for Tomboy Toes?
I’m really excited about the new Travelers because they have a combination of fabric and leather. There's a lot of opportunity there for experimentation and limited edition runs that’s harder to do with traditional all-leather shoes. Ultimately, I want to be able to keep expanding our offerings and keep listening to customers about what kinds of shoes they want. I think it would be awesome to offer more casual shoes as well. That’s another area where I struggle to find shoes that suit my style and fit my feet. Sometimes it feels impossible to find a nice pair of adult-looking sneakers in my size that don’t have some kind of feminine color scheme.
If you could give one piece of advice to future LGBTQ+ entrepreneurs, what would it be?
Listen to business and startup podcasts, and absorb as much information as you can.
“Be prepared to do every part of the business and don’t be afraid to learn things you think you’re not capable of.”
I don’t have any kind of formal background in fashion or finance or accounting, but I know how to Google stuff I don’t understand, and I’m willing to overcome my fear of failure by just being curious. Ask yourself the question: If I did go for it, what would it take?” and then write down a really detailed answer for yourself, with tangible steps. Do the research, and don’t shy away from numbers.
What LGBTQ+ owned brands are your go-to's and why?
Immediately I want to give a shout-out to Toni Marlow. I’ve had the pleasure of meeting the Founder, Jalisa, for coffee and some fantastic conversations about strategy as a queer bootstrapped business owner more than once and I always come away from feeling energized and optimistic. Toni Marlow sells comfortable, high-quality undergarments and hit the market originally with boxer briefs made to easily hold menstrual pads. They have a mission of raising $1,000,000 towards suicide prevention, which I think is incredible.
Photo Credit: Tomboy Toes
Tell us about one of your values and how you have incorporated it into your brand.
Visibly queer folks statistically have lower disposable income when next to comparable groups of cisgender, heterosexual peers. Subconscious or outright discriminatory hiring practices and opportunities for promotions, as well as a higher likelihood of being refused financial support by homophobic or transphobic parents, means that this is a demographic that has less spending money through no fault of their own. When I started the company, I wanted to make sure I was offering these shoes for as low of a price point as I could justify while still keeping the company in business. There are other shoe brands out there selling similar products for three, sometimes four times the price, but I’ve kept my margin as thin as possible to try to ensure as many queer people as possible could have access to affirming, confidence-boosting footwear as they navigate the world. That philosophy has driven choices like offering a lot of vegan leather options. Vegan leather can last as long as genuine leather if cared for correctly and is a significantly lower price point for us to source, which means we can sell it at a much lower retail price to the end customer.
How do you take care of yourself, especially during this moment in history (a record number of anti-LGBTQ+ bills being passed / an increase in violence against our community)?
There’s a tricky balance between doing what you can to make a difference and not inundating yourself with misery, and sucking yourself dry of hope and energy, and replacing it all with anger and despair. One of the ways I stay sane is by limiting how much news I consume and avoiding looking at headlines first thing in the morning when I wake up. On the other hand, one of the ways I stay connected and hopeful is by giving what I can to overturn and fight back against anti-LGBTQ+ bills — in my case, money. Our Rainbow Multipack of shoelaces has been available to buy from the store since 2016, and every year we donate a portion of the proceeds to the ACLU to help fund and empower the people doing the work that I’m not in a position to do with my own two hands.
Who is your favorite LGBTQ+ celebrity and why?
I’ll admit to a certain personal kinship with Elliot Page. When I was twelve or so, my older cousin said that there was this one particular actor that reminded her of me, and she happened to be referring to Elliot Page. When he came out as a queer woman, it allowed me a convenient foothold to do the same. Then when he came out as a transgender man, within something like a month of me finally figuring out that I was trans, I couldn’t help but laugh at the gift of being able to use that same foothold. (“Remember how you said all those years ago that Elliot Page reminded you of me? So, funny coincidence about him just coming out as trans…!”)
Can you share one fun fact about yourself?
These days I’m a big Dungeons & Dragons nerd! I first learned to play back in my undergrad (shout out to Mike for somehow teaching a squad of 19-year-olds to play 3.5 edition DnD) and ran a campaign for my friends for several years. I reconnected with the hobby during the lockdowns and have been really enjoying it as a creative outlet and a way to weave stories with cool people.
