About Us



About The Company

“Where can I buy men’s dress shoes that fit small feet?”

Here at Tomboy Toes we believe that the clothes you wear should make you feel great, should fill you with confidence and fit your body as well as fitting your ideal sense of self. When you invest in really nice shoes, those shoes should suit you and your style - regardless of the size of your feet.

The idea for the company first began to formulate in the mind of its founder, Benjamin Craig, when he was out shoe shopping for an important job interview. He was moving up in the business world and wanted to treat himself to some really nice shoes that would give him that extra hit of moxy for the big interview.

The only problem? As a 5'4" trans guy, the shoes he wanted - men's oxfords or derby style dress shoes - didn't come in sizes small enough to fit him, and the shoes from the women's section that did fit didn't have the style he was looking for. He spent four hours desperately searching through the mall looking for a shoe store to give a couple hundred dollars to for some high quality oxford shoes that would fit smaller feet.

He looked for men’s shoes in small sizes, women’s shoes in men’s styles, heck, he even held out hope he might find a pair of formal boy’s shoes that would fit him. It wasn’t to be - and this certainly wasn’t the first time he'd found himself frustrated searching for a product that both fit his body and matched his sense of style.

Knowing he couldn’t possibly be alone, Benjamin pondered his frustrating inability to find masculine dress shoes that would fit a trans guy with smaller feet. He ended up settling for a pair of shoes that were kind of what he wanted, but not really. It was an issue that had trailed him for as long as he’d been buying his own clothes - even before realizing he was trans, it had never been as simple as he wanted to clothing shop, since he preferred men’s fashion and could never find anything in the right size.

Tomboy Toes is the solution. Starting with the humble ambition to give well-dressed folks with smaller feet access to men’s styles of dress shoes in smaller than normal sizes, Benjamin sought out a supplier that could do several of their oxford derby style shoes in "women’s" sizes. After some rigorous testing and ordering of many pairs of sample shoes, he selected his launch lineup, pulled together his branding and website, and thus Tomboy Toes was born!

The company’s mission is to make sure women, trans men, nonbinary people and anybody else with smaller feet never again have to settle for shoes that are only kind of what they want. You deserve better.


About The Founder

“Who are the people behind Tomboy Toes?”

Benjamin Murray Craig is a queer transgender entrepreneur from Toronto who graduated from Trent University with an English and Cultural Studies joint major in 2011, worked as a Product Marketing Manager for a couple different technology companies, was brought on to a small, intense Canadian startup in 2015 as Senior Marketing Manager, and then in 2016, having learned immense amounts, decided to launch his own e-commerce venture.

Benjamin has always had a deep fondness for outfits that make him feel like a secret service agent. His current passions include roller derby, video games, writing, reading, kung fu, and his two calico cats Lycaon and Leo. In addition to running Tomboy Toes, Benjamin is a professional prop and puppet builder for film and television, and when he's not ordering shoes and managing inventory, he's usually up to his elbows in paint and prop foam.

Ben's personal philosophy is that while confidence comes from within, a major source of that inner strength is whether your outward presentation makes you feel awesome. He's a strong advocate of buying things you catch yourself wishing you could pull off - you don't need to earn the right to wear those clothes. You're already worthy of them. Just go for it!