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Men have it so easy at work – well, at least when it comes to knowing what to wear. For women, it's a challenge to juggle the right fit, the right tone and the right amount of comfort.

At the same time, there appears to be as shift in opinion about what is deemed to be professional attire. On a recent visit to my bank, for instance, my usual teller removed her cardigan, revealing several tattoos on her arms. I asked her whether management ever took issue with her ink and she replied, "Never."

Still, what you choose to wear to work can be fraught with difficulties, for employees and employers alike. Earlier this month, a woman employed by a temp agency in London was sent home without pay on her first day of work as an accounting firm's receptionist for wearing flat shoes, not heels.

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"I was expected to do a nine-hour shift on my feet escorting clients to meeting rooms. I said, 'I just won't be able to do that in heels,'" Nicola Thorp told the BBC.

According to the BBC, Ms. Thorp said she asked whether a man would be expected to do the same shift in heels, and was laughed at.

Now, Ms. Thorp has gathered more than 100,000 signatures for a petition to make it illegal to force women to wear high heels and makeup (which was also a requirement of the dress code), according to The Telegraph. The temp agency, Portico, has since changed its policy to allow flat shoes.

Ms. Thorp isn't the only one fighting back. In April, a Zara employee in Toronto quit and went public with her story after her managers insisted that she take out her box braids, saying they didn't meet the company's "clean, professional look." She is considering filing a complaint with the Ontario Human Rights Commission, according to the CBC.

Frankly, these changes to "acceptable" dress standards for women couldn't come soon enough. In a professional world where creativity, and out-of-the-box thinking is increasingly valued, why do we insist on a work force where black and grey remain the norm and women are forced to don expensive heels that aren't just bad for our feet, they break the second they get caught on a grate?

Companies keen to avoid the kind of negative publicity that Zara and Portico received should ensure they maintain a clear policy about what is and isn't acceptable to wear to work, Toronto-based employment lawyer Natalie MacDonald said.

"Employers may want to offer a range of options to both males and females in the workplace to avoid discriminatory behaviour," she added.

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Ms. MacDonald acknowledged that the issue gets trickier when there are unspoken rules about how to present yourself, for example, with respect to tattoos or boldly coloured hair.

"You don't want to be seen as an employer dictating how an employee puts himself or herself together physically, but you would expect an employee to come to work looking professional," she said.

Problem is, what if we can't agree on what constitutes "professional."

Andrea Sampson, who has held vice-president roles in advertising and marketing agencies, dyes her hair purple and said her locks have been "every colour and design" over the past 10 years.

"Having fun with my hair is a part of who I am," she said.

It wasn't always easy. Once, when she was vice-president of strategy for an advertising agency, she was asked by a human resources director to change her hair colour, saying it was unprofessional.

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Ms. Sampson replied that clients hire agency people for their creativity, and if they wanted to hire someone who looked and thought like them, they wouldn't be there. She refused to change her hair but didn't stay in the role for long, taking some clients with her.

Now, Ms. Sampson works as a professional speakers' coach whose clients include senior executives and is a founding partner at Talk Boutique, a speaker development and representation company in Toronto.

"I have presented to the presidents of banks, insurance companies and to major law firms. I often make a joke about being the only purple, pink or blue-haired women in the room and this usually opens up the conversation about the differences of creative thinking. I don't know if I have been eliminated because of my hair; however, I do know I have met and gained new clients because of a conversation that started about my hair," Ms. Sampson said.

So what should you do if you want to break out of the tired, corporate look? Ms. Sampson suggests that if you choose to express yourself through style, "own it and don't apologize for it."

"I remember early on when I started with crazy colours being nervous what people thought. However, I would always remember that I loved it, so it really didn't matter what anyone else thought. Other than that HR director and the very conservative owner of that company, everyone else always loved my hair."

Leah Eichler is founder and CEO of r/ally, a machine-learning, human capital search engine for enterprises. Twitter: @LeahEichler

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