Skip to main content
office apparel

September unofficially marks the end of summer and as all the kids I know lament the start of another school year, I mourn the end of season for a different reason: the clothes.

Even if I harboured some hope that I could squeeze another couple of weeks out of my summer wardrobe, the weathered turned, as if on cue. Now all those lightweight summer items that met the criteria of being business appropriate and comfortable will languish in the closet until next June.

That daily question of what to wear, which infiltrates my brain before I even get out of bed, remains more complicated than you might think. Clothes define your personality but they also define your role and the image you want to project. We expect doctors to wear white lab coats and expect bankers to don conservative suits. These strict rules of business wear can feel suffocating. While many men may complain about the restrictive nature of ties, they likely haven't spent 10 hours in high heels. And don't get me started on nylon stockings, which seem like a cruel joke, especially when you are in a rush.

Apparently our frustration with clothes can be more than merely annoying – it can have an impact on our mental health. A recent poll showed that a majority of workers in the United Kingdom found that a suit or fitted dress contributes to stress and has an impact on productivity.

If you factor in the role of the media, deciding which type of clothing defines success can be even more challenging, especially for women. Consider the ink spilled about Yahoo Inc. chief executive officer Marissa Mayer's photo spread in Vogue. The message I draw from this brouhaha is that women are expected to look good – but not too good – and many find that the concept of a glamorous tech exec is outlandish. To make matters worse, New York Fashion Week started Thursday, highlighting clothes we should want but can't wear until next year, or at all, really, further fuelling a sense of fashion inadequacy.

So how do you navigate this dreaded middle season of hot and cold? Decisiveness is the key, says Toronto-based fashion stylist Rinat Samuel, who tells her clients to "let each season go and move forward."

"Don't make the mistake of keeping summer in your fall wardrobe and vice-versa. You will be in a rush one day and make a fashion mistake in an important meeting," she said.

Even if you embrace fall, despite sporadic summer temperatures, corporate dress-code norms are fluid and evolving, making it difficult to judge what is appropriate. Because clothes reflect your employer's image and reputation, consider your surroundings before splurging on a runway knock-off or an "Ironic Dork" T-shirt.

Erin Nadler, president of Better Styled Inc. in Toronto, suggests carefully observing the choices of your manager and colleagues before making any radical fashion decisions.

"When in doubt, business to business-casual are always a safe bet. You're always safe with a pair of slacks and a separate jacket. Dresses are a fabulous option, too, because they can be dressed up with a jacket or down with just a simple cardigan," she added.

Ms. Nadler has observed a slight leniency in the business world toward different fashion choices and more professionals are dressing with their customers in mind, not their managers, so that they appear more approachable. This poses a challenge to professionals who have worked in the same industry for years and never altered their style.

"Women who have been wearing a suit and working for 25-plus years can get into a style rut. … It's hard to get out of your comfort zone and try something new, but it's important to keep your wardrobe fresh and current," Ms. Nadler said.

While we may imagine the biggest fashion faux pas to be plunging necklines and too-short skirts, Ms. Nadler said ill-fitting clothing remains a common mistake. Other stylists focus on another detail easily overlooked – footwear.

"As much as you love your favourite pair of shoes, it's important to retire them before they look worn out," said Christine Carlton, co-founder of The September, a soon-to-launch Canadian online shopping site for designer shoes. "Nothing says more about your look than your shoes."

Wearing the appropriate footwear is key for Ms. Samuel as well; she cautions women against wearing dark-coloured hose with light-coloured shoes, or men wearing stylish shoes with white socks. "I am not the fashion police," she said, "but after having been a fashion stylist for 27 years, I would give you a ticket for this."

Leah Eichler is founder of r/ally, a mobile collaboration platform for enterprises. E-mail:

Report an error

Editorial code of conduct

Tickers mentioned in this story