This week’s article is by request. A friend of mine works in a law office in downtown Toronto and loves her job, except for one thing: her office has casual Fridays. This friend has great personal style, so that’s not the issue. Her problem is not knowing how much to dress down – how casual is too casual on “casual Fridays”? This is a difficult question to answer, mostly because every workplace is different. How we present ourselves and dress influences how we’re perceived, and this is especially true in a professional workplace. In fact, 24% of women factor an office’s dress code into their job choices. But, what do you wear when that office has a day with loose clothing guidelines?

Casual dress-days began in Hawaiian workplaces in the 1940s when some Honolulu businesses allowed their employers to wear Aloha shirts at certain times, becoming Aloha Friday. Thirty years after it began in Hawaii, there was a surge in the production of cheap clothing outside of North America while a new generation, with more relaxed opinions about professional clothing, entered the workforce. This combination resulted in a demand for a casual-dress workday for workers. Casual Fridays spread throughout the United States and Canada over the next few decades, becoming widely accepted in the early 1990s. More recently, casual Fridays are becoming common practice in parts of Europe.

In the 1990s, Dockers used the popularity of casual Fridays to market the perfect casual workplace look for men: khakis and a button-up or polo. Some workplaces even received a Guide to Casual Businesswear for men, which basically acted as a giant, informative Dockers advertisement. However, women weren’t fortunate enough to receive a manual. The main rule to keep in mind for casual Friday (for men and women): dress how you want to be perceived. It’s not like everyone disregards how you come in on Fridays, or that the Friday workplace rule that you cannot look at others’ clothing. If you want your colleagues to think of you as a teen punk whose top priorities don’t involve professionalism, then go to work in your Backstreet Boys t-shirt and ripped skinny jeans. Otherwise, keep it business casual (key word: business).

For women, there are some basic dos and don’ts for casual Fridays. Do not wear anything too revealing, too tight or too wild. Do opt for a more casual blouse or top. Think something you’d wear to meet your partner’s parents. You can wear something slightly tighter or with shorter sleeves, but while remaining professional. In some more professional workplaces, it is considered taboo for women to fully bear arms. If that’s the case for your workplace, that rule continues on casual Fridays. If you do go sleeveless, bring a light cardigan or blazer to cover up for meetings. For pants, casual dress pants are always appropriate. If you were hoping to be a bit more adventurous, you could show a bit of style with a more trendy pant, or show some skin in a pair of shorts or a skirt. Remember that rule from camp where skirts and shorts had to be below your fingertips? That’s too short for a professional businessplace. Keep your shorts and skirts to your knee. Although you can wear patterns and designs more comfortably on casual Fridays, keep crazy and bold patterns for the weekend. If your workplace allows jeans on casual Fridays, your denim should be darker, a comfortable fit and straight legged or boot cut. Never wear jeans on your first casual Friday. If more than a few people are comfortable wearing jeans on Fridays, then you should be safe. As for shoes, it depends on what you wear. Shoes should not leave the realm of professional, flip flops and platform pumps do not fall into that area. Nice sandals work if you’re wearing a skirt, but flats and professional heels are always guaranteed. Casual Fridays are the time when your style can relax a bit, so some bolder accessories (such as chunky jewellery or an oversized watch) are appropriate if balanced with a plainer outfit. Remember, though, that the office is no place for hats.

For men, there are easier guidelines for casual Friday. A button up and trousers or khakis is perfect. If your office is more casual, a polo is also appropriate. If you do wear jeans, keep it dark, form-fitting but comfortably loose. Avoid slouchy denim with no shape. Shorts should, again, be to the knee. As for women, men can also dress up these outfits with statement accessories, such as an original watch or humorous cufflinks.

For both men and women, any sort of activewear or sweatpants/sweatshirts are not appropriate. Keep the rest of your appearance neat and professional (hair managed, makeup neat). Many workplaces’ employee handbooks set out guidelines of what is expected for casual Fridays in the workplace, so do your research. Otherwise, try to check what your bosses and colleagues wear to figure out what your workplace’s acceptable styles are. Also remember to dress for your day. For example, if you have clients coming in or a meeting, jeans are not appropriate. Like anything in fashion, you have to figure out how to incorporate your own personal style into business clothing.  If ever in doubt, just dress like it’s a Monday.

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This piece was written by Rebecca MacDonald, Fashion Columnist at Rhetoric Magazine. Come back for more every Thursday!