“A wise man will make more opportunities than he finds.” 

― Francis BaconThe Essays

Think about the things you aspire your colleagues would say about you when you’re not there.  You would hope its things like “fearless”, “a leader not a follower”, “creative”, ”not afraid to push the envelope” and  “practices good hygiene”. 

Now think about all the things you could do to make people think this about you.  Landing the big account, successfully launching a new product, implementing the new process that several others before you weren’t able to, etc... Chances are opportunities like that come by once in a blue moon. 

How about an opportunity to show off your creative chops and stand out from the crowd on a weekly basis?  Yes, I’m talking about Casual Fridays.  Use your wardrobe as your vehicle to demonstrate your creativity, individuality and fearlessness.  Be bold and use the combination of fit, colour and emerging brands to show off how connected and edgy you are.

Usually in a corporate environment people show off how street savvy and hip they are through pop culture references and familiarity with social media or whatever it is millennials are perceived to be immersed in.  Think about how you cringed when “twerking” was force fit as a segue into a long ass PowerPoint presentation that, not surprisingly, had nothing to do with “twerking”.  Or when you have to fake applaud when your CEO drops “hashtag” anything as an acknowledgement of how “with it” they are.  Using this approach as opposed to your wardrobe is dangerous ground since you’ll always have some 20-somethings who tired of your clips and references 6 months ago.  Also, these 20-somethings also lack the tact and diplomacy to not pass judgement on how outdated your content is to other colleagues.

 This is also your chance to get known for something  that sets you apart from the others.  I mean, something other than your current claim to fame, the misunderstanding with your younger female colleague at the last open-bar holiday party.  Its called the last open-bar holiday party not because it was the most recent but because, thanks to you and your violations of several HR codes, open-bar holiday parties are no longer. 

To better understand how to start taking advantage of Casual Friday, here are some simple Do’s and Don’ts around understanding how colour, fit and brand selection can work for you:


  • A golf shirt isn’t revolutionary but sporting a more modern athletic fit and some vibrant colours will turn some heads.  Resorting to the one you’ve had in your closet for years will just make you like someone’s dad with the sleeves hanging below the elbows
  • Use layering to achieve a different look – a golf shirt by itself for some environments may be too casual but using a slim fitting cardigan as a layering piece allows you to add that bit of professionalism and client readiness when needed.  Plus, in the summertime the AC in the office is usually blasting, keeping a cardigan as a layering piece will most likely come in handy
  • A Henley top (no collars, buttons ¼ of the way down your front).   Depending on the culture of your office, a Henley makes a solid alternative to a golf or sport shirt.  As the weather gets chillier, a slimmer fitting Henley makes a great layering piece underneath and provides a different look than the traditional crew or V-neck people sport underneath
  • Invest in some bright or light coloured khakis or linen pants.  You can get creative with some plaid pants, just remember to go solid on top or else it comes across as too Mr. Furley  
  • Get some colour.  Still as uncomfortable going all the way like the way you were in Grade 10?  Get a brightly coloured belt, socks or shoelaces to ease into it.  Any why wouldn’t you?  Think that guy who tormented you in public school is going to show up at your job asking why you’re wearing your sister’s clothes?  Think about where he is now and splash that colour on with confidence
  • Wear a casual blazer with jeans and casual shoes as an option.  This look became the uniform for external consultants who adopted this look as a way of conveying the message, “look how different we are”, which worked until they all started doing it.  This could be something for later on down the road when you’re comfortable with colour and pattern mixing to put together something OEC (Office Eye Candy) worthy
  • You wouldn’t repeat what someone else says at a meeting for fear of being a follower and not having an independent thought.  Its all about establishing your identity and niche and bringing that perspective that no else is bringing.  You may get taken more seriously if your attire reflects a unique perspective.  So try to find some stores that are off the beaten path that not everyone else is aware of and shops at.  Chances are you’ll find some great one of a-kind pieces that aren’t experiencing overkill.  In our “Love Toronto” section on our site, you’ll find a handful of small stores that are selling some great under the radar brands that are not widely available
  • If you’re really gunshy, there are accessories you can use to show you’re really cut from a different cloth without immersing yourself in flowery shirts, pink pants and fedoras.  Think about that beaten up, black and boring wheelie you pull around.  Invest in a cooler version with some funky coloured stitching, bright wheels or a distinct looking handle.  It will be a conversation starter and you won’t have to worry about being taunted about wearing your sister’s clothes


  • Treat Casual Friday as a way to show which sports team you root for
  • Just add running shoes to your Monday to Thursday ensemble
  • Assume Casual Friday means Jeans Day.  Leave the Mom & Dad jeans for your Mom & Dad 
  • Bring Black and Greys to the dance.  That’s what Mondays to Thursdays and funerals are for
  • Try Graphic or T-shirts.  Leave them at home for cutting the lawn or going out to watch a playoff game (if you live in Toronto, regular season game)