Q&A: How to Dress for the Modern Office
Three real professionals share insight into how they approach dressing for work – and why it’s not as easy as it used to be.
The landscape of the contemporary workplace is constantly being redefined. Hybrid schedules, remote work, and collaborative workspaces have taken precedence over the traditional office environment, and consequently, traditional office dress codes.
No longer are most men required to wear a suit and tie Monday through Thursday (nobody ever passes up an opportunity to rock their favourite pair of jeans on Casual Fridays). However, where there’s a dearth of direction for what to wear, there's also a deepening chasm between professionalism and personal style.
So, what’s holding them back? In an ideal world, what would getting dressed in the morning look like?
We asked three real life professionals currently working in differing industries questions related to how they dress for their respective jobs. Leveraging the sage advice of Andy Chitty, Manager of Fashion Direction at Harry Rosen, we’ve offered our perspective on how they can maneuver through their sartorial struggles with dressing for the modern office.
Q. What's something you wish you could get away with wearing at work?
“Real estate private equity is still quite old-school, so tattoos are still somewhat taboo. I wish I could wear more casual attire like polos or T-shirts, especially on hot summer days or company golf events. With a full sleeve on one arm, I’ve refrained from doing so to avoid inadvertently revealing my ink. Nonetheless, the tats were still worth it.”
–Bobby Gosal, Real Estate Private Equity, Pure Industrial
“First of all, own your ink. Like your clothing, tattoos are a form of self-expression; they're a part of who you are,” says Chitty. “Displaying confidence in our choices is key to projecting authenticity and gaining trust in any scenario.”
Unfortunately, while it’ll be some time until tattoos are unanimously accepted in every industry, you shouldn’t use that as a reason to shy away from yours. Instead, try to strike a balance that honours both your personal style and the context of the occasion itself.
“A tattoo sleeve shouldn't feel any more aggressive than a full-out paisley printed dress shirt. Paired together, on the other hand, might be too much,” says Chitty. “Balance is crucial; tempering your tattoo with a solid, neutral-coloured knit polo or short-sleeve shirt will elevate your professional look while allowing your tattoo to be a meaningful part of the overall aesthetic without dominating the look.”
Q. What's your biggest frustration with dressing for work?
“Finding the right outfit in the rush of the morning that not only uplifts my mood and makes me feel upbeat and energetic but also looks presentable, professional, and not too stiff.”
–Armin Yousefi, Realtor, Sotheby’s International Realty Canada
Trying to balance professionalism with personality is a common wardrobe challenge, especially during hurried mornings, so preparation is paramount (and can be as simple as setting aside an outfit the night before). “Remember the three P’s: Plan, Prepare, Present,” says Chitty.
“Planning entails forecasting outfit choices in alignment with anticipated weather conditions and daily mobility, ensuring the selection of versatile and practical garments.
“Preparation involves meticulous care to guarantee the business-ready condition of garments – there’s nothing worse during a rushed morning than realizing your trousers need a good iron.
“Finally, Presentation emphasizes the importance of a wrinkle-free appearance, neatly tucked garments, and harmonious coordination—the result of the first two steps.”
Furthermore, investing in versatile wardrobe staples (like an unstructured navy sports jacket or refined deerskin leather sneakers or loafers) allows you to effortlessly mix and match comfortable items with ease while never compromising on elegance.
Q. How do you stay comfortable yet professional/polished at work?
“Finding that perfect balance is always a tricky one, especially working in advertising where there's an expectation we’re more on-trend and have more flare. It’s hard to beat the track pants and hoodie combo coming out of remote work, though I do love a nice blazer with a little something-something (like a checkered fabric) paired with staples like nice jeans and a T-shirt with a little edge (like a rock band logo). It’s funny, I seem to be comfortable taking more 'risks' with shoes and socks than other parts of my wardrobe.”
–Brent Choi, Partner & CEO, Angry Butterfly
The most important thing is it sounds like you’re having a lot of fun getting dressed already. In fact, your note about risk-taking with footwear and socks is a fundamental aspect of furthering one's own style journey. “Taking risks demonstrates that spark of style and forward expression that men, especially certain professionals, have been reticent about for a long time,” says Chitty.
Our advice? Keep taking risks and pushing the envelope with what you can and can’t get away with, especially considering you’re already in a field that allows room for creativity. Don't be afraid to switch things up and experiment with ways to wear a more formal shoe, like a loafer, with a more casual outfit up-top – perhaps those jeans and hoodies you referenced.
