Moments of distinction

In Toronto, where every board meeting, Michelin-starred client dinner, and TIFF red-carpet gala tells its own story, dressing for success is more than just style – it’s an art form that presents confidence, ambition, and leadership in every professional moment.

As the city’s professional class prepares for its spring flourish, seamlessly transitioning between business settings requires a tasteful mix of personal style and classic tailoring. But Toronto is a fast-growing and highly diverse city that is as distinctive in its varied social and business settings as it is demographically and culturally.

How can Toronto’s business professionals feel confident in their preparedness for each professional moment, and in always being dressed for success?

For a life well dressed

Enter Harry Rosen, Canada’s luxury menswear design and retail brand with over seven decades of experience curating the finest workwear essentials from formal to casual and ensuring every professional is impeccably dressed for success.

At its core, Harry Rosen stands for quality, curation, and a firm belief that a life well dressed is the only way to live it to the fullest.

As Canada’s most trusted menswear authority, Harry Rosen proudly introduces their TL Insider Style Advisor-in-Residence: Adam Gallo, Harry Rosen’s Senior Divisional Merchandise Leader of Tailoring, Luxury Collections, Footwear, & Accessories.

“After 20 years with the company, I’ve truly embraced the art of dressing well and it’s always a privilege to represent a renowned brand like Harry Rosen,” says Gallo. “Our team takes great pride in curating a collection that’s not only relevant and stylish, but also comprehensive enough to meet the diverse needs of our clients in every aspect of their lives.”

Your work, your week, your wardrobe

In an exclusive Q&A with TL Insider, Gallo unlocks the secrets to a versatile wardrobe that meets every Toronto moment.

“Gone are the days of formal sartorial rules; instead, Toronto professionals can suit up, dress down, try new things, and be bold,” says Gallo. “As long as the clothes fit right, they will fit your life any day of the week. That’s a life well dressed.”

Explore new office wear at Harry Rosen.

The Job Interview: Tailored Confidence

Q: What’s your advice for mastering the job interview, where potential meets the first impression?

A: Confidence and preparation are key. Your experience, knowledge, and expertise are all on you. But let’s focus on how you show up. While your outfit may vary depending on the industry, there’s one universal rule: always wear something that looks fresh and new. Next, ensure you’re wearing a second layer. Wearing just a shirt can leave you looking incomplete - if you’re unsure about color, navy is always a safe, stylish choice. If you’re wearing a suit, excellent! If you’re unsure, go more formal. A sport jacket, chore jacket, or cardigan will always complete a look. And remember, always be fully buttoned up. Exposing your arms or chest is a look best avoided.

Office Casual: Relaxed Professionalism

Q: How should you dress for the daily grind?

A: Consistency and confidence are key. Don’t dress up some days and get lazy on others. Every day, imagine you could run into the CEO, a top client, or your future life partner–even on Zoom! Consider how you’re representing both your personal brand and your company’s image. Don’t be afraid to set a high standard. You’ll find that those around you will start to raise their own standards as well. Pay close attention to the fit of your clothes and how they’re tailored. For example, the length of your shirt should rest at the base of your thumb, your jacket sleeves should reveal a bit of shirt cuff, and your pant hem should never be too long or gathered. These subtle details all contribute to the overall silhouette and sophistication of your outfit.

The Afterwork Scene: Effortless Refinement

Q: What’s your advice for a seamless transition from the office to the nightlife?

A: If you’re already wearing a sports jacket or overshirt – unstructured pieces with more comfort and versatility that bring you seamlessly from day to night –  great! Don’t be afraid to leave it on. Whether it’s a sports jacket, chore jacket, or even a sweater-jacket, always make sure you’ve got that extra layer. Honestly, this should be your formula for workwear too, because it makes the transition from work to play seamless. And don’t forget: Versatile footwear is key – choose from one of our eight must-have shoe styles for men.

A Day of Meetings: Subtle Versatility

Q: How should you prepare for a jam-packed day (or week) where meeting stacked appointments all over the city can wear on your outlook and your outfit?

A: First, invest in high-quality anchor pieces. Whether it’s a suit, a jacket, a great pair of cotton chinos, an outerwear item, or a well-crafted pair of shoes, you truly get what you pay for. These pieces set the foundation for your wardrobe. A tailored item can elevate any outfit, and it doesn’t always have to be a suit or a dressy sport jacket. It could be a beautifully tailored trouser, hemmed neatly at the ankle, paired with loafers, a fully buttoned fine-gauge polo, and topped with an overshirt or sweater. Or perhaps a well-tailored woven or easy to care for, wrinkle-free shirt paired with your favorite clean-cut denim, suede lace-ups, and a cardigan or sweater-jacket. For an even more refined touch, consider adding a knit tie. The key is to find subtle ways to elevate your look, and sophistication should always be at the forefront.

Daily Reflections on Business Attire

When considering your next off-site meeting at Evergreen Brick Works, afterwork drinks at The Well, or night out with clients along King West, Gallo advises daily reflection on how your attire projects a balance between career ambition and genuine personality.

“We live in an increasingly competitive world, and any man who is serious about his career and social life should understand how you present and define yourself can significantly impact your success,” says Gallo. “Dressing for success boosts your confidence and ensures you stand out and people take notice in a good way.”

“This doesn’t mean wearing something outlandish to grab attention, it’s about intentionally considering where you’re going, who you’ll be meeting, and how you want to be perceived,” he continues. “Whether dressy or casual, a polished and sophisticated look always leaves the right impression while adding flair to your personal style.”

A Reputation Built on Canadian Style

Harry Rosen has a 70-year reputation for quality, precision, and style that celebrates Canadian heritage and individuality.

“At Harry Rosen, we don’t stand still–we have a deep understanding of the Canadian marketplace, and more importantly, we know our customers and we stay attuned to their evolving work environments, lifestyles, and needs,” says Gallo.

“As workwear style unfolds and changes, we’ve adapted our non-traditional offerings to keep you ahead of the trends (i.e. an overshirt over a suit jacket) and tailored our approach to nurture our valuable client relationships and better serve our customers.”

With Gallo and Harry Rosen as your style partners, the outfit you wear on any given workday becomes a quarterly narrative of success, taste, and confidence. It’s a sign of a life well dressed.

Harry Rosen is known for style advice and personalized service. Our team of trusted experts is available to support you with any of your workwear or everyday style needs. Connect with one of our Style Advisors and Book a Style Consultation today.