I think that how you present yourself through your attire can be a key indicator of your personality and character. If you’re dressed well, people are naturally going to respect you more and subsequently listen to what you have to say. I have a lot of fun underscoring my personal values through my fashion choices. Whether it be more literal, such as a phrase or word applied on a shirt, or more informal, like supporting a friend’s brand or wearing a bracelet that holds personal significance, fashion and philanthropy have always been intrinsically linked. As part of a gala I founded and chair for Canada’s TELUS Friendly Future Foundation, I collaborated with the London-based women’s brand ‘Me+Em’ by Clare Hornby and the Toronto-based men’s brand ‘Christopher Bates’ to create T-shirts that embody hope for young people. This initiative was one of the fundraising methods that allowed us to raise $2.5 million for underprivileged youth in Canada and beyond…”
Jay McCauley, Philanthropic Advisor
Jay McCauley is a strategic communications leader and philanthropic advisor providing high-impact support in branding, public relations, political strategy and Gen Z engagement to major corporations and nonprofits. He has held key roles advising two Premiers, a Leader of the Opposition, a Prime Minister and the CEO of one of North America’s largest publicly-traded companies. Jay is the youngest board member in Canadian nonprofit history, and serves on the boards of ComKids, Boost for Kids, The Shoebox Project, TELUS’ Toronto Community Board, and The Duchess of York’s Youth Impact Council. He has helped raise more than $20 million through service on over 20 charity boards and has been named 30 Under 30 by BCBusiness, ‘Under 30’ by Business Elite Magazine and Young Professional of the Year by Notable Life…
C&B: “Jay, congratulations on being named on the CITY & BEACH INTERNATIONAL BEST DRESSED LIST 2025! As we enter a new season of parties, fundraisers, and events, how do you balance professionalism with personal flair in your wardrobe?”
JM: “Thank you! For me, I would always rather be overdressed than underdressed in any circumstance. I believe it’s really important to ‘read the room’ when it comes to a personal, professional, or charitable event. Adhering to any dress code is a sign of respect – for the event, for the organisers, and for myself! While working, and especially while at the office, I always wear a suit…”
C&B: “As a global ambassador, how do you incorporate cultural influences into your fashion choices?”
JM: “Having both lived and worked in multiple cities and having had the great privilege of traveling all over the world, I know that my style has been influenced by the experiences I’ve had and the people I’ve met. The North American, British, and European styles all have different niches and aspects that I can appreciate. North Americans are riskier; for example, you’d see more casual influences in formal dress, whereas the Brits are fairly firm and classic. I’m not a major trend hunter, and I think it’s more important to embrace personal trends versus copying or emulating what someone states is ‘on trend’…”
I’ve always embraced a classic look, and I love matching my shoes, clothes and accessories. Like many, I get inspired by Instagram and have a folder of plenty of ‘looks’ that I then emulate. My Alexander McQueen white sneakers are a major part of my wardrobe. I love Suitsupply for suits; they have such fantastic variety. For casuals, I love James Perse and AllSaints. For basics, I love Mango men’s – their black jeans are still the most comfortable I’ve ever worn! James Dean has always been a historical inspiration for my personal style and vibe. I’m often clothed in darks and whites, rarely embracing colour, but recently I’ve been slightly more adventurous when it comes to adding colour into my wardrobe…”
Jay McCauley, Philanthropic Advisor
C&B: “What are your go-to fashion staples for traveling and attending international events?”
JM: “I’m starting to master the art of packing for international travel, which can be a challenge, especially when I have a number of events lined up over several days! My rule of thumb is to always have two full dark suits, a tuxedo jacket, and two crisp white dress shirts. I can mix and match with that assortment quite easily. I love wearing a double-breasted jacket, so I’ll usually include one of those, and if I end up needing to attend a last-minute black-tie event, I can always find a bow tie or regular tie in my carry-on…”
C&B: “Thinking of this coming Autumn/Fall, have you noticed any emerging trends that you think will dominate men’s fashion in the coming months?”
JM: “I’ve noticed a lot of draping and layering taking place in both casual and formal wear — which I love! I think sometimes men’s classic fashion can seem boring, so adding in a touch of flair via a draped sweater or layered quarter-zip is a great way to switch things up. Something I’ve noticed and embraced in my own fashion is stacking accessories. People are stacking their wrists with all types of accessories, mixing a $1 friendship bracelet with a $75,000 watch. It’s awesome…”
For travel, especially if I’m going on an overnight flight, I like to carry a garment bag with a pair of sweatpants, a comfortable jacket, and some hotel slippers so I can rest and feel super comfortable during the flight. On busy days, I’ll always make a conscious effort to wear something comfortable yet fashionable. Sneakers, black jeans, a black T-shirt, and a jean jacket is usually my go-to ‘on the run’ look. That being said, I co-chaired a Masquerade Ball at Toronto’s Casa Loma, and my co-chairs and I were literally in full workout gear running around the castle getting things set up for hours, up until 30 minutes before the event! Sometimes you just have to go with the flow…”
Jay McCauley, Philanthropic Advisor
C&B: “Talking of accessories, what are the must-have accessories for a serious philanthropist and communicator such as yourself?”
JM: “Personally, I like wearing one of my classic watches, and I receive many compliments about my signet ring with my family’s crest on it. However, for events, galas, and long work days, I’d say the most important accessory for me is a portable charger for my phone!”
C&B: “Finally, as one of the male VIPs on our BEST DRESSED LIST 2025, what specific advice would you give to young professionals looking to develop their own unique style?
JM: “I’d say that your most important client is yourself! A lot of people suggest ‘taking risks,’ which I don’t have an issue with, but I don’t think it’s useful to take risks just for the sake of it. Everyone’s personal style and brand evolve differently, so I’d suggest starting to model fashion choices by observing those you admire or respect. Individual personality develops naturally, and the same goes for fashion; the most important aspect is to feel confident and content within your own skin…”
CONTACT: http://www.jaymccauley.ca
