We asked Larry Rosen—son of Harry and CEO of the sartorial empire that his father built—to tell us where men’s fashion is heading. Here, the 53-year-old sounds off on the importance of eyewear, cufflinks and wearing suits in the summer.

Harry Rosen CEO Larry Rosen (Photo by Jenna Marie Wakani)

A lot of younger guys are adding suits to their wardrobe, even when they’re not required for work. What is your take on the suit’s enduring popularity?
It’s a proven form of making a statement of power and authority, and women will tell you that it makes a man look sexy. I always adhere to the idea that you can never overdress; you can only underdress.

What other rules always stay in fashion?
“God is in the details.” In the morning, I think of every aspect of dressing. You won’t see me in a suit without a nice pocket square, a nice tie, a nice shirt and the right cufflinks. I’m not like Niles from Frasier, but I like to pay attention to everything.

Where do you shop?
I run half-marathons and I get my gear from New Balance at Yonge and St. Clair. Other than that, everything except my glasses is from Harry’s. My eyewear comes from Josephson Opticians (60 Bloor St. W.). They carry Robert Marc frames—very smart and elegant. I have three or four pairs. I change my glasses every year because it’s important to keep updating your look. If you wear the same glasses for 10 years, it says that you’re not really evolving.

Cufflinks were out for a while and now they’re back. What are “the right cufflinks”?
I’ll often wear a pair with a spider, frog or eagle design, and sometimes I’ll wear a frog on one cuff and an eagle on the other. This business used to take itself way too seriously. There were too many rules, like you can only wear cufflinks with a really dressy suit. There’s something so boring about wearing a dark suit, a white shirt and a black tie. Wear an orange tie, wear some cufflinks, have some fun and wear fancy socks. I like paisley socks.

But even the best of us have momentary lapses in our fashion sense.
On my 50th birthday I was given a collage of old photos of myself and I laughed at how big my glasses were in the ’80s. I could have gone swimming in those. I also wore banded collars. But these elements don’t look wrong to me—even the big glasses are charming because they help date the photos and define what was big at that moment.

It’s 30°C outside. How can men look good without breaking out the default shorts and T-shirt combo?
A man will always look great in a tan suit. In this weather, he can wear one with a blue shirt, look like a million bucks and stay as cool as a cucumber, on account of the lightweight material.