On an uncharacteristically warm fall evening, I’m late. Practically running through midtown Manhattan, I’m regretting the cashmere sweater I threw on that morning when the temperature barely surfaced the 50s. A change of clothes would have solved my fall dressing problem, I but as I walk into the showroom of Neapolitan menswear brand Isaia, I realize that I’ve gotten it all wrong. Outfitted perfectly for the weather in a blue and white seersucker suit, crisp white shirt, purple tie and—making the most of every last minute with open-toe shoes—custom white leather thong sandals, Gianluca Isaia has it all right.

Since the 1950s, Isaia’s impeccable fabrics, never-met-a-bold-pattern-I didn’t-love aesthetic and unparalleled knowledge of cut and fit has made the family business a leading force in the menswear market. And if the past few seasons’ expanding sportswear and accessory lines are any indication, Isaia has no plans to rest on its (trademark) coral.

In New York for less than 12 hours, Mr. Isaia, the man behind the brand, graciously sat down to chat about Greek mythology, what he sees for the future of menswear and why men shouldn’t rely on others for style advice.

How did you get started in the family business?

I breathed this business since I was a child and I started following my father [on his travels]. My father pushed me to learn English, and when I was 15 or 16, I started working in a shop in London. I was not selling—I was folding the shirts after the sales people were showing [them] to the customers. I started to get a passion for this work, and so that’s why I decided [to move into it], just after I graduated in April 1989.

Where did the coral branch logo come from?

It started in 2005, so quite recently. We were thinking of changing the label to something Neapolitan. By chance a friend of mine gave to me this piece of coral, and so I said let’s try this coral because there is a lot of connection between coral and Naples. First of all, the [red] color is good luck in Naples; we are a little bit superstitious. Secondly, the very first red coral was found in the gulf of Naples. Third, there is a small town very close to Naples where there is a very long tradition [of making] jewelry using coral. Fourth reason comes from mythology when Perseus cut the head of Medusa. The blood that fell into the sea instantly became red coral.

How do you describe the brand’s personality?

The personality of the brand is a mix of two words: contemporary tradition. That means that we mix together the old tradition of Neapolitan tailoring together with contemporary touch in fabrics—in the cut of the jacket. [We’re] always trying to be different, ironic and fun.

In your world travels, have you noticed any differences in your customers’ style?

I don’t think there’s a difference by nationality; I think there is a difference by age. But when I say age, I don’t mean the natural age—I mean the mind age. So you can have a 35-year-old guy buying same thing a 60-year-old so guy buys.

The key, I think, to be elegant: you have to find your own style. Sometimes they ask me how should I [wear a] shirt, how long [the pants should be]. They are looking for rules, and I don’t think there are rules anymore in the clothing business. I always say I have my rules, but don’t follow my rules—look for your rules. That’s what can make you comfortable when you dress.

Where do you see the future of men’s fashion moving?

I don’t think there are seasons anymore. The people that buy luxury [do not] live in one place every year. They travel a lot; they have the possibility to move around the world. Maybe in August, they are in the mountains so they need cashmere or flannel. Maybe there will be six seasons in the future?

What is one thing that men should remember as they’re getting dressed in the morning?

I think they should choose those things in which they feel most comfortable. If you ask me “Would you go on a stage with the sandals, dressed like that?” I say yes! I feel very comfortable, but maybe you won’t feel comfortable with sandals and a suit. Maybe you would be comfortable with sneakers and suit, so just dress the way you feel most comfortable.

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