Mr John Legend demonstrates the finer points of wearing black tie .

As a musician, red-carpet regular and serial award winner (one Oscar, one Golden Globe, 10 Grammies and counting), Mr John Legend has worn more than his fair share of evening wear. “I own more tuxedos than one should own,” he says. “I’m guessing around 20. There’s black, midnight blue, brown, velvet, shawl collar, peak lapel…”

And then there are the countless others he’s worn on stage or to events that have been one-offs. “The fact that I’m a performer gives me licence to wear some outlandish things,” he says. “But the ones that I can keep going back to are cool because they fit me just right, they look really good, and they don’t stand out too much to [the point] where people will notice that I’ve worn them a few times.”

Mr Legend, 37, has a lifelong appreciation of good tailoring thanks to his parents. “I grew up in a family with two tailors,” he explains. “My dad was a full-time factory worker, but he was a tailor part-time, and made extra money that way. My mother did, too. They were making clothes all the time, and repairing clothes, doing alterations for our neighbours and friends.”

For Mr Legend, the number-one priority when choosing a tuxedo isn’t the designer, or the style – it’s the fit. “Tailoring is everything, as far as I’m concerned,” he says. “If the suit doesn’t sit right and fit your body perfectly and make you feel confident, then there’s no point. I don’t care who made it, I don’t care what brand it is, it’s got to fit you right.”

Some celebrities have fashion foisted upon them. They become famous and all of a sudden they have a stylist telling them what to wear and dressing them for special events. But Mr Legend has always known what suits him. “I grew up around people who loved fashion, and clothing,” he says. “We went to church, so I was in my Sunday best every week. From the very beginning, I knew how to wear a suit, I knew how to tie my tie, I knew how to iron my clothes.”

How would he describe his signature look now? “I think my style is similar to my music in that I have a lot of respect for classics, and things that are just well made and well executed, with subtle twists,” he says.

To make this film on how to look your best in a tuxedo, we took Mr Legend back to a New York nightspot – one that he and his model wife, Ms Chrissy Teigen, have a special connection to. “It was good to be back at The Box,” he says. “We’ve actually had quite a few fun nights there over the years, particularly when we first started dating, so I had some good memories with Chrissy there. It was cool doing the shoot at that spot, in that neighbourhood, which is where I lived for 15 years.”

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