A nice dinner date is the classic idea for February 14. And as New York menswear writer and designer Alan Flusser once told me, “If you walk into a restaurant and you’re not known and you want to get a good table, a suit and tie will go much further down that road than any other form of dressing.”

Unfortunately, a decade of casual Fridays has left many men bereft of a suit or the knowledge and confidence to wear one.

Some men say they feel like their dad when they don the two-piece ensemble. Others can’t break their association with, as Metropolitan Museum of Art curator Andrew Bolton put it to me, “workplace sobriety and conformity”.

So how do you fun up the suit and avoid Willy Loman–esque anguish?

On the line from Toronto, Joe Chiaramonte, Tip Top Tailors’ buying-department manager, says you have to start with the cut. “A slimmer, fitted, tailored look is popular these days. And anything in black is the leader.”

As a starting place, Chiaramonte recommends selections from Tip Top’s Bellissimo brand and the mid-market Calvin Klein label for an au courant look.

But not everyone is willing to spend money on a new suit, especially if a conventional one is already languishing in the closet. So why not breathe new life into your neglected three-buttoner?

One of the best ways is to improve your peripherals with a great-looking shirt or a lightweight sweater, which can amp up a suit and later be introduced into your regular clothing rotation.

Melissa Jurcevic definitely likes the idea. (Fiancé: take note.) She’s the co-owner of Hum, a women’s boutique on Main Street that hopes to bring in a men’s line this year. She doesn’t like ties and pocket squares for a Valentine’s date, but ?seeing a man “making an effort ?would be kind of nice”.

During a trip to Holt Renfrew in Pacific Centre, Jurcevic goes for a button-down shirt by Modern Amusement. “I like things simple and muted but with little details you don’t see on everybody else that give your clothes that edge.” In this case, the edge comes from Yankees-like stripes and cloth-covered buttons.

At $140, the shirt costs more than some suits, but Jurcevic points out this is an exercise in tricking out the ordinary. “Plus it goes great with denim.”

Then it’s off to Harry Rosen, also at Pacific Centre, where she spots a Hugo Boss V-neck sweater made of wool, silk, and cashmere that literally makes her gasp. Dotted in a pick-and-pick pattern with teal, camel, and chocolate, the sweater mates perfectly with a no-longer-plain blue suit. “It just switches things up for a nice night out,” says Jurcevic.

That’s all fine and dandy, but some suits are simply out-of-date, with four-button fronts or low-button stances. What to do then?

You find a surgeon, someone bold enough to take your suit apart and put it back together in a modern key. You find a man like Ioan Petrescu. He runs Johnny’s European Tailors (3258 West Broadway) and is an eminently confident man. “If you know how to do it, you can do anything,” he says at his shop.

Adding working buttons on a jacket sleeve?

“No problem.”

Narrowing the shoulders and nipping the waist?

“Yes, yes, shoulders, $45.”

Turning a conservative three-inch lapel into a skinny one? “Three, four hours’ work.”

Petrescu will even move a low notch (where the collar meets the lapel) and alter it so it sits higher, at the current clavicle level—which is the tailoring equivalent of a head transplant. But he can do it.

A less radical, cheaper suggestion is to simply stick with a nice shirt and a one-colour knitted tie, and just change the buttons. That’s right: buttons.

According to Colleen Miller, owner of Button Button in Gastown, “One of the best ways to improve a suit is to upgrade the buttons.”

Replacing plastic with horn or vegetable ivory can subtly turn a plebeian garment into a sensual luxury.

Says Miller: “I recommend vegetable ivory buttons made from the nut of palm trees. They have a nice buff to them, they’re not really matte, and they make the garment. And it feels so nice to touch them.”

And isn’t that what we all want—someone to touch our buttons?