How can I make my old black dress feel new for New Year’s? Ask The Kit

“I’m very excited about going to a New Year’s Eve party this year. I know people will be dressing up. I made a vow to rewear my fancy clothes, for both environmental and financial reasons, but my go-to long-sleeve black dress is crying out for some dressing up. What will make my old dress look modern and fresh?”

Rhiannon, Toronto

I think this is my favourite question of the year. Your idea appeals to me so much, Rhiannon (also, excellent name). Real people rewear their best pieces all the time, and I’m so glad celebrities and royals do as well these days.

A black dress is “a brilliant blank canvas,” says Nicholas Mellamphy, Toronto’s king of dress-up. The founder of private shopping haven Cabine in Yorkville, Mellamphy has dressed la crème of Toronto (and N.Y.C., L.A. and Paris) society and celebrity. This fall, he worked with Kate Beckinsale on her fabulous accessories for TIFF.

Mellamphy believes in suffering for fashion. “If you are too comfortable in your New Year’s Eve outfit, start again! That’s my mission statement,” he declares, bemoaning the pandemic era as a “terrible period of comfort dressing!”

Fashion hyperbole aside, he is right. It’s time to deck the halls! “People are wary of investing in a new dress, wondering if they are going to get their money’s worth out of it,” he says. “So I’ve been concentrating on accessories.” He quotes Shirley MacLaine’s “Steel Magnolias” line: “The only thing that separates us from the animals is our ability to accessorize.”

Mellamphy’s first transformative idea is the pin. Yes, pin, not brooch, because both men and women wear pins and “brooch sounds outdated. I wore a pin on my tuxedo lapel to the CAFA awards. It just needed something.” Pins can be found at all price points and are terrific vintage finds — Mellamphy thinks their comeback is due in part to young thrift shoppers unearthing treasures. But his top pin designer pick is Canadian Alan Anderson, who made a large dragonfly pin that Mellamphy sold to “Real Housewives of Beverly Hills’” Sutton Stracke. “That is a statement on the shoulder of a black dress.”

Jewelry works, too: Mellamphy prefers a classic stud earring. For necklaces, he says, “I like things that are a bit tighter to the neck.” He points to a fantasy necklace from Tiffany’s HardWear collection, made of heavy chain links. “That’s my inspiration right now. It’s extravagant but almost casual.” You could easily replicate that chunky chain look with a costume jewelry piece.

Where Mellamphy suggests going all out is on the shoes. “Your shoes should be the whole New Year’s Eve party!” He sends me a flurry of links to dream shoes in soaring colours as we are talking, and I whip through the feathery and velvet confections — a killer retro silver pair from Aquazzura looks like golden age star Carole Lombard might leap out of my phone in them. “You are stepping into a new year, step up your shoe game!” Mellamphy cries.

Next, I chat with Toronto stylist Rita Liefhebber. As senior style director for Jenny Bird, she spends a great deal of time thinking about how jewelry can elevate our looks. Her top advice: “I love pairing a bold earring with a bold bracelet and no necklace; it’s balanced,” she says. Specifically, “a chunky hoop or drop earring, but not too long. Something like the Tome hoops or Nouveau Puff earrings from Jenny Bird.” She is a big fan of a chunky cuff and often wears two at a time for maximum impact.

Continuing on our shoe journey, Liefhebber suggests another footwear path, slightly more forgiving than Mellamphy’s: the low-heel, pointed-tow slingback or mule. (I should note here that Mellamphy called me a quitter because I no longer wear the stilettos I used to.) “The pointed toe along with a sheer black nylon gives the illusion of a longer leg and feels more elegant,” says Liefhebber. She points me to some sculptural Amina Muaddi slingbacks from Ssense, and to a flotilla of more cost-conscious options at Browns and Aldo. She calls out the Browns Couture Nora style, the SJP Paley and the Stuart Weitzman X-Crystal for embellished black evening shoes with very walkable low heels.

Hair accessories are big news this festive season and Liefhebber suggested a lovely black satin hair bow from Sophie Buhai. As for bags, she suggests a terrific slouchy clutch from Aldo called the Specchio, for $80, or a pull-through clutch that sits beautifully on the wrist for a nice hit of newness.

After that, elegant beauty choices can help take your look over the top (in the best way). Liefhebber loves a red lip with gravitas, while Mellamphy says you can’t go wrong with an updo. “I like a tight bun, low on the nape of the neck.”

With that, I’ll wish a happy — and stylish — New Year to all, and home safe.

Shop the advice: Killer accessories to make any old dress feel party-ready

Jenny Bird earrings, $150, jenny-bird.ca SHOP NOW

Stylist Rita Liefhebber suggests accessorizing with bold, but not too long earrings, like this sculptural, curved drop pair.

Browns Couture shoes, $398, brownsshoes.com SHOP NOW

Pointed toe, a low heel, a slingback and a touch of bling: party perfection.

Tiffany necklace, $3,400, tiffany.ca SHOP NOW

A chunky chain-link necklace like the ones in Tiffany’s Hardwear collection add a hit of spectacular style with a little edge.

Naghedi bag, $285, naghedinyc.com SHOP NOW

A pull-through clutch adds visual interest while holding all your night-out essentials.

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