I personally have a fantasy that I will find and buy five miraculous, perfect, flattering outfits that I will then rotate for the rest of my life. I’ve known glamorous women in their 50s onward who have done that, magically switching things up with great jewelry and ingrained confidence. Try dramatic loops of pearls (real or faux, or a mix is even better) for an instant formal look, or big statement pieces of beads or found charms for a more casual styling of the same dress. Et voila! All closet problems: solved.

I continue to cling to my ideal. Dear reader: No one is keeping a PowerPoint record of your outfits. We are all way, way too self-absorbed. We can get the idea in our heads that people snap their fingers and change their clothes, from looking at too much Instagram. Before there was fast fashion, with its great howling maw encouraging us to buy evermore new and newest fashions, people used to have a good suit, a good dress and a couple of pairs of pants/skirts and tops. I love old movies, or movies set in the 1950s and earlier, which prove this. People’s whole closet could fit in a single suitcase! My favourite recent take is the Netflix film about a cleaning lady who splurges on a Dior gown, Mrs. Harris Goes to Paris, where Mrs. Harris, played by Lesley Manville, has about two outfits and one pair of shoes.

The Royal Family might be the best case study for the re-wear. Ever aware of optics around their incomes, they are naturally spendthrift. Queen Elizabeth II was a steadfast re-wearer, sending fashion scribes scrambling to the archives to figure out exactly where we had seen her matching ensemble previously. The apple fell close to the tree, as both King Charles and Princess Anne are notorious re-wearers. Charles, known for his love of good Savile Row tailoring, makes his double-breasted suiting last for decades, damn the current fashions. Sometimes royal things are so old they are new again: Anne’s longtime Longchamp bag recently made headlines for influencing a new generation of quiet luxury fans.

Princess Catherine has worn the same pair of Penelope Chilvers Longtassle riding boots since she was a university graduate. Even Sophie, Duchess of Edinburgh – whose sartorial game has notably stepped up in this time when she and Edward have been thrust into front-row service – was lauded for re-wearing a head-turning purple Prada coat dress at the thin-on-the-ground royal Easter services this year. 

As for Hollywood, look no further than the iconic Jane Fonda as a champion of the re-wear. She swore that the red coat she bought for her Fire Drill Fridays climate activism marches would be the last article of clothing she would ever purchase. She has shopped her closet for all her appearances since the pandemic.

I reached out to two very different but equally stylish experts to flesh out the answer. Nicholas Mellamphy is the new creative director at the designer stronghold The Room at Hudson’s Bay (a return to a position he held previously, bringing his years of experience at his bespoke personal shopping boutique, Cabine, in Yorkville). 

Kealan Sullivan champions individuality (and sustainability) as the Queen of Toronto’s vintage scene. She has been known by the handle “69Vintage” for 25 years, since the days of her Queen Street West storefront of the same name (which morphed into other vintage boutiques, then to markets such as “Hippie Market” and “Sundays at St. Lawrence Market”). She recently changed her business name to “Main Character Energy.” This is germane to the subject of re-wearing, because it points to how we should consider dressing, as the main character of our own stories. 

So we have high-end designer wear and curated vintage treasures: two of the best examples of one-of-a-kind shopping. Sullivan says, simply: “Don’t buy anything you wouldn’t want to re-wear.” Even, she says, if it’s a white T-shirt. “When people buy clothes, they should look at it as the same as decorating their home. Does this piece spark joy? If it doesn’t, why are you buying it?” Sullivan has admittedly remarkable taste, and still wears (and fits into!) things at age 49 that she bought when she was 18. This goes to knowing yourself. As a fashion friend once told me, there are three questions to ask when you buy something: Who are you? What do you do? and Where are you going in that?

Mellamphy says that the rules for Where are you going in that? have changed. “I hear all the time from customers, ‘I have nowhere to go,’” he says. “My answer is: If you like the dress, just wear it. We are way too conscious about how we present ourselves.” Parameters, he says, have changed. “Take a chiffon dress: You can do it up fancy, with high heels and important jewelry. Or you can wear it with a little slide and a raffia bag, like you are in the south of France.”

Stop limiting yourself, he admonishes. “Women have been told for too long, and told themselves for too long, what is wrong with them. Oh, I’m too long-waisted, or my boobs are too big. Just stop. A good seamstress can adjust anything to fit you.”

The rules are all off, Mellamphy adds. “Look at what we learned from Sex and the City: prom dresses for cocktails!” He also cites his work with Suits costume designer Jolie Andreatta throughout the TV show’s original run as a fresh inspiration for him as a retailer. “Clothes can have a new life,” he says. “She taught me that clothes get manipulated to fit the character, not the other way around. A ballgown can become a skirt. A jacket can become a bolero.” Fashion, he says, can be re-interpreted.

Styling, as always, is the key here. “A good dress is a good dress. If it was good 10 years ago, or five years ago, it is good now. If you are building a wardrobe, that is what you are doing. That is not the same thing as having clothes you don’t wear in your closet.”

A story Mellamphy often tells his clients is from the late NYC socialite Nan Kempner. “She said, ‘I always wear something at least three times, so people know I bought it.” 

Sullivan takes this axiom further. “Cost per wear isn’t the biggest concern,” she says. “Buy strong and ask yourself: Does this clothing have balls?” – by which she means, be the main character in your own life. “Nan Kempner would most definitely agree. Good clothing deserves to stay in regular rotation.

Always asking questions,

—Leanne Delap