6 Gorgeously Tailored Pieces And The Stories Behind Them

We’re buying more clothes—and wearing them for less time—than ever before. One way to make the most of what you already have? Working with a tailor to alter and update a beloved piece or a vintage find that needs some TLC. For inspiration, here are six gorgeously refreshed pieces, and the stories behind them.

Dr. Liza Egbogah

“I like to wear bright, vibrant outfits, especially at the clinic where I work as a manual osteopath, because it puts people in a good mood. A few years ago, I went on a trip to Dubai with my mom. Whenever I travel, I like to treat myself to an item of clothing or an accessory. Those are the only kind of souvenirs I collect—it’s like wearable art.

While visiting the city’s famous souks, I found myself gravitating towards clothing stalls filled with beautiful bejewelled pieces in vibrant colours. The owner of one of the stalls served us black tea with sugar as he showed us a selection of gorgeous caftans. Two really stood out to me: a cobalt blue and a fuchsia, both made from a beautiful sheer silk chiffon. I immediately thought “I need to have that.” The only problem was that they were floor-length. I’m all limbs, so short dresses that highlight my legs tend to look better on me. I knew that if I had them shortened above the knee, they would be more flattering on my figure and I would be able to wear them to cocktail-attire events.

I had the caftans tailored at the stall I bought them from, and it added a youthful vibrance to both. In the past decade, I’ve gotten a lot of wear out of them, either with a matching slip dress to a friend’s wedding or over a sports bra and bike shorts on nights out. I love the details on the neckline because they add a bit of sparkle to any outfit without being over the top. Every time I wear the caftans, I feel amazing and I’m reminded of a great trip with my mom.”

Judith Kennedy

“My husband took many trips up to Northern Ontario in the late ’60s. In 1969, he travelled to Moosonee, a town just south of James Bay on the banks of the Moose River. There, he met a Cree woman who did traditional beadwork, and he had a pair of deer-hide and fox-fur-trim moccasins custom-made for me. After that, I never owned another pair of slippers. I wore them every day, and as the deer hide got thinner and thinner, I patched them up with epoxy glue and duct tape. I would lovingly caress them, saying, “Don’t go!” But even though I had worn holes in the leather, the floral beadwork looked as good as the first day I got them. My granddaughter introduced me to her friend Olivya Leblanc, a Toronto-based Wendat artist and beadworker with French-Canadian and Slovenian roots who runs a business called Harvest Moon Designs. At the time, she was perfecting how to make moccasins, and I asked her to repair mine.

Olivya replaced the worn leather with sturdy moosehide from an Indigenous-owned company called Tribal Spirit Music in Quebec and got the fox fur from Bill Worb Furs, a furrier in Winnipeg. She even tried to locate the woman who made them. While she couldn’t find her, Olivya did recognize the beading as a classical Cree beadwork pattern. When she returned the repaired moccasins to me, I held them to my chest and started to cry.

My husband passed away five years ago, and these moccasins are so dear to me. They represent 55 years of memories. They’re one of my most treasured possessions.”

Adele Tetangco

“When I was a kid, my parents used to take me on trips to the Philippines, where they’re from, and on our way back to Canada we’d always stop over in Hong Kong. In the markets, they had stalls where you could get clothing tailored on the spot. So I was familiar with that practice from a young age. I’ve always loved fashion—my style is a cross between Dorothy in The Golden Girls and Sigourney Weaver in Ghostbusters II—and when I fall in love with something that doesn’t quite fit, I’ll buy it anyway because I know I can always get it tailored.

My dad retired in 2006 from his job at Fields, a chain of department stores in Western Canada, where he was a buyer for over 20 years. He wore suits to work every day. I particularly remember him wearing an olive-green one that was quite big on him—it was the style of suits back in the ’90s. When my mom cleaned out the closet and got rid of all of his old work clothes, I swooped in to rescue a few pairs of business slacks: the olive-green ones from my childhood, as well as basic black trousers.

This was around the time when baggy trousers made a comeback. I brought them to my tailor so she could alter them to fit my five-foot-11 frame. I had her slim down the silhouette, shorten the inseam and take some extra fabric out of the crotch. I sent a picture of myself wearing the pants to my parents, and they thought it was funny. My dad couldn’t believe I was wearing his old pants. It feels nice to wear something that belonged to my dad—it made me feel closer during lockdown last year when I couldn’t see him.”

Karen Cleveland

“Shortly after I married my husband in 2014, my mother-in-law, Sheri, asked me if I would be interested in her mother’s mink coat that had been kept in storage for years. I never had the opportunity to meet Pearl—she passed away before I met my husband—but I always heard stories about what an amazing woman she was. Of course I said yes. I was worried it wouldn’t fit— they were both petite women, barely five feet tall and quite slender, while I’m five foot four and have a more muscular build, but I lucked out because the coat was quite voluminous. The roomy, floor-length style had been very popular in the ’50s, but it felt dated, so I asked Sheri what she thought about updating it to a more modern silhouette. We share the philosophy that there’s no point in owning beautiful things if they’re just going to be collecting dust at the back of your closet, so she agreed.

I took the coat to be altered at Charisma Furs, a furrier in Toronto. To turn it into a contemporary everyday piece, they shortened the sleeves, fitted it through the chest and waist, and took up the hem to hit just above the knees. Then, I had the remaining fur turned into a shawl that I like to wear over a leather jacket.

I’m quite a low-key dresser, but I wear the coat all the time. It’s a statement piece, but it’s also the warmest one I’ve ever owned, and it was customized to my body, so it fits perfectly. Pearl was an amazing woman—she was a fierce advocate for seniors’ rights—and I feel connected to her every time I wear it.”

Janu Yasotharan

“Everything I wore to weddings, family events and church growing up was made with love; in Tamil culture, we hand-make and tailor almost all of our clothes. When my mom left Sri Lanka because of the civil war, all she carried with her was her wedding sari and two others that belonged to her mother. There’s a picture of me on my fourth birthday wearing an outfit made from one of those saris.

Four years ago, I got sick and my weight started fluctuating. I started dressing all in black to hide. As a woman of colour, I’ve been taught to minimize myself, and I realized that was translating into the way I dressed. I stopped buying all black clothing and started looking for vibrant, bright items that I could have tailored to fit my body.

I love thrifting because you can find unique pieces. I got this multicoloured plaid blazer at Value Village for $2.50. It had shoulder pads and a built-in shirt panel, but the pattern reminded me of the ’90s movie Clueless. My tailor shortened the sleeves, updated the silhouette and neckline, removed the shoulder pads and swapped the buttons with vintage brass ones I salvaged from a different thrifted top.

Having something that fits me perfectly is exhilarating. When I put on this jacket, I feel alive. It makes me think, “I am here, I am colourful, I am bold.” I feel a sense of self-confidence that I know radiates outwards. In those moments, I need the world to hold space for me because I’m commanding it.”

Odessa Paloma Parker

“As a teenager, the most exciting thing I could do was trek to downtown Toronto from Scarborough with a group of friends and spend the day wandering along Queen Street, going in and out of all the groovy shops that used to be there. I started buying vintage clothing when I was in high school in the mid-’90s.

My style trademark involves lots of colours and patterns, all mixed together. I was instantly drawn to this dress’ structure, the cute pussy bow at the neckline, and the hectic pattern. I hadn’t seen a colour combination like it before. Even as a vintage aficionado, it really stood out to me. It’s from Leslie Fay, an American department store brand from the ’50s and ’60s, and there’s a label inside that notes that it’s union-made.

The dress fit perfectly everywhere except for the sleeves, which were far too short and made me look like an adult dressed up in kids’ clothing. One thing you learn pretty quickly while vintage shopping is that the clothing proportions were different back then. I had a friend with a sewing machine take the sleeves off for me.

Tailoring gives you the option not only to buy an incredible vintage piece that no one else is going to have, but also to personalize it to your exact measurements. Buying vintage is also a way for me to have the variety I need in my closet while reducing my environmental impact. I know it can be intimidating because you don’t necessarily know where to start or what you’re going to find, but if you let go of your expectations, it can be such a freeing way to shop.”