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Let’s say you had all the time and money in the world to go shopping for clothes. Would you intuitively know how to choose clothing for our new hybrid working world? Or what about tracking down brands with a strong sense of corporate responsibility? What about choosing pieces from designers who are based in Canada? Or where to find vintage items that would integrate well into your mostly non-vintage wardrobe?

If you found at least one of these consumption conundrums relatable, you can see why personal stylists are experiencing an influx of clientele. While the needs of their consumers change from day to day, the core functions of the role – saving someone time and money, helping people out of a style rut or cultivating the courage to pursue a new look – remain steadfast.

“A big thing is efficiency, and I think people are seeking that in different ways,” says Toronto-based stylist Chanda Chilanga, who started the styling agency Dapper Style Mint (DSM) almost a decade ago. While television and film wardrobe jobs fill up a portion of Chilanga’s calendar, she finds working with private clients just as exciting.

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Toronto-based stylist Chanda Chilanga.Handout

What started as a “side hustle” evolved into something she wanted to do full time. “It’s a reflection of my personality and a lot of the values of the business reflect what I care about which is, at the core, human connection.”

Today, DSM offers services ranging from closet organizing and special event styling to full wardrobe makeovers. The Wardrobe Refresh package starts at $495 and includes a seasonal overview of the client’s closet, styling and shopping sessions and on-the-spot advice over the phone. Clothing budgets are separate from styling services, which Chilanga says enables her team to provide sartorial strategies that suit a client’s financial expectations and schedule.

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“You only have so much time,” Chilanga says. “And you want to spend it doing things that you enjoy. Do you really want to be at a mall for hours?” She points out that, today, it’s not just practical concerns that are propelling personal styling forward. “Now, more than ever, people are paying attention to how they look,” she says. “But what if someone is between sizes or pregnant or they’re changing jobs? And people also want to try new things with their style, yet they might not know where to start. They can engage with someone like me to help them navigate through it.”

Like other personal styling resources, DSM has a clothing donation program. Appointments at Ottawa’s Bayshore Shopping Centre can be reserved in two-hour blocks for $20, and the fee goes toward the local chapter of the clothing-centric employment empowerment organization Dress For Success.

Mary Ciancibello, a wardrobe consultant with a communications background who can be booked through Bayshore’s website, says that the non-profit’s message resonates with her as the daughter of Lebanese immigrants. “We couldn’t afford much, and my mom – one of the strongest women I know – could have really taken advantage of what they do. Its message is about dressing for how you want to feel or the work position you want to get – and that’s exactly my philosophy when it comes to styling.”

Ciancibello recalls her first job in the banking industry in her early 20s, and how her director would send her to get coffee, a task normally relegated to summer students. “I kept saying the summer students were there for that, and she would say, ‘well, stop dressing like a summer student and I’ll stop treating you like one,’ ” she says. “A light bulb went off in my head, and clothing became a communication tool for me.”

She began to build up a clientele of personal styling clients in the corporate world as well as political candidates on the campaign trail. Her roster has grown to include transgender individuals adapting their closets, people who went through a pandemic breakup and “want to reinvent themselves a bit,” postpartum mothers and bullied teens brought in by desperate parents who want to help them build back their self-esteem.

“I talk to them about being their own person,” she says of this impressionable demographic. “That’s really hard to do at their age but coming from mom and dad it’s one thing. Coming from someone who works in fashion, it can be another. After two hours, they’re smiling.”

One common denominator among successful personal stylists is that they know how to build trust with their clients and when to push them outside their comfort zone (and when to hold back). Farhad Younus, who works at Holt Renfrew’s Pacific Centre location in Vancouver, emphasizes that when the person he’s dressing looks good, he looks good.

“Fashion moves really fast,” he says, explaining that he works on a 100-per-cent commission-based scheme. A personal stylist “has to be ready at all times to suggest new pieces.” He adds that as celebrities have become ever more visible through social media, managing expectations is also crucial. Being able to direct customers toward labels that have better-suited fits and fabrications leads to fulfilling relationships. “My clients range from 20-years-old to in their 70s,” he says. “And I have clients who have shopped with me for years, and now their kids come to me.”

Canadian celebrity stylist Karla Welch is also addressing the diversity of consumers with Wishi, an app she co-founded that allows users to virtually interact with stylists from around the world.

Welch – whose client roster is a veritable who’s who of dynamic red-carpet dressers including actors Tracee Ellis Ross, Sarah Paulson, Amy Poehler and Olivia Wilde – says that Wishi’s “fashion-forward but time-poor” users rely on the savvy of the platform’s stylists to keep them ahead of the sartorial curve.

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Stylist Karla Welch’s men’s capsule collection for Wishi.Handout

“Wishi stylists can curate from anywhere,” she says about the benefits of its digital approach, which allows stylists to purchase items from websites around the world rather than just physical stores. The Wishi process starts with a quiz that helps direct a client toward the stylist that best suits their needs and aesthetic ambitions. Services range in price from US$40 for “mini” closet enhancements to US$500-plus overhauls. “Capsules are a Wishi specialty since clients like to mix-and-match items, invest in fewer, good quality pieces and wear them long term,” Welch adds.

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Channelling a scene out of Clueless, DSM’s virtual closet platform records a client’s wardrobe inventory and illustrates how pieces can be worn together, acting as a guide for future dressing. And if shopping local is important to you, Chilanga says that her company strives to put money back into Canadian labels as much as possible. “We work really hard to ensure that our clients are introduced to new designers, and that’s how we support the fashion ecosystem in Canada,” she says.

DSM also addresses another big challenge: greening your closet. “Sustainability is daunting for a lot of people,” Chilanga says. “But it’s just about thinking in terms of how your actions connect with the world. Do you really need the same item in five colours? How are those garments made? How long will they last? I always say we can’t walk around naked, so we can never be 100 per cent sustainable. Fashion is wasteful, and so are other industries – but how can we make good decisions within that?”

This points to another place where a personal stylist can be especially helpful: enabling clients to enjoy the clothes they own for years to come. Ciancibello has a “Rolodex of seamstresses” on-hand to address alteration needs, and Chilanga notes that buying for the long term is essential.

“In Canada, it’s not realistic for us to buy a cheap winter coat year after year,” she. “We want to put a budget toward a really well-made one. This is about understanding how to spend your money, because I’m not under the impression that you’re going to go shopping with me every time. I want to equip you so that you can do it on your own, effectively.”

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