Two decades ago, one of the most in-demand women in the world was someone with a career many of us didn’t even know existed. That woman was Rachel Zoe, and she was a stylist. Zoe was linked to every cool aughts celebrity, like Mischa Barton and Nicole Richie, and she draped them in decade-defining bohemian-chic looks that many of us tried—and debatably failed—to emulate. A lot has changed since then. Today, celebs aren’t the only ones with access to an expert who can curate their wardrobe or advise them on what to wear to an event. In fact, among certain circles, it now seems that having a personal stylist is almost as important as having a therapist.

Many people are experiencing sartorial confusion thanks to a lifestyle switch prompted by the pandemic, and they’re looking for an expert who can help them build a wardrobe that better matches their new lives. There’s a slew of stylists who fit the bill, and they’re available for one-on-one appointments—both virtual and in person—to help you edit your closet and style everyday looks. They can also take you shopping and select items for a wardrobe overhaul as well as send you a style guide each month highlighting the best pieces to shop. And they offer these services for every budget and need, ranging in price from as low as $50 to well over $1,000.

But here’s the thing: A good stylist won’t just help you feel better in your clothes—they’ll help you feel better in your own skin too. “Ninety percent of my clients are women going through some kind of transition in work or life or who feel that their body has changed,” says Joy Asibey-Gabriel, the Toronto-based founder of personal-styling service Black Lady of Leisure. “It’s my job to not only put them in outfits they look great in but also help them be more confident”—which is, unarguably, the most essential element of dressing well. On your own personal-style journey? Let us help you find your perfect stylist. Here are a few of our favourites in Canada:

IF YOU LOVE BEING THE COOL GIRL: CHARLY GOSS STYLE INC.

 

Charly Goss’ stylists are known and adored for their tough-love approach. “I tell it like it is, so if that’s gonna hurt your feelings, then take a hike,” wrote Goss in one of her first Instagram stories after launching her company in 2021. “But if you’re ready to up your style game and take back the streets, then you’re in the right place.” Goss passed away from cancer in July 2023, but she taught her team to be just as candid as she was about which trends are in and which are out to help clients look and feel decidedly cool.

Most people who reach out to the team are moms who are short on time and looking for help putting outfits together, says lead stylist Amanda Telesca. She and Charly Goss Style Inc.’s other stylists offer wardrobe overhauls that are conducted virtually or in person (primarily in the Greater Toronto Area), and they pre-style outfits and photograph them for clients to make getting dressed quick and easy. The company’s most popular offering is a membership program, the main attraction of which is access to style guides (over a dozen a month) packed with affordable products to shop and tips on how to wear them. (Think a monthly “cool mom” guide with pieces like knit bombers and barrel-legged jeans.) The membership also includes access to a Facebook group where members can have their fashion questions answered by a stylist or fellow member as well as automatic entry into monthly giveaways with seriously covetable items, like a Toteme bag.

CHARLY GOSS STYLE INC. STYLE TIP: Only buy something if you can wear it three ways. This will ensure that you’re purchasing with intention and considering the longevity of each item.

IF YOU WANT TO ELEVATE YOUR PERSONAL BRAND: JULIANNE COSTIGAN

“When you feel incredible in your clothing, the possibilities for your personal and professional success are endless,” says Julianne Costigan, founder of her namesake styling firm. So it’s no surprise that her hero service is an event aimed at helping women look and feel better—at work and beyond. Called Portraits With Impact (PWI), the biannual ticketed Toronto gathering welcomes women to reserve their spot to be styled by Costigan for a photo shoot with a professional photographer and gives them access to an empowering thought leader, such as a LinkedIn consultant or a confidence coach. “When women leave, they feel transformed and changed for the better,” says Costigan. Her team also hosts bespoke PWI events and style master classes throughout the year for corporate clients.

Looking for one-on-one support? Costigan offers private styling sessions. They typically begin with a survey to identify the client’s personal style, and that’s followed by mood-boarding, a closet cleanout and shopping at two or three stores where Costigan or another stylist has pre-selected pieces. Her team also digitizes closets (by uploading pictures of every wardrobe item onto an app) so they can put outfits together virtually for clients at any time and for any occasion. Those looking for a personal stylist without the premium price tag can instead sign up for a paid subscription to Costigan’s monthly digital style guide, which is packed with affordable fashion picks.

JULIANNE COSTIGAN STYLE TIP: If you wouldn’t buy it at full price, don’t buy it on sale. This will help prevent you from having a closet overflowing with pieces you can’t make sense of—and don’t truly love.

IF YOU’RE AFTER TIMELESS STYLE: MABELLE STYLE

Accountants, lawyers, doctors, engineers and other nine-to-five professionals tap Vancouver-based Lindsay Wilkins of Mabelle Style for help creating their work wardrobes—particularly when their bodies have changed and their clothes don’t fit the way they used to. “One thing stylists are good at is knowing how to read people’s shapes and style different ones,” says Wilkins. “The best part of my job is when people tell me they have confidence they’ve never had before.”

Clients seek her out for her classic, minimalist aesthetic and for help building seasonal wardrobes. Wilkins offers virtual consultations where she has clients complete a questionnaire about what they’re looking for and then examines their closet. Next, she provides a shopping list of hand-picked items that’ll help them build a more-well-rounded wardrobe. Her most popular service? In-person shopping sessions. Wilkins pulls pieces at various stores and takes clients to try them on and purchase what they like. She then creates a lookbook full of all the pieces they’ve purchased and already own and styles two weeks’ worth of outfits that’ll help her clients look great while still feeling very much within their comfort zone.

MABELLE STYLE STYLE TIP: Most people wear only 20 percent of their wardrobe—the goal should be 100 percent. Aim to build a wardrobe that you love and that only has pieces you want to wear regularly.

IF YOU WANT TO CHANNEL YOUR DEEPEST SARTORIAL DESIRES: BLACK LADY OF LEISURE:

Joy Asibey-Gabriel, founder of styling company Black Lady of Leisure, sees herself less as a stylist and more as a coach. “I call myself a ‘feminine adornment coach,’” she says. “My approach is about helping women figure out what they want to express through their clothes.” Her average client is in her 40s, works in a creative field or as an entrepreneur and can work with Asibey-Gabriel in two ways: in-person sessions in Toronto for eight to 12 weeks or virtually in a group for eight weeks.

There are three stages in Asibey-Gabriel’s process. First, she uses thoughtful activities like meditation to help clients understand who they are and who they want to be. In the second stage, she analyzes their wardrobe based on their goals and lifestyle and identifies what’s lacking. In the final stage, she edits their pieces and helps them style 14 days’ worth of outfits.

Asibey-Gabriel’s greatest flex is teaching her clients new ways of wearing the clothes they already own. “I get a lot of satisfaction when a woman realizes she has all the treasures in front of her already,” says Asibey-Gabriel. “On one level, it’s a great metaphor for the idea that more often than not, we have everything we need—we are already that which we seek. We might simply need a helping hand to see it.”

BLACK LADY OF LEISURE STYLE TIP: Create a list of fun pieces you own or want—the ones that light you up and suit your personal style. Then commit to playing dress-up with one every week.

IF YOU’RE AFTER A SPECIFIC LOOK: WARDROBE DETECTIVES

Whether it’s a tween wanting a Wednesday Addams-inspired wardrobe, a retiree preparing for his new travel-focused phase of life or a company that wants to help staffers dress for the stampede—all of them look to Calgary-based stylist Gabi Conac for help. She’s the owner of Wardrobe Detectives, and she has a knack for helping people find their unique style—or embrace cowboycore. “As a stylist, you have to know how to create any aesthetic in a beautiful way,” she says, “and help your clients feel like that aesthetic is for them.”

Conac offers wardrobe audits, which can be booked online or, if you’re in the Calgary area, in person. She sifts through a client’s wardrobe, editing it to align with their style goals, while educating them on styles and sizes. Her in-person shopping service puts those lessons into action, helping clients break old habits and embrace new silhouettes. Afterwards, she creates three or four outfits for every new item and takes photos of each to create a lookbook.

But she offers more bespoke services too. Aside from corporate events where she helps companies redefine business casual or instructs employees on how to dress for an event, she specializes in vacation style. Want help packing for a trip to Italy and have The White Lotus’ Tanya as your style inspo? Conac’s on the job—and if necessary, she’ll make sure it all fits in a carry-on too.

WARDROBE DETECTIVES STYLE TIP: When you see an outfit you like on a celebrity or influencer, be inspired by it but don’t recreate the exact same outfit. Stay true to your personal style.

IF YOU’RE LOOKING TO DRESS LIKE YOURSELF BUT BETTER: LA CLOSETTE

 

What might draw you to stylist Irene Kim is her unique personal style (like how she pairs a fringed camel blazer with opaque red tights and a sheer sequined skirt). And one of the reasons you might keep booking sessions with her is for all her handy tips. (That sequined skirt? It is from Prada’s 1999 collection and is a thrift-store find; she had the lining removed for a more modern feel.)

Kim, who’s the co-owner of Toronto-based styling firm La Closette, tends to attract people who range in age from 30 to 65 and are drawn to the way she dresses for everyday life (distinctive and within a fair budget) but struggle with getting dressed themselves. “I encourage my clients to think about what they like and understand what style resonates [with] and feels good to them,” she says.

During in-person and virtual styling sessions, Kim educates clients on which pieces in their closet may not be working for them and how to make their clothes more versatile by wearing them in creative ways. After the closet session, she takes local clients shopping and sends product links to faraway ones to help them lock down what they lack when it comes to building a foundational wardrobe. Whether in the change room or virtually, she has clients show her each new item—even if they think it’s a “no”—so she can show them how they could wear and style it. Want to learn Kim’s styling philosophy for the mere price of a latte? Subscribe to her Substack, In Moda Veritas.

LA CLOSETTE STYLE TIP: To get the most versatility out of your wardrobe, mix dressier pieces with casual ones. This is a good way to vary the formality of an outfit and take it in a fresh stylistic direction.

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