Stylist Jobs in Mississauga, Ontario, Canada
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Stylist - Made-to-Measure
Top Benefits
About the role
Surmesur · Mississauga · Tue to Sat · Base + uncapped commission · $55 to 70K at target · Top stylists earn $100K+
The short version
This is a sales job. A real one, with targets, commission, and accountability. It's also the kind of job where your income goes up every time you genuinely help someone. Not despite that. Because of that.
If you've always felt like those two things should go together, you're right. And this is the role that proves it.
What you'll actually do
You'll guide clients through the full made-to-measure experience: fabric, design, measurements, fit. Every appointment is a consultation, not a transaction. You're here to understand what someone needs, advise them honestly, and build something they'll wear to the moments that matter: a wedding, a promotion, a first suit, a wardrobe that fits who they're becoming.
You'll build a personal book of business. Clients come back. That book grows. After two years in this role, a good stylist has regulars, people who call them, not the store. Day-to-day: client consultations, follow-ups, fittings, CRM entry, boutique upkeep. You own your results.
The money
$55 to 70K in your first full year at target (base + commission) Top stylists earn $100K+. That's real, not aspirational. $550 clothing allowance every six months. You wear what you sell. On us. 60% employee discount. 3 weeks vacation. Group insurance. Group savings program.
No ceiling. Your book compounds. So does your income.
The craft
Made-to-measure is a skill most people never learn. The longer you do it, the more valuable you become, to clients, and as a professional.
You'll learn fabrics, construction, fit theory, body types, and how to read a client's lifestyle and taste from a 15-minute conversation. We train you on all of it. Surmesur has been doing this since 2010 across 10 boutiques in Canada and the US, and we earned our B Corp certification in 2025, which means we take both performance and values seriously.
What we can't teach: the way you treat people. That one's on you.
The path
This role has a real trajectory. Several people currently in management or at our head office started as Stylists. We have 10 showrooms now, with an 11th opening in 2026. The network grows. So do the opportunities for people who perform.
If you want to stay a great Stylist for years, that's valued too. The client book you build is yours to grow.
Who this is for
You've worked in sales, hospitality, premium retail, or any role where performance and relationships both matter—two to three years of that. You know how to read a room, handle objections without being pushy, and follow through without being reminded. You care about style, not obsessively, but genuinely. You notice how clothes fit. You have opinions.
You're competitive. Targets energize you. Commission motivates you. And you're also someone who actually listens, because you understand that the best sale is the one the client is still grateful for six months later.
You follow through. Clients don't get forgotten. Details don't slip.
Who this is not for
If you want a stable hourly job with no performance pressure, this isn't it. If you see commission as a ceiling rather than an engine, this isn't it. If the idea of building a client book over years sounds exhausting rather than exciting. Wrong role.
Schedule
Tuesday to Friday: 11 am to 7 pm · Saturday: 10 am to 5 pm · Closed Sunday and Monday.
Equity, diversity, and inclusion
Surmesur is committed to employment equity. We encourage all qualified candidates to apply, including women, visible minorities, Indigenous people, people with disabilities, and anyone from a marginalized group.
How to apply
Send us your CV and two or three sentences: not about your experience, but about why this role specifically. We read every application and respond within 5 business days.
One more thing: In your note, use the phrase "client for life." It tells us you read this far and you understand what we're actually building.
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About SURMESUR
Established in 2010, Surmesur is a brand with purpose that thrives on human experience, sartorial love and personal development. We aim to be the brand that elevates people to be their best selves every day while making the customer experience the center of our company's success.
Our team is comprised of expert stylists that thrive on creating custom garments based on our client's unique tastes, preferences and needs and designed to truly reflect their aspirations. With a catalogue of thousands of fabrics and additional customizable options, the possibilities of what you can create are almost limitless. You can create suits, shirts, blazers, trousers and other garments, customized from the cut to the finishing, as well as any small detail desired.
Fondé en 2010, Surmesur est une marque inspirante propulsée par l’expérience humaine, l’amour du vêtement et le développement personnel. Nous voulons être la marque qui permet aux gens de donner le meilleur d'eux-mêmes chaque jour, tout en plaçant l'expérience client au centre du succès de notre enterprise.
Notre équipe est composée de stylistes experts qui s'efforcent de créer des vêtements personnalisés en fonction des goûts, des préférences et des besoins uniques de nos clients et conçus pour refléter véritablement leurs aspirations. Avec un catalogue de milliers de tissus de grande qualité et nos multiples options de personnalisation, les possibilités de création sont infinies chez Surmesur. Les chemises, complets, manteaux et autres habits pour hommes sont personnalisés de la coupe à la finition, et ce jusqu’au plus petit détail de style souhaité. Chaque jour, nos conseillers se font un plaisir de vous guider à travers les nombreux choix proposés et vous partagent leur passion pour la mode masculine.