Location: Chicago. In-person at our River North showroom
Compensation: Commission-based, with first-year earnings of $60–70K+, $90K+ in year two and beyond
Benefits: Health, dental, vision, 401(k), paid time off, employee discount
Application requirement: Cover letter is required to be considered

About Custom Suits You
Since 2005, Custom Suits YouTM has specialized in bespoke menswear, attracting clients from around the world who fly to Chicago to be fitted for one-of-a-kind suits and shirts. Every garment is made to the client’s exact specifications — a true luxury experience from first fitting to final delivery.

About the Role – Full-Time Luxury Sales & Styling Job in Chicago

We’re looking for a driven, client-focused Sales & Designer professional to join our team full-time in Chicago at our River North showroom. This is a great opportunity for someone based in Chicago or nearby who’s passionate about luxury fashion and high-end client service. You’ll work directly with clients both in-person and virtually, guiding them through the entire custom clothing process — from fabric selection and fitting to final delivery.

This is a commission-based sales role ideal for someone who thrives in a high-touch, client-driven environment and has a strong appreciation for luxury menswear.

Key Responsibilities
• Build and nurture relationships with upscale clients
• Guide customers through the custom clothing process from consultation to final fitting
• Host in-person and video appointments to recommend fabrics, styles, and fits
• Provide exceptional service and personalized attention to every client
• Maintain detailed knowledge of current menswear trends and product offerings
• Track and meet personal sales goals and client retention metrics
• Manage client communications, orders, and follow-up using CRM systems

Who You Are
• Naturally personable, with strong interpersonal and communication skills
• Confident working with an upscale client base
• Goal-oriented, driven by results, and energized by a commission-based environment
• Highly organized with strong attention to detail (yes, we’re mentioning that twice)
• A quick learner who can multitask in a fast-paced setting
• Familiar with or passionate about luxury fashion and custom suiting
• Previous experience in retail sales or fashion is an asset

Education
• Bachelor’s degree required
• A degree in fashion, marketing, business, or a related field is a plus
• Fashion school or training in menswear/styling is considered an asset

Perks & Culture
• Training provided in custom fitting, styling, and sales
• Collaborative, energetic, and goal-driven team
• Opportunities to grow within a premium menswear brand
• Strong emphasis on innovation, learning, and industry excellence

To Apply
• Please email your cover letter and resume. In your cover letter, feel free to include:
• What “goal-oriented and ambitious” means to you
• What matters most to you in a role

We are hiring locally in Chicago and encourage applications from those who are passionate about luxury retail and client-facing sales.