Assistant Store Manager — ESQ (Bespoke Menswear) — Winnetka, IL

Company: ESQ

Location: Winnetka, IL

Position: Assistant Store Manager

Employment Type: Full-Time

About ESQ

ESQ is Chicago's finest high-end bespoke clothing company dedicated to crafting exceptional, tailored experiences for our discerning clientele. Rooted in quality, elegance, and personalized service, ESQ sets the standard for luxury menswear and women’s tailored fashion in the North Shore. We're seeking an enthusiastic and experienced Assistant Store Manager to help elevate our retail operations and champion our brand values.

Role Overview

As Assistant Store Manager, you’ll be a key leader within the ESQ store. You will support the Store Manager in daily operations, team execution, and customer relationship building, ensuring every guest receives an unparalleled shopping experience. This role is perfect for someone passionate about luxury menswear and delivering exceptional service.

Key Responsibilities

• Support daily store operations and ensure outstanding customer service
• Coach, develop, and mentor sales associates to deliver brand-defining experiences
• Drive sales performance and contribute to achieving store goals
• Manage inventory, merchandising, and visual standards
• Assist with hiring, training, scheduling, and performance evaluations
• Represent ESQ with professionalism and luxury service standards

What We’re Looking For

• Strong attention to detail, communication, and organizational skills
• Passion for menswear, style, and elevated customer experiences
• Ability to work a flexible schedule, including weekends and holidays
• A team player who thrives in a high-touch environment

Compensation & Benefits

We’re offering a competitive salary that reflects the prestige of our brand, the cost of living in the North Shore, and market rates for comparable roles in the region.

Salary Range: $50,000 - $60,000

Benefits Include:

• Competitive base salary + performance incentives
• Full health benefits
• Employee discount on bespoke and ready-to-wear merchandise
• Paid time off & holiday pay
• Career growth and professional development opportunities

Why ESQ

At ESQ, we do more than sell clothes — we craft confidence and individuality. You’ll be part of a team that values creativity, collaboration, and excellence. If you’re a polished communicator with a passion for luxury retail and team leadership, this is the perfect next step in your career.

How to Apply:

Send your resume and a brief cover letter to gewang@esqclothing.com with the subject line Assistant Store Manager — ESQ