Lead with Style. Grow with Purpose.

Watson Style Group is a premier, female-founded personal styling firm redefining luxury wardrobe transformation across the country. With headquarters in New York City, Chicago, and San Francisco—and our flagship studio in Chicago—we offer world-class, client-centered styling experiences that empower individuals to show up as the most confident version of themselves.

We are seeking an exceptional Lead Personal Stylist to join our leadership team. This is a full-time, senior-level role for a stylist with at least 5 years of high-level personal styling experience, a proven track record in sales and client management, and the business acumen to oversee a growing book of business within a service-driven organization.

This Role is for a Stylist with Vision—and Velocity

As a Lead Personal Stylist, you are both the face of the client experience and a strategic driver of the business. You are responsible for nurturing long-term client relationships, curating transformative wardrobe solutions, and growing your portfolio with intention and ambition.

You are just as comfortable selecting couture as you are managing margin. You bring taste, trust, and tenacity—and you deliver results.

In this role, you will:

  • Deliver exceptional personal styling experiences with deep fluency in luxury fashion, fit, fabrication, and lifestyle-specific solutions.

  • Manage a substantial book of business, overseeing multiple client relationships with precision, warmth, and discretion.

  • Drive sales through personalized recommendations, re-engagement strategies, and a refined understanding of each client’s evolving wardrobe needs.

  • Lead and delegate effectively, partnering with Assistant Stylists and team members to ensure every deliverable is executed with excellence.

  • Cultivate and manage luxury vendor relationships, securing exclusive access and negotiating with confidence and professionalism.

  • Develop business growth strategies, identifying opportunities to expand client accounts, improve service offerings, and optimize performance.

  • Work within and manage budgets, ensuring profitability while maintaining a luxury standard.

  • Solve complex client and business challenges with creativity, grace, and a proactive mindset.

What Sets Watson Style Group Apart

You will step into a high-performing, purpose-driven environment with unmatched opportunities to grow and lead.

  • Elevated client experience: Our proprietary methodology, curated digital tools, and client loyalty create a foundation for long-term success.

  • An elite team of collaborators: You'll work alongside talented, ambitious stylists and business leaders who raise the bar every day.

  • An entrepreneurial runway: You will have autonomy, responsibility, and support to grow your portfolio and evolve your practice.

  • Real impact: This work isn’t transactional. Our clients entrust us with some of the most visible and personal aspects of their lives—and we take that responsibility seriously.

The Ideal Candidate

You are more than a stylist. You are a trusted advisor, a business leader, and a confident sales professional. You bring:

  • A minimum of 5 years of personal styling experience, preferably in luxury fashion or high-touch services

  • Proven sales success and the ability to grow and manage a large, loyal client base

  • Experience managing luxury vendor relationships and a network of brand contacts

  • Strong skills in delegation, task management, and team collaboration

  • Comfort operating within budgets and service profitability models

  • A background in professional services or client advisory roles is a plus

  • Exceptional problem-solving abilities, with a high degree of professionalism and poise under pressure

  • A natural ability to connect, communicate, and convert

Ready to style?

If you are a high-performing stylist who’s ready to lead with impact, elevate your career, and shape the future of personal styling—we invite you to apply.

THIS IS A FULL-TIME POSITION IN CHICAGO, ILLINOIS