Expand your career in Luxury

Personal Styling

Watson Style Group is a premier, female-founded personal styling firm serving clients across the country. With headquarters in New York City, Chicago, and San Francisco—and a flagship studio in Chicago—we specialize in delivering highly personalized, wardrobe-transforming experiences for discerning individuals who expect nothing less than excellence.

Our team of expert stylists blends a refined knowledge of designer brands, garment construction, and lifestyle needs with an intuitive, client-centered approach. Powered by our proprietary styling methodology and cutting-edge virtual tools—including digital closets, interactive lookbooks, and curated packing—we deliver an unmatched styling experience rooted in trust, taste, and transformation.

We are currently seeking full-time Assistant Personal Stylists who are passionate about fashion at the highest level—and ready to contribute meaningfully to a firm that is setting the standard in luxury personal styling.

This Role Is Not for Everyone—And That’s the Point

This is a high-performance role in a fast-paced, high-touch environment. We are looking for professionals who are not only obsessed with fashion, but who are detail-oriented, emotionally intelligent, and relentlessly driven to deliver results.

As an Assistant Personal Stylist, your days will be filled with both creative and operational responsibility:

Support Lead Stylists in private client sessions by taking precise notes, managing invoicing, and contributing thoughtful insights as needed.

  • Design polished, editorial-quality shopping boards that elevate and integrate seamlessly into clients’ existing wardrobes.

  • Interpret clients’ lifestyles, locations, and climates with care and sophistication to provide solutions that are both stylish and practical.

Bring extensive knowledge of brands, fit, and fabrication to complete closet edits and support full wardrobe overhauls across body types and life stages.

Why Watson Style Group

This is not a stepping stone. This is a launchpad into a career in luxury fashion styling.

  • Serious growth for serious talent: You’ll be immersed in real client work from day one, surrounded by leaders who expect excellence and are committed to your development.

  • Collaborative, high-achieving culture: We move fast, we hold a high bar, and we celebrate people who show up fully and raise the standard.

  • Luxury with purpose: Our work changes lives. We help clients feel seen, powerful, and aligned from the inside out—starting with their wardrobe.

A front-row seat to personal styling at the highest level: From couture to contemporary, you'll learn the nuanced language of true luxury and build the instincts to match.

We’re Looking for the Best

You’ll thrive in this role if you are:

  • Deeply passionate about fashion and fluent in the language of style

  • Adept in brand knowledge, styling theory, and wardrobe curation

  • A clear, proactive communicator with strong interpersonal instincts

  • Confident describing textiles, silhouettes, and garment construction

  • Highly organized, with elite time management and execution skills

Hungry to grow fast, learn constantly, and deliver excellence daily

If you’re ready to do the best work of your career—at a company that expects your best and supports you in becoming even better—we want to meet you.

THIS IS A FULL-TIME POSITION IN NEW YORK, NEW YORK