THE LOOK STRATEGy
ABOUT OLIVIA
I’m Olivia Gillespie, a New York–based men’s personal stylist with a background in fashion, marketing, and client-focused styling. I specialize in helping men look polished, confident, and put together in a way that feels effortless and true to their lifestyle.
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I earned my Bachelor’s degree in Advertising, Marketing, and Communications and my Associate’s degree in Fashion Business Management from the Fashion Institute of Technology, where I developed a strong foundation in fashion, fit, and consumer behavior. Alongside my education, I have experience in both personal and celebrity styling, assisting on fittings, sourcing looks, and working closely with designers to ensure every detail is considered. These experiences sharpened my eye for fit, presentation, and the importance of precision.
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Originally from Cleveland, Ohio, I bring a grounded, approachable perspective to my work and believe that great style should feel wearable, comfortable, and authentic. My Midwest roots influence my styling philosophy: clothing should enhance confidence without feeling forced or overdone.
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Before focusing fully on styling, I worked in marketing and public relations, which gave me a strong understanding of branding, communication, and presentation. This background allows me to approach styling strategically, considering not only how clothing looks, but how it communicates in professional and social settings.
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My work with clients is highly personalized. I take the time to understand how you live, work, and want to show up, then translate that into clothing that supports your goals. Whether building a wardrobe from the ground up, refining an existing closet, or guiding clients through custom suiting, my focus is always on fit, function, and long-term wearability.
Based in New York City, I work with clients locally and virtually, offering a tailored styling experience built on trust, ease, and lasting results.