Meet Olivia
I’m Olivia Gillespie, a New York-based men’s personal stylist and the founder of The Look Society, a custom suiting brand built around the belief that getting dressed should be intentional, personal, and effortless.
My background combines fashion, marketing, personal styling, and product development, giving me a perspective that goes beyond simply choosing what looks good. I’m passionate about understanding how clothing fits, how it is made, and most importantly how it makes the person wearing it feel.
I earned my Bachelor’s degree from the Fashion Institute of Technology (FIT), where I developed a strong foundation in fashion, fit, textiles, merchandising, marketing, and consumer behavior. My education gave me the technical and creative foundation to understand both the product itself and the person it is designed for.
Alongside my education, I have experience in personal and celebrity styling, assisting with fittings, sourcing looks, coordinating with designers, and working closely with clients to create polished and intentional wardrobes. These experiences taught me that the smallest details can make a significant difference...from the way a shoulder sits to the length of a sleeve and the way a garment moves on the body.
My work with The Look Society has allowed me to take that experience a step further.
I’ve become directly involved in the process of developing custom suits—from selecting fabrics and details to communicating with manufacturers and understanding the production process behind a finished garment. Working directly with manufacturers has given me insight into what goes on behind the scenes to turn an idea into a finished piece of clothing.
I believe a suit should do more than simply fit your measurements. It should fit your life.
That means considering your profession, lifestyle, personal style, the occasions you dress for, and the impression you want to make. Rather than encouraging clients to fill their closets with countless suits, my approach is centered around helping them invest in well-made, versatile pieces that they will actually want to wear.
At The Look Society, my goal is to make custom suiting feel more personal and approachable while maintaining the attention to detail and craftsmanship that great tailoring demands.
Because you shouldn't have to change yourself to fit your suit. Your suit should be built around you.
The Look Society
Custom suiting, strategically designed around you.
