Jonathan O’Toole is a Professional Clothier with Tom James Company, serving clients throughout Lakeland, Polk County, and Central Florida. Based in Polk County, Jonathan works with executives, business owners, attorneys, real estate professionals, and other professionals who value looking their best without spending their time shopping for clothes.
A graduate of the University of Central Florida, Jonathan brings years of experience in relationship building, sales, and client service to his work as a custom clothier. He provides a highly personalized, in-home and in-office clothing experience, helping clients build wardrobes around their profession, lifestyle, personal style, and day-to-day needs.
Jonathan specializes in custom men’s and women’s clothing, including custom suits, sport coats, dress shirts, trousers, casual clothing, and complete professional wardrobes. Through Tom James Company, he brings the custom clothing experience directly to his clients, handling everything from wardrobe planning and fabric selection to measurements, fittings, alterations, and ongoing wardrobe management.
His approach is straightforward and relationship-driven: make getting dressed easier, make sure every piece earns its place in the closet, and provide a level of personal service that extends well beyond the initial order. Whether a client needs a custom suit for an important event, an updated business wardrobe, elevated casual clothing, or simply a better-fitting everyday closet, Jonathan helps create a wardrobe that feels natural to the person wearing it.
Outside of work, Jonathan is an active member of the Lakeland Rotary Club and enjoys being involved in the community he and his family call home. He and his wife, Blayne, welcomed their son, Hayes, in early 2026, and their family also includes Honey, their much-loved dog.
Jonathan is an avid runner and a believer in continually challenging himself, whether that means logging miles, hitting the sauna and cold plunge, or finding new ways to improve personally and professionally. With plenty of time spent on the road between client appointments, there is usually a podcast or audiobook playing in his car.
Sports have always been a big part of Jonathan’s life as well. He recently spent a season coaching AAU basketball with the 813 Bulls and is an avid fan of UCF, the Pittsburgh Steelers, and the Orlando Magic. Through marriage, he has also learned to lend his support to Florida State when necessary.
Jonathan proudly serves Lakeland, Bartow, Winter Haven, and surrounding Polk County communities, as well as clients throughout Central Florida.