In Memory of Jessie Lester: Family Support

In Loving Memory of Jessie Lee Lester

October 20th, 1982 - September 30th, 2025

It is with great sorrow that we announce the passing of Jessie Lester, 42, of Lakes Wales, Florida. He departed peacefully on Tuesday, September 30th, 2025, surrounded by his loving family.

Jessie was born to Dennis and Mary Lee Lester on October 20th, 1982, in Pahokee, Florida. He was a beloved son, brother, spouse, father, and a favorite uncle and friend to many.

He became a licensed barber in 2009 but had mastered his skills long before that. Jessie started at the young age of 14, stealing his father’s clippers and cutting his friends' hair, and effortlessly developed a talent. He was well established in many shops across Central Florida, including Faded Fresh and The Lab in Lakes Wales, The Man Cave in Haines City, and his current place of work, Stay Faded Studio in Sebring. He was known for his uplifting energy, his infectious laugh, and most importantly, his sympathetic personality of always being able to connect with people, no matter who sat down in his chair. Those who knew him will also remember him cruising in style on his Harley Davidson and dressed to impress.

Jessie was an avid outdoorsman who grew up in South Florida bass fishing, diving in the Florida Keys, and riding four-wheelers. He was an enthusiastic golfer, often causing laughter and chaos on the greens, while his beloved dogs tagged along. He lived life largely, had the biggest heart, and always believed in the best of people, no matter their mishaps.

He is survived by his beloved father, Dennis Lester; the love of his life, Eufemia ‘Monica’ Dimas; and her three children, Yarelli Osorio (21), David Osorio (20), Katherine Nicole Gonzalez (12), and the whole Dimas family. His life lives on through his daughter, Jaliyah Celeste (21), and her newborn, Taylin. His memories will be forever cherished by the mother who raised him, Penny Lester, and his siblings, Shawn Lyn, Bryan Moses, and Shawnee Taylor.

He was preceded in death by his grandparents, Sally Vance, Grannie G and James, and his mother, Mary Lee Lester.

A Celebration of Life service will be held on Sunday, October 12th, 2025, from 3-6 PM at the Bonnet Springs Park Event Center in Lakeland, Florida.

In lieu of flowers, please contact Hobby Hill Florist at [phone redacted] in Sebring. The family requests that any donations be made to their GoFundMe.

Jessie will be dearly missed by all who knew and loved him.