Dylan grew up in Indianapolis, Indiana, where he attended Perry Meridian High School.

[1] In the summer of 2014, Windler was selected to play for the Indiana Elite AAU team alongside future Virginia player Kyle Guy.

His performance attracted scholarship offers from 15 Division I schools, and he eventually signed with Belmont.

His following sophomore year, he took on a starting guard position and became an outside threat with a 39.8% three-point completion rate, averaging 9.2 points per game.

Coming into his senior season, Windler was named to the 2019 Julius Erving Award Watch List.

[9] He made his NBA debut on December 23, 2020, recording three points and two steals in a 121–114 win over the Charlotte Hornets.

[18] On January 6, 2024, Windler signed a two-way contract with the Los Angeles Lakers.

[9] On August 23, 2024, Windler signed with the Perth Wildcats of the Australian National Basketball League (NBL) for the 2024–25 season.

[22] Winder's wife Lauren gave birth to the couple's first child in December 2024 in Perth, Australia.