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After graduating from high school, Winslow entered the Juilliard Theater School in New York, where he received a fundamental education in acting. During his academic years, he actively participated in theatrical productions and various projects, which helped him develop his acting skills.

His cinematic debut took place in the early 2010s, when he received small roles in independent films and television series. Over time, his talent and professionalism attracted the attention of directors, and he began to receive offers from major studios.

Some of the more famous films and TV series that Winslow Fegley starred in include:

- "New York City Stories" (2017): In this drama series, he played one of the key roles, attracting the attention of viewers with his talent and emotional depth.

- "The Next Step" (2019): In this youth series, he embodied the image of a talented dancer, demonstrating his acting and choreographic abilities.

- "Crime Notes" (2021): In this crime drama, he played the role of a young detective, receiving critical acclaim for his outstanding performance.

Winslow Fegley continues his creative development and work on new projects that help him discover his talent and inspire his fans. His name is becoming more recognizable and respected in the cinematic world, and his talent makes him one of the most promising young actors of our time.