Winslow was born into a family of actors: he is the son of actors Michael Fegley and Merce Tonne, and brother to actors August Fegley and Oakes Fegley.

Winslow developed his skills in 2017 while starring in the stage production of A Billion Nights on Earth, a production he also added creative collaboration to, with avant-garde theatre director Thaddeus Phillips. The show was developed at the Buntport Theatre in Denver, CO, over the summer of 2017, then toured to sold out houses in Philadelphia in September 2017, and was featured as part of the Next Wave Festival at the Brooklyn Academy of Music in November that year, where it again sold out its run.

In 2018 Winslow landed his first television role, guest-starring on the hilarious TV-Land show Teachers. He then spent the spring filming 8 episodes of the Disney Channel series Fast Layne, as Mel (which debuted in 2019). After wrapping up on the limited series, he went directly into production in the title role of Timmy Failure: Mistakes Were Made directed by Academy Award-winner Tom McCarthy. It premiered at the Sundance Film Festival and then debuted in early 2020 as one of the first original features for the Disney+ streaming platform.

In the fall of 2018 Winslow co-starred in the Jacob Chase-helmed horror film Come Play, opposite Azhy Robertson and Gillian Jacobs (released fall 2020).

In 2019, he guest-starred as a preteen Sean in ABC's hit show The Good Doctor.

In the final months of 2020, Winslow returned to work filming Nightbooks, starring as Alex opposite Kristen Ritter and Lydia Jewett. The David Yarovesky-directed picture debuted in the Netflix Top 10 in the fall of 2021.

In the beginning of 2021, Winslow starred as Jake Doyle in what would be the HBO Max 2021 holiday hit 8-Bit Christmas with Neal Patrick Harris, Steve Zahn, and June Diane Raphael.

温斯洛出生于一个演员家庭：他是演员迈克尔·费格利和梅尔斯·托恩的儿子，也是演员奥古斯特·费格利和奥克斯·费格利的兄弟。

温斯洛在2017年主演舞台剧《地球上的十亿个夜晚》时发展了自己的技能，他还与前卫戏剧导演撒迪厄斯·菲利普斯（Thaddeus Phillips）进行了创造性的合作。该节目于 2017 年夏天在科罗拉多州丹佛市的邦特波特剧院开发，然后于 2017 年 9 月在费城巡回演出，售罄，并于同年 11 月作为布鲁克林音乐学院 Next Wave 音乐节的一部分亮相，再次售罄。

2018 年，温斯洛获得了他的第一个电视角色，客串出演了热闹的 TV-Land 节目 Teachers。然后，他在春季拍摄了迪士尼频道系列剧《Fast Layne》的 8 集，饰演梅尔（于 2019 年首次亮相）。在完成这部限定剧集后，他直接投入制作，出演了由奥斯卡金像奖得主汤姆·麦卡锡执导的《蒂米·失败：犯了错误》。它在圣丹斯电影节上首映，然后于 2020 年初首次亮相，成为 Disney+ 流媒体平台的首批原创功能之一。

2018 年秋天，温斯洛共同主演了雅各布·蔡斯执导的恐怖片《来玩吧》，与阿兹·罗伯逊和吉莉安·雅各布斯（2020 年秋季上映）演对手戏。

2019 年，他在 ABC 的热门节目《好医生》中客串出演青春期前的肖恩。

在 2020 年的最后几个月，温斯洛重返拍摄《夜书》，饰演亚历克斯，与克里斯汀·里特和莉迪亚·朱维特演对手戏。这部由大卫·亚罗维斯基执导的电影于 2021 年秋季在 Netflix 前 10 名中首次亮相。

2021 年初，温斯洛与尼尔·帕特里克·哈里斯、史蒂夫·赞恩和琼·黛安·拉斐尔一起出演了 HBO Max 2021 年假日热门剧集《8 位圣诞节》，饰演杰克·道尔。