"Daniel and Zelda Barnz, the creators of the show, had written in the script that Chester wears a red tube top to school. I had tried some on him, but after seeing this rainbow crop top on him from Dolls Kill, I felt that it would be a better statement than the red tube top. Also, right now in women's fashion, crop tops are superpopular and Chester would naturally gravitate toward that given his gender-bending inclinations."
Image Source: HBO Max