Honestly I think she always looks great but the moments that stand out for me are definitely the pre erotica to erotica era (up until she had that fuckass pixie cut which kinda ruined everything) and the rebel heart to beginning of the trump administration in 2017
Yes, Gwen Stefani, Donatella Versace, Julia Fox, Linda Evangelista, Katy Perry, Rosie, Michelle Visage, Andy Cohen, Eva Herzigova.. So many names and as I said it shows how many people in the industry love Madonna and respect her