IMO the coolest looks by an artist or artists are the following:

1. Prince (Purple Rain era, Diamonds and Pearls era, Parade/Under The Cherry Moon era and 3121 era)

2. Elvis (70's era)

3. David Bowie (Ziggy Stardust era)

4. Elton John (70's era)

5. Motley Crue (80's era)

6. Michael Jackson (Thriller era)

7. Madonna (Like A Virgin era, True Blue era and Vogue Era)

8. Frank Sinatra (60's era)

9. James Brown (80's era)

10. Run DMC (80s era)

Now I know image is not everything but fortunately or unfortunately it counts in the music world and some artists like the ones I listed above just makes you wanna go out and buy exactly what they have on!! at least it makes me feel that way lol anyways what are your 10 favorite looks by an artist or artists? List them below!