Kanye West's Monster Fashion

With 808s & Heartbreak, West made an unexpectedly sorrowful and poignant statement about loss, love unrequited, maturity, and compromise – in other words, it was his true bildungsroman, set to poetically sparse polyrhythms. To suit his newly sober and grown up visage, Kanye constructed an appropriately sophisticated and demure look. Incidentally, his gray checked suit, spectacles, and customized Marc Jacobs heartbreak pin have gone onto become arguably his most iconic  – and perpetuating – style statement to date, proving displays of sincerity and simplicity can immortalize an icon's image as much as shock and awe.