20. Scott Disick
Whether you love to hate him or just hate him, you can't deny that Scott Disick dresses like a boss. What we're not so sure about is whether his assholeness fuels his swagger, or if his swagger fuels his assholeness? Whichever it is, it's a self-perpetuating machine that is necessary when you're basically fam with 'Ye. After earning Kanye's praise for his Astor & Black bespoke suits last year, Disick has taken on the quintessential Kardashian quality: we're not sure why he's relevant, but at least he looks good and dressed well while on camera.