Unless you're rich and famous, it's neither practical nor affordable to wear brand new clothes everyday. Actually, scrap that, because even celebrities have certain items they wear on repeat, falling back on their signature styles in times of sartorial uncertainty. 

The key, of course, is to ensure the shoes or garment you want to wear time and again are versatile and can be styled up in multiple ways. Just take a look at Harry Styles, Russell Brand and the high swaglord himself, Kanye West, all of whom are guilty of wearing the same footwear on more than one occasion, but know how to style them up in ways that keep 'em looking fresh.