There are certain outfits that I have no qualms about wearing over and over (and over) again. This would be one of them. Its endless (and shameless) wearability is anchored in a combination of classics and a little print mixing. And it's easy to re-create with these J.Crew leather pants (or these J Brands that are 30% off or this $100 faux leather pair by Michael Kors), this striped sweater by Kule or Pam & Gela, this Clare V. animal print clutch, and these black flats by Vince, Jenni Kayne or 3.1 Phillip Lim.
P.S. Speaking of classic pieces that are over and over again wearable, this $39 Joe Fresh cropped denim (Chanel-like) jacket qualifies and then some. Though you can't buy it online in the US (Canada only right now), you can call a store and they will ship it to you free. Nice!
Photo: Death by Elocution