It's rare that I wear an entire outfit more than once, let alone one that is seemingly as "simple" as this one. I have this need to keep mixing things up, rotating my favorite pieces while making them feel fresh and new. However, this particular look is on repeat. Aside from the fact that it fits into my NYC uniform requirements very well, it's a class ensemble that transitions easily from office to cocktails. The best part? When running between meetings, shows and lunches in downtown NYC my stacked heel boots save my life and ensure that I don't go stumbling on the rickety cobblestones that I love so much.

Get the look:

Pleated leather skirt (Score it for less than $70!) || Oversize cropped turtleneck || Zara Boots, old, similar here and here || Michael Kors Men's watch || Kendra Scott Ring || Celine Luggage Tote || Elizabeth & James Sunnies

Beauty details:

Blowout extender || 3.1 Phillip Lim for NARS polish || Lips

{Photography by Matthew Perrone}