Vests are adorable, but I usually feel so silly in them! I had great, random luck with a vest last winter, so I think my vest strike is officially over, though. In fact, a moto vest was at the top of my fall shopping list. I wear my black leather jacket more than anything else in my closet, and having a vest version gives me even more versatility. For my first look, I paired it with old cargo skinnies that are back in style this year. (I tried on the H&M pair below and can attest that they fit SO WELL, highly recommend those if you're looking for a pair!) I also highly recommend the vest - it's the very first one I ordered/tried on and it turned out to be the perfect fit. My vest luck continues. May the vest luck also be with you.
Vest: ModCloth c/o, $60
Top: H&M, $19 (worn inside out) (similar)
Pants: AF c/o, old (similar below)
Shoes: Saks Fifth Avenue c/o, $70 (similar, lower)
Purse: Michael Kors/Macy's, $270 (similar)
Necklaces: My Stella & Dot One, Two
Approx. dates: Pants and purse are 4 years ago. Top is 1 year ago. Shoes are recent. Vest is new.