When I start feeling a chill in the air I know it's time to start breaking out all my favorite cooler weather pieces and pile them on. Any black down jacket that will smush into a small ball works for me and a gray hoodie is a no brainier. I'm all about a pair of black leggings that can be worn to the gym (ones made for working out usually last longer and feel better on than other types) and also be paired with boots for a night out - especially handy when you travel a lot like I do. Sometimes it's good to add a pop of color where you least expect it, in this case, a sports bra that will lightly show through that white tee. And there is nothing like wearing bad ass sunglasses, some retro sneakers and a beanie to edge things up a bit.