I have grown to love more versatile pieces in my wardrobe that can transition from day to night, and even classic pieces that span seasons. I often get accused of only wearing something once, when that is never the case. I like to challenge myself to not wear the same thing the same way twice. It doesn't always happen of course (rarely ever does) but it's fun to challenge myself to think of something in a new way for a different day. It makes me feel like I am getting more bang for my buck when I figure out new ways to wear something. I love taking something sophisticated on its own, like the black dress and sassing it up with a well cut jacket in unexpected materials/color combinations for a more formal occasion. Unexpected items bring out your own style without being over the top. If items can go for a multiple looks, that is always a plus in my book. Jackets do this a little easier though. I think the ever-popular "Creme de la Creme" sweatshirt paired with rugged jeans and a shoe pop of pattern is a fun alternative to just a casual sweatshirt and jeans. It's a nice look for brunch with girlfriends but can go into an evening out as well. Versatility is your friend. Expand your wardrobe with what you have.