Wear what you love wearing. Simple as that. If your change in wardrobe does not feel right, it will show all over your face. If wearing the dresses and skirts makes you feel good, wear them. That, too will show all over your face. Be real and genuine to who you are. I am having a love affair with boots, skirts and dresses lately. I know my husband enjoys wearing jeans when he does not have to wear slacks for work. The way I make it work when we go out is my jeans are very dark and I wear heels or boots with them. I also put on a top that makes me feel good. 

You know how to work it, V! Just do your thing.