If you ever have trouble pairing together items while online shopping, not knowing what looks good with what, then check out the collections on the site you are shopping on! Collections are put together with items that fit into a new style selection that the store is trying to sell. So even if you know what you want, it's good to check out what the collections are so you can see whats in style and what works well together.
One collection I came across and love is the Railroad collection by Topshop. It employs the old 1950s Americana style and they have so really great items in that I would kill for and that work really great together! Check out a few of my favorites and don't be hesitant to check out their other collections and to browse other collections on other sties to learn about some of the in-style items they may be selling!