If you have a round, short face, the top of your hat should be round and short. If you have a long, thin face, then the crown of your hat should be similarly shaped. You ladies, now, have a lot more leeway on hats, because your hair's usually bigger. Heck, you can even get by with some of the pastel varieties without unduly raising eyebrows. With pants, now, you have to be a bit more careful.
Boots are a nice addition, and again, the ladies have a broader choice than the gents.
They can get by with the highly decorated footgear in teal and puce and seafoam green. You could be in for a wild ride.