The hat is one of the best accessories a woman can wear. From a classic fedora, to boater or cloche style, there are so many choices! It can be a little tricky but here are few tips to help you out:
1. Ask yourself if the weather is suitable for the style of the hat you wanna wear. If it's too windy you usually end up seeing nothing through the floppy ones and also if the hat is just sitting on your head and it's not fitted you can end up without it (like I usually do haha, most of the time I decide to wear a hat I end up holding it in my hand because of the London's windy weather). So the point one is also including a right fit!
2. What is your hair length? For example, a close-fitting cloche may look better with shorter hair while floppy styles may be better suited to longer hair styles. But it really depends on the individual style at the end of the day anyway.
3. Hair style? I find it always the easiest to wear my hair down, some curls look good as well, also a loose side braid is cute :). Wearing your hair in the ponytail is not so good for the look or I guess the hat would not fit properly if your hair is up either.
4. Colour of the hat? Black is the classic, of course. Grey, tan and camel colours are easy to match nearly any outfit. But if you want to make a statement go for a bright bold colours! (I was so lucky with this one, it only cost me £5 from Rokit :P)
5. And what to wear with a hat? Anything! It really depends on what kind of style of hat you're going for! A felt fedora will generally go with a range of outfits. The floppy ones are a little more feminine so think about dresses, tight skirts etc. Most of the time I wear my hats, I match them with my "western" boots (see in this post as well) as I think they compliment each other very well :).