Here are my tips on which hat to wear with what types of outfits and various weather situations:
Cloche Hats: Wear with sleek, structured trench coats and fitted coats and jackets in chilly but not-too-cold fall weather. Cloche hats look retro chic with a fine gauge knit sweaters and sweater dresses and crisp classic clothing styles. Think Ralph Lauren style clothes.
Chunky Knit Hats: Wear with sleek, structured trench coats and fitted jackets in chilly but not-too-cold fall weather. OR wear these with ultra casual, bohemian fall and winter looks. Think Olsen Twins with huge chunky scarves piled on in the winter. Either way, I love the versatility of chunky knit hats and their ability to transition from chilly fall to the freezing dead of winter.
Sleek Knit Hats: Wear with sleek, structured trench coats and fitted jackets in chilly but not too cold fall weather. Also, wear with casual looks as well but I wouldn't recommend these in hardcore freezing weather since they are usually thin and not meant to be super warm.
Fur Hats: Wear with nylon puffer jackets and bulkier cable knit wool, wool blend, cashmere or alpaca sweaters and corduroy, velvet, tweed, boucle jackets and coats, pants, shorts and skirts. The fur lends an opulent look to plush, cozy fabrics. Wear these in the dead of winter when it'd freezing and you when you have to be outside A LOT.
Note: These are not fashion rules that are written in stone. They are just suggestions and ideas on what hats to wear depending on the scale of your outfits and coats. These happen to be what I prefer. But definitely wear what you like and how you like it. Whatever you choose, stay warm and stylish! :-)
