I always thought that wearing hats was such a big deal. Like it was one of those fashion risks that you weren't sure would pay off or not. Especially at school, I thought that it might be a bit too bold. I had waded into the pool with slouchy beret style hats a few years back, but I always adored the look of a real hat. One of my friends wears hats quite often to school and I have realized it is not that strange! However if you are still on the edge, try out a thick headband or a big bow to get started.
Many people would say they use hats as an shield to a bad hair day. If you were to ask me, I think it is very important your hair goes somewhat with your head piece. I would never really just throw a hat on a walk out the door. My best advice to deciding what kind of hair goes with your hat isn't very straightforward but will pay off. Start off before doing anything, like heat styling etcetera, to your hair and just put the hat on. Survey how it looks and then go from there. Find if you prefer straight locks or curls and waves. But my biggest advice is make it manageable. I normally find it necessary to have to readjust my hair after awhile of wearing a hat. So, if you have that issue in common with me, make sure the hair style you are sporting allows for a quick, as I would call it, 'phloof'-ing to liven up limp pieces.
Another fun play of the standard hat is something like a "hat on a stick." Really only acceptable for a party in my opinion, you can find little bitty hats with other fun add on's attached to a head band at lots of stores. I think it would be really fun to DIY one with friends for some sort of costume party!
Right now I love big floppy brimmed hats! Even though they remind me of summer somewhat, the burnt orange, black and navy shades scream winter. What is your favorite type of hat? How do you like to wear it? Let me know in the comments below!