Hats make you look cool. Seriously.

I know a lot of people who say that they aren't "hat people." Hell, I used to be one of them. Hats have definitely lost a lot of their cachet in the past few decades, moving from an element of style that was all but legally required to be a part of polite society to something that is only worn by the uniquely stylish or the uniquely douchey.
Well, good news, everybody - you too can be uniquely stylish! Or at least make other people think that you are.
My journey into hattedness started pretty recently, when Brian gave me a 1960s black pillbox hat for Christmas to go with a baby blue swing coat from the same era (any guy who buys you accessories is a keeper). It was a serious lid, and though I loved it, I had some concerns. It looked good on me, but how the hell was I going to keep it on my head? And what if people laughed at me?
Well, no one did that. In fact, people were stopping me on the street to tell me how much they loved my hat. And keeping it on is actually really simple - hat pins. I'll go into more detail below.
A well chosen hat has a way of elevating an outfit. I'm not talking your standard baseball cap or fedora - there are hundreds of unique styles out there, and chances are if you spend a little time trying them on, you will find one that works for you. They don't have to be expensive either. I've accumulated quite a few hats now, and I haven't paid more than $50 for any of them.
hat collage
Clockwise from top left: Beaded hat, $18; yellow hat, $16; sweater that I tied around my head after dying my hair, free; straw hat, $12 
I tried to come up with some tips for finding the right hat, but honestly, it just comes down to one thing - spend some time playing around with them. You honestly never know what will look good on you until you put it on your head. I once tried on a hat that consisted of straps of felt, a ball of fur, and a veil. On the table, it was pure WTF-ery; on my head, it was fabulous. I passed it by, only to be sad when I came back to find someone else had bought it.
So, hat pins.
Hat pins are great, but you do have to be kind of careful with them. Stabbing yourself in the head isn't fun. What you want to do is put them through the hat and underneath a section of your hair, which is what anchors it to your head. It is helpful to take the style of hat into consideration when you're doing your hair - the taller the hat, the more volume you'll want. If you're not teasing or curling your hair, figure out where you want to put the hat pin and put a couple of criss-crossed bobby pins in your hair there. Thread the hat pin underneath that, and it'll hold it on place nicely.
I only have a couple of hat pins, but I'd like to acquire more in the future. When not in use holding your hat in place, they make excellent little brooches as well.