The Courage to Wear A Hat

It takes courage to wear a hat. Don’t let anyone tell you otherwise. A baseball cap is easy. Every one – male or female – looks good in a baseball cap. So I’ve got no special admiration for people who sport baseball caps. It’s fine. It’s cool. It’s a little wee statement. You’re a Packers fan or a cancer survivor or maybe a survivor of one of those incredible cancer charity walks. So a baseball cap is cute and maybe a tad informative, but requires little by way of chutzpah.

A real hat – like a fedora or a big sun hat – is a different matter. Before I transitioned into the hat-wearing world, I’d buy hats, hang hats on hooks on my bedroom wall, put a hat on, walk around the house in it, catch my image in a couple of mirrors and hang the hat back up. I’m just not ready, I thought. I don’t have what it takes to wear a hat. And, in the weird words of somebody in reference to a woman wearing something radical or different, I thought I just ‘couldn’t pull it off.’ Maybe someone else could but I just don’t have what it takes.

A few years ago, after my dermatologist started carving small slices of skin cancer out of my face, it occurred to me that it would be a good time to get over my hat anxiety. It was just time to put a hat on, admire myself in the mirror, and walk out the front door with the hat still on my head. So I did. Every time I caught myself reaching up to fling off the hat, I remembered the doctor’s tiny scalpel and left it on.

Last week, I put on my new hat, a big sun hat, a lovely and very stylish and somewhat expensive hat that I bought in a small shop on Coronado Island. It has a wide brown brim, fabric, very floppy with a lovely stitched trim. I love this hat. So I wore the hat to drive across town in my convertible. I got in, looked in the rear view mirror and thought, ‘this is so Driving Miss Daisy.’ Seriously, you are really going to drive through downtown Milwaukee with the top down wearing this hat?

Yes, ma’am, that’s exactly what I’m going to do. Because I like the hat.

And I no longer give a shit what anyone thinks about my hat. Ultimately, that is where the courage to wear a hat comes from. Not giving a shit about what other people think about your hat.

It’s very freeing. You should try it. Have a hat on me.