Day 60 Risk: Wear a Floppy Hat

Gardening anyone?

I love floppy hats. Love love love them. I used to have one years ago but I only wore it once and it fell apart pretty quickly. I occasionally will try these on in stores but for some reason I avoid getting them. Maybe it’s because I think I won’t have any occasion to wear them. Or maybe I don’t want to get one and then never have the balls to don it. Either way I haven’t owned one of these hats in years.

If you remember, the beginning of my weekend was supposed to include a boating trip. I was shopping last week and decided to try to find one for Friday’s boat trip. I searched around and was actually leaving the store when I spotted the above in the gardening section. Normally I would try something on, walk around with it then try it on again, hem and haw and then finally make a decision. I walked over to it, picked it up and said to myself, “Yup. This is mine.” I bought it without hesitation.

Well, due to Chicago crappy weather I did not get to wear the awesomeness on Friday. I decided to test it out on Saturday at our backyard BBQ and was met with a pretty good response. So I wore it all day yesterday, even on the train when we went downtown for a rooftop pool party.

I felt pretty in it and had no qualms about it until we were on the rooftop. A group of people came up after we had been out there for a little while. They seemed pretty young and even though I couldn’t care less what they thought of me, I also couldn’t get the possible judgment they could have been thinking out of my head. Wearing a hat like that is a statement and I’m not always sure if I can really pull off those statements.

But I forced myself to keep the hat on my head and I’ve been around the block enough times to know that while I felt self-conscious, no one probably noticed me. I’m proud though that I didn’t take the hat off, that I wore it with pride. Who cares if the statement works, as long as I feel good in it.

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2 thoughts on “Day 60 Risk: Wear a Floppy Hat

  1. I love floppy hats too, but I feel like a tourist if I wear them around here, lol. Maybe I should take this risk, since I own like 3 of them hahah!

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