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Writer’s note: This post was first published on Medium’s “Tickled” on July 13, 2019 and will now be permanently housed on Substack’s new “Tickled” column.
My mother loves wearing hats and caps. Up until the summer of 2015, I thought I looked goofy wearing them. But as do all growing women, we start turning into our mothers — fashion included.
I’d recently purchased a fancy hat and thought I was the hottest thing walking. I couldn’t wait to show it off. On my 20-minute walk to the train, I tipped my hat a little to the side. And per usual, I called my mother for our morning phone-commute walk.
I grabbed my cacao smoothie on my way out the door, and off I went. (I drank one almost every morning.) With my smoothie in one hand and my cell phone in the other, I strolled along with my new head attire.

Chicago decided to show off why it’s called the Windy City. The wind started to blow. My hat tilted a little. No worries. I used my index finger to adjust it and continued my phone conversation. Chicago wind blows again. My index finger adjusted the hat a second time.

I happened to see a particularly handsome gentleman walking out of a nearby bank and getting into his car. We made eye contact. I smiled. He smiled. The wind blew a third time.
I then realized that if the Windy City continued to show itself off, this hat would go flying. And underneath my hat was a satin “wrap” cap. (Black women wear these often to protect their hair while sleeping. It also prevents “hat hair” when you take a cap off.) And although Jada Pinkett Smith and Alicia Keys and many other celebrities look fashionable this way, I don’t usually just wear a wrap on its own. I wanted that wrap underneath to stay in place. So I pulled the cap down a third time.
Mr. Handsome was still paying attention to me. And my mother was still talking in one ear. Chicago wind didn’t give a damn about my phone conversation nor this man in front of me, eyeing me as I walked.
Whoosh! The hat slid off my head and onto my neck. I had an instant decision to make. Put down my phone to adjust my hat. Or, put down the smoothie.
Instead I kept talking on my phone with one hand and turned the other hand with a full cup of smoothie to fix the hat. And I felt the almond milk, cacao mix, flaxseeds and banana all slide down my satin wrap cap, my brand new hat, my coat and in the neck of my shirt.
And Mr. Handsome’s jaw dropped. I didn’t know what to say, so I laughed. Hard. By that time, I was closer to Mr. Handsome’s car. He rolled down his window and said, “It’s all good. Whoever you’re on the phone with must’ve been pretty important for you to save your call instead of your clothes.”
At that moment, I remembered why I hate hats so much.
Did you enjoy this post? You’re also welcome to check out my Substack columns “Black Girl In a Doggone World,” “Homegrown Tales,” “I Do See Color,” “Tickled,” “We Need to Talk” and “Window Shopping” too. Subscribe to my free weekly newsletter to keep up with all posts at once.
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