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“Aren’t you the cutest dog?” I asked the chubby brindle pit bull mix walking down the sidewalk.

Objectively, she was not the cutest dog, I suppose. But there is no such thing as an ugly dog, as we all know. She was wearing a brand-new jacket with colorful pockets and a hood and, to top it off, had matching booties. She looked a little self-conscious — as we all are when we get dressed up for the first time in a while — and I thought she could use a little reassurance.

“I wasn’t sure she would wear the booties,” her owner confessed.

The dog looked at me seriously, as if s...