Gettin' the Boot

Well, the weather started getting cooler and I knew that meant it was time to put away my dirty flip flops and bring out my one pair of winter shoes—the tall black boots. I’m counting on them lasting me another season even though the heel is about to fall off of one of them.

So the other night before a dinner engagement I went to put them on. But wait. Something wasn’t right. It was a conflict of fashion interest:

The new straight-legged-skinny jeans can’t accommodate tall boots. I tried with all my might to fit the jeans over the boots but in the end I looked like I had really low, wide knees.

But then I glanced at my Jess Weekly and realized that boots don’t HAVE to go under your jeans, they can go OVER your jeans!

Did I like this look? I called in reinforcements:

Tips from Thea said over email that maybe I could “pull it off.”
Shoe Princess Liz wrote that maybe I could “see if it works.”

Hello? I wear dirty flip flops and pajama pants all day! I don’t know how to pull things off or make things work! I asked Liz, “How do I know if it’s working?”

She did what any fashion expert would do. She asked for a visual aid. I quickly struck a pose and sent her this:

She admitted that she originally was hesitant about the idea but after seeing my ensemble she thought I could, in fact, make it work. When I arrived at the dinner my fellow diners agreed. (Although they didn’t have much of a choice; there was no turning back by then.)

And even though I think I sort of looked like I was wearing galoshes, I’m pleased that I took such a fashion risk and that I may have “made it work.”

But dirty flip flops, hang in there. Just four short months and we can be together again.