The random number generator kicked out the number 35 for the first challenge in our chain, and #35 on the list is deb.

I was absolutely stunned, in looking at some of deb's past posts, to discover that she recently turned 60. Based on your photos, deb, I would have guessed early 40s. Since I'll turn 50 this year, I'm sure we share some of the same issues around dressing in middle age: how to look current without looking silly or faddish; how to look relevant and in-tune without trying to look like a teen; how to dress a body that's plagued by various age- and health-related issues such as really, really fussy feet.

One of the most helpful guides to me in this process has been one recommended by Angie years ago, Style Evolution by Kendall Farr:

My challenge to you, deb, is to go to this book's page on Amazon and click the "Look Inside" link on the book cover. Once you're in, click on "Surprise Me!" (it's the last item under "Book Sections" on the left). Your challenge is to devise an outfit inspired by something on whatever page of the book comes up.

Because some of the book is about body shapes, you might land on something that just doesn't apply to you. That's fine -- I'll modify the challenge by saying you can click the Surprise Me! button up to three times and choose the page that most inspires you of the three.

How does that sound?

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