off the cuff

Here are a few tips for managing a major style transition without going bankrupt/insane.

Dear Winona,

"While ample cleavage comes in handy for filling out sundresses and storing cracker crumbs for later, it presents a professional dressing challenge that’s annoying and a little unfair ... "

I’ve always hated shopping for dresses in general (I’m seriously supposed to track down one garment that fits properly on my chest, waist, arms, and hips simultaneously?), and finding the right thing to wear to a wedding is always tricky (do they really mean casual?).

Dear Winona,

"Your quest to stay true to your retro aesthetic is not impossible. Here are a few tips for incorporating your love of vintage into a modern, casual wardrobe."

Dear Winona, I’m addicted to black. Exhibit A: my closet. Am I fashionably lazy? Or is it because it just goes with everything—mainly me?

Our fierce fashion ace Winona Rose helps our editor Katie Tandy avoid the purgatory of endless Old Navy trousers.