By Lisa @Privilege

We’ve addressed workwear on Privilege, several times. We’ve explored festive occasions that require little black dresses, or designer confections. But some of us require a more relaxed elegance. We wonder, how to dress when retired, or working from home, or, fleeing our suburban haunts for the big city? In other words, what kind of wardrobe is comfortable and without ceremony, but still stylish?

One might well ask. This is my most current and central fashion quest. At my nadir, pressed for time after a brisk neighborhood walk, I entered Whole Foods wearing baggy white basketball shorts, sports bra, white tee printed with Microsoft marketing gibberish c. 1998, and Mizuna walking shoes in pink, white, and silver. We will pause as you guffaw. Urgency is the best teacher.... More...