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A: Not by reaching automatically for worn-out pink sweatpants! I know: After five days in pencil skirts and pumps, you want to collapse into elastic waists and running shoes. But a few no-fail, no-brainer weekend outfits—that aren't too businesslike or too schlumpy—will serve you better. Don't go the oversize route. Body-skimming shapes are always more attractive than baggy.
Also, avoid black, with its formal connotations. Pastels are much better (but not head to toe—too Easter Bunny); so are pale neutrals like khaki, sand, and dusty rose.
Buying a whole separate Saturday-to-Sunday wardrobe isn't necessary. I say stock up on basics—dark jeans, nicely fitting khakis or corduroys, cute cotton sweaters, stylish T-shirts, a casual jacket. Then mix them with more office-y pieces, either current staples or former weekday standbys recycled for weekend use. With flat shoes and less-polished accessories, even pinstripes can look casual. In short, make an effort. Next time you bump into an ex at the supermarket, you'll be glad you did.
From the May 2008 issue of O, The Oprah Magazine
