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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.