A: Separates are terrific, but random purchases are challenging. Think systematically: To build your wardrobe, you have to know what's already in it. Before each season, try on your clothes and give away anything superfluous, then make a list of what you need. Or go to ClosetCouture.com, a new site that lets you photograph your wardrobe and create (for free!) virtual outfits that you can mix and match. You can even hire an online stylist ($25 and up) to develop personalized looks, packing lists, or shopping strategies.
E-Paper dolls anyone? Test out your wardrobe on a mannequin in the virtual dressing room at ClosetCouture.com and see which combinations work (and which don't).
Chemise, Ann Taylor Loft, $39. Necklace, Roaman's, $20. Dress, Trina Turk, $298. Skirt, Mango, $99. Bag, Cole Haan, $495. Jacket, Rebecca Taylor, $395.