Start by familiarizing yourself with what she's already wearing to get clued in to colors and styles she prefers. You'll also need to know her size or measurements. Items that come in small to large (sweaters, track suits, etc.) will be easier to fit than exact numbers (like a size 8 trouser). Make sure you can exchange the gift and hold onto the receipt. Here's how to navigate women's wear:
Sizes
Four different size ranges designate a specific fit in the United States: juniors (odd numbers from 0-13 fit a youthful figure), missy (even numbers 2-14 have more generous hips and bust), plus (even numbers 14 and up for missy fit; odd numbers 15 and up for junior plus), and petite (even numbers in missy and plus to fit women under 5'4"). There are no standardized sizes in womenswear.
Looks
Casual style is typified by denim and sporty influces; it works best for weekend wear or stay-at-home moms. Classic style is a polished, chic look that relies on good quality separates that can mix and match (blazers, slacks, blouses). Contemporary style is a trendy look that captures the latest fashions. All three looks are ageless and most women cross-shop categories for their wardrobes.
Flattering styles
Simple cuts look great on everyone; the more bells and whistles the outfit comes with (embellishment, layers, belts, etc.) the more difficult fit and flattery become. Dark colors (navy, charcoal, black) are slimming. Vnecks and turtlenecks call attention to the face; well-cut trousers or mid-calf skirts can hide heavy legs.
Fabric
Classic styles call for better natural fabrics such as wool and cashmere (often dry clean only); sporty casual styles are often made up in denim or hi-tech manmade fibers (usually all machine washable). If possible, touch the fabric (the way the fabric feels -- the "hand" -- is an integral part of a garment's appeal).
Labels
Most stores carry a variety of manufacturers and price points. Some stores like the Gap or Old Navy carry only merchandise that is made specifically for their store. Designer labels (Ralph Lauren, Donna Karan, Calvin Klein) usually start in the mid-hundreds. Secondary lines of the designers (Lauren, Polo, CK Jeans, DKNY) are often very reasonable in comparison (usually around $50 for jeans).
Shortcuts
Ask her to use the "Wish List" option provided on many sites (Amazon.com, Nordstrom.com). Take advantage of online stores' live online help. When in doubt, choose a gift certificate (sure to fit!)