Happy feet are usually dressed in softer, more pliable leather. "It has memory—it molds to the foot," says Gordon Thompson III, creative director of Cole Haan. Well-made shoes also have flexible leather soles.
No-show construction is important: The better crafted a shoe is, the more seamless it should look, with no visible glue or staples.
Less weight often correlates with greater quality. Heavier shoes (other than work boots) signal bulkier, less refined components.
Unfinished insides aren't comfortable, no matter how cute the outside. A leather lining is best because it absorbs excess moisture and has enough "give" to allow the foot to swell slightly.
High heels can feel wobbly if they're very thin at the top, where they're attached to the sole. Wedges and chunkier heels are more stable because weight is distributed over a wider area.
Buying too tight—and hoping the fit will ease up over time—is the number one mistake people make. "If a shoe pinches, no amount of stretching will make it comfortable," says shoe designer Patricia Green.
Buying too high is another problem, says Thompson: "Women often wear heels that they can't comfortably walk in."
Buying too short is an issue with sandals: The foot should sit squarely on the sole of the shoe, with no toe spillover.
Pictured above: Rich and thin is a powerful combination. Shock the office (pleasantly) with these jewel-tone patent leather stilettos (Manolo Blahnik, $575).