Stacy says that the most important thing to look for when trying on jeans is the "rise" or crotch area. You don't want any pulling, puckering or extra fabric up front. Also, you will want to make sure your new jeans flatter your booty, hips and thighs—if they're too big in the waist, a simple alteration can make them look custom-made for your figure.
Watch Oprah's jean intervention.
After only seven attempts, Oprah finds her perfect fit in a pair of AG "Club" jeans! "I love these [jeans] because, the crease helps to lengthen," Oprah says. "And even with the cut it's not so low that when you sit, it rises down and you see your crack—that's very important to me."
Stacy also points out that Oprah's jeans are the perfect length. She says jeans should go all the way down to the bottom of your high heel in the back. But, if your aching feet are pleading for a flat shoe, don't you dare roll up your denim. Every woman should have a second pair of jeans that's ideal for flat shoes.