Expectation: You show up for date-night and look like a total knockout (without putting in any effort, of course). Reality: You spent hours grooming pesky fly-aways, turning your bedroom floor into a mini war zone of discarded outfit options, and reapplying your cat-eye three times because you couldn't get the flick just right. And we're right there with you.But sometimes less effort equals a cooler look (imagine that!), and your favorite wardrobe essential has something to do with it. We're talking about denim — the perfect foundation for a slew of ensembles that instantly read: Oh, this outfit? I just threw it on. You might overlook the staple because of its casual vibe, but with the right accoutrements, jean pieces can give your outfit the understated finish it needs. See how we worked the latest denim styles from Macy's into looks that work for every type of date, below, and soon enough the expectation vs. reality struggle will be a thing of the past.Whether you're checking out an exhibit or getting schooled in a wine class, you'll want a chameleonic look that can go with the flow of the evening — you know, in case you two hit it off and a "have you eaten yet?" is thrown out there. Start with always-chic stripes paired with a tailored trouser in an eye-catching color. Sleek and shiny booties are easy to walk in and elevated, while a distressed denim jacket thrown over your shoulders gives the look a carefree, down-for-anything vibe.