For drinks at that new rooftop bar, add bright earrings, a shiny clutch (extra cool if it's oversize) and a tank top or a crop top, if you're feeling a little more adventurous. You'll look fun and cool and confident, and girls in the bathroom line won't be able to disguise their outfit envy.
For a fancy cocktail party, pick varying shades of red and wear the color head-to-toe. It's a sleek, stylized look we could totally see some risk-taking-but-elegant fashion darling wearing. (Zoe Saldana, perhaps?)
For weekend brunch with your most fashion-y friend, anchor it with a heel that's blocky and easy to walk in, because you know, it's brunch. Then add slightly silly sunglasses, a printed bag and one of your favorite weekends-only t-shirts. If there were street style paparazzi outside the restaurant, they'd stalk you.
For work, tone down the skirt's look-at-me-ness by pairing it with conservative black and white pieces. (Maybe carry your usual classic black tote during the day, but tuck a printed one inside so you can transition your outfit to drinks afterwards.)
For a party, pair it with an equally punchy printed top and cinch the outfit together with a bright neon belt that picks up one of the accent colors from the top. It'll make it feel cohesive, like you hired a Hollywood stylist to pay attention to those little details.