Add some color, some denim, and some sort of accessory that looks like a cool flea market find, like kitschy sunglasses or a bag in a wonderfully unnecessary print. Then go picnic-ing or dancing at an outdoor concert or do something fun.
White & black colorblocking is an easy way to borrow a bit of Céline-y sleekness. Throw this together for drinks somewhere too cool for its own good, and you'll look like the new wave of models-off-duty.
drawstring dress, $59.99, zara.com; addict extreme lipstick in "fireworks 756", $31, dior, sephora.com; perforated leather sleeve bomber jacket, $299, jet by john eshaya, intermixonline.com; leather ankle strap sandals, $79.99, mango.com
Toss some nautical stripes over and wear it like a skirt; then mix in some other Cape Cod-y staples like monogram jewelry and a straw tote. You'll be the best dressed person in the entire preppy beach town (or in a landlocked state, whatever.)
Play with bright, glittery acessories and splashy makeup shades you don't get to bust out that often in winter. It'll make a rooftop party even more fun.
drawstring dress, $59.99, zara.com; "barbados" large stud earrings, $55, noir jewelry, shopbop.com; marvelous moxie lipstick in "risk it all", $18, bare minerals, sephora.coml "azealia" glitter-finished leather clutch, $595, sophia webster, netaporter.com; "labrea" asymmetrical sandals, $105, b brian atwood, shopbop.com
Keep the white going head-to-toe for a look that'll easily slide from day to drinks—even in those ridiculously comfy flat sandals—because it reads so stylized. (Just add some smudgey eyeliner to give it a bit of swagger.)