For a low-key date look, one that signals occasion and flare but also carefree low-maintenance, try dressing down a dolled-up look, like a white, ruffled miniskirt paired with lace-up heels. Add a slouchy boyfriend sweater like this one from J.Crew; we love this look with sleeves pushed up just below the elbows. If you're worried about dark brown leather clashing with black, tie the two together by wearing dark, mottled tortoiseshell sunglasses that carry a hint of both. And keep jewelry simple but well chosen, like this rose-gold Vita Fede ring.
Zara leather messenger bag, $99 at Zara; You Can Do It iPhone Case, $35 at Society 6; Schutz Slate Heel, $195 at Piper Lime; Zara White Ruffle Skirt, $60 at Zara; J. Crew Merino Boyfriend Sweater, $88 at J.Crew; Vita Fede Emma Ring, $340 at Shop Bop; TopShop Lab Matt Sunglasses, $36 at Topshop.