Best Bet: Chrissy Sweater


A slouchy, sweatshirt-like top in heather gray tends to pair well with more formal bottoms (leather pants or a silk skirt, say) — casually cool in a not-trying-too-hard way. This sweater's longer length and drapey cut give it a feminine, rather than athletic, look, and the pocket detail differentiates it from similar styles. Plus, the under-$100 price tag beats the replicas of designs seen on the runways over the last few seasons.

Jack by BB Dakota Chrissy Sweater in Heather Gray, $61 online.