Transitional dressing can take many forms, but when summer melts into fall, a flirty sundress is still on point. We love a sophisticated print in autumn-appropriate tones, and this poplin maxi dress by Cara Cara is a stand-out choice. Lest we forget, it’s about to be sweater season, so pair your floral frock with a preppy cardigan when the temperature drops. Helmut Lang’s fiery red sweater boasts oversized lapels and a cropped silhouette for a balanced effect. Aquazurra’s Twist 95 sandals imbue this look with instant poise, especially when paired with elegant pearls and an iconic quilted handbag.