INVEST IN NEW KNITS

What better way to welcome the newly crisp air than with a neutral knit that’s cozy enough to curl up on the couch in yet still cute enough to venture outside in. We particularly love this taupe set from By Malene Birger: The longline top has elegant wide sleeves, the rounded pants taper neatly toward the hem, and it’s all done in a fine, soft blend of wool and yak hair. Pair it with smoothing foundational pieces for a clean-lined silhouette.

STRETCH YOUR SUMMER PRINTS

Some simple styling choices can afford your summer-leaning prints a second act as temperatures drop. Opt for dark-hued plus-ones—sleek black Chelsea boots, a slouchy navy knit, or a simple clutch in soft black lambskin—to set a moody tone that feels appropriate for the new season.

CIAO LUCIA DRESS, goop, $450

FIND YOUR PROPER PURSE

There’s something undeniably appealing about a proper purse: Smaller than a carryall, bigger than a clutch, prim but not prissy—the right one can elevate just about any outfit. Our favorites at the moment are sleek and structured, done in smooth, supple leathers with simple hardware that adds a touch of polish.

MARNI CARDIGAN, goop, $1,150;
SAVETTE POCHETTE, goop, $1,190

GO FOR A VERSATILE JACKET

A light, easy jacket is a seasonal nonnegotiable. Aesthetically, you have options. A rustic-feeling deep-green topper reminiscent of a traditional waxed-canvas field coat. A cropped, citified camel version with defined seams and patch pockets. Or an elongated leather bomber with cool silver zips. Each one is versatile enough to carry you through the season.