What to Wear: It's Kind-Of Cold Out But Not Really

(Photos: Mario Magnani/Bauer Griffin, Gap)

Okay sure, it depends on where you live—but for wide swathes of the country, October is a less-than-straightforward sartorial month. One minute you get that whiff of fireplace and feel a festive hint of cold in the air, and the next you're leaving your house wrapped up in a cashmere scarf, only to find you need to go back in for sunglasses. As with so many things, the answer lies in a middle path (and channeling Karlie Kloss, pictured above): cropped coats, ankle boots, long-sleeve lightweight shirts and jeans—the ultimate fail-safe plan. Shop our picks below, and get ready to get your autumnal stroll-in-the-park on.

(Cropped Wool Swing Peacoat in Camel and Navy, $148 at Gap)

(From Left: Iona Stripe Slub Tee, $86 at Velvet by Graham and Spencer; Baby Rib Long-Sleeve V-Neck, $24 at American Apparel)

From Left: Jeffrey Campbell Black Washed Leather Hanger Ankle Boots, $165 at SSENSE; O'Neill Taylor Bootie, $76 at Swell)

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