Photo: Kana Okada

Clockwise from top-left:

Floral appliqués are cropping up everywhere; these one-and-a-half-inch heels are work-perfect.
Donald J Pliner, $310

Shearling lining for warmth, Nike Air technology for comfort, waterproof suede and patent leather for good looks.
Cole Haan, $248

Take these polished yet casual suede driving moccasins out for a weekend spin.
Tod's, $425

The slightest kitten heel elevates an elegant pointy-toe pump.
Adrienne Vittadini, $99

Studded platform stilettos are a sexy choice for date night.
Colin Stuart for Victoria's Secret Catalogue, $88

What do you wear with red shoes this time of year?
Ideas from O's creative director, Adam Glassman:

• Let them peek out from under jeans, or camel, black, or gray flannel pants.
• Pair dress shoes with brown, gray, or burgundy tights. Avoid black hosiery—the contrast is too harsh.
• Go bare-legged if it isn't freezing outside.

More Great Fashion Finds

• 4 cute and functional winter boots
• 8 match-with-anything pieces under $100
• Put together a work wardrobe on a budget