Over-the-knee boots

1. Over-the-knee boot
Adam says the over-the-knee boot is the hottest style of the season. "It's back. Remember we had these in the '80s?" he says. "You want to wear a flat one because if you wear a heel one it's a little too Pretty Woman."

Adam says to match the color of the boot to your tights, leggings or pants. "They can make your legs look longer and leaner if you dress tonally," he says.

Boots: See by Chloé, Zappos.com; coat: Theory, Macy's; leggings: BCBG, Macy's; purse: Chanel, NeimanMarcus.com
Buckle boots

2. Buckle boot
Buckles are a great way to warm up your winter wardrobe. Adam says they're available in every height and style. "You can find these flat, you can find these lower, you can find these as a high boot," he says. "It's a great way to add a little edge to a black pant or simple outfit."

Boots: Botkier in Sander Black, Zappos.com; jacket: Max Azria, Macy's; jeans: Rachel by Rachel Roy, Macy's; scarf: Forenza infinity scarf, TheLimited.com; shirt: INC T-shirt top, Macy's
Slouchy boots

3. Slouchy boot
Channel your inner Pat Benetar with modern, slouchy boots. If you're lean, you can wear them with a skinny jean or a legging. If you're a little curvier, Adam says this boot will look great with a knee-length skirt. "It will camouflage a multitude of things," he says.

Boots: Michael Kors Berkshire Boot in Luggage Suede, Zappos.com; purse: Michael Kors shoulder tote, Macy's; jeans: Seven, Macy's; shirt: Rachel by Rachel Roy, Macy's; scarf: DKNY
Corset boots

4. Corset boot
The peep-toe, lace-up boot is a sexy take on the traditional boot. Adam says women of every age can embrace this trend—wear it with wide-leg pants for an office-appropriate look.

The best part of this style? The lace-up corset makes every foot look narrower. "It makes your foot look longer and thinner," he says.

Boots: Steve Madden Korset, Zappos.com; jacket: Eileen Fisher, Macy's; pants: Nine West wool trouser, Macy's; shirt: Rachel by Rachel Roy, Macy's; purse: Yves Saint-Laurent Roady
Riding boots

5. Riding boot
For a classic look, Adam says a riding boot is a great go-to—especially in gray. "Everyone likes a riding boot," he says. "Gray is very big. It's big in boots and big in clothing."

Have trouble finding boots to fit your calves? Adam has the perfect option for you. "These are extra-wide boots from J.Crew—the best boots out there for a wider calf," he says.

Boots: J. Crew Nottingham boots in gray, JCrew.com; dress: Calvin Klein, Macy's; sweater: International Connection, Macy's; purse: Fendi Peekaboo bag, NeimanMarcus.com

Adam Glassman's Boot Bible:
FROM: Oprah's Shoe, Handbag and Accessory Intervention
Published on November 02, 2009


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