Hermes and Devani boots

Best in Show
The suede knee-high with a stacked heel (left) is the Birkin bag of boots: object of desire, trend-defying classic, future icon (Hermès, $2,250). Think ten, 20, even 30 years ahead, and the initial outlay may not seem so outrageous. Coat, Sportmax.

The Height of Fashion: Over-the-knee boots (right) are leading the pack this season (Devani, $165). They camouflage all manner of leg issues (knobby knees, bigger thighs), can be worn full-length or folded down, and look fantastic over leggings or under skirts. Both pairs shown here are in the latest go-with-everything neutrals—beigy grays that you might call (with apologies to the bearded collies) Weimaraner colors. Jacket, 'S by Max Mara. Leggings, Tse.

Get the look: 7 great over-the-knee boots
Michael Kors boots

Stepping Out
The updated scrunch boot (Michael Kors, $895), equipped with an elasticized ruffled top, flatters calves. Crush it down over leggings (Riller & Fount), as shown, or wear pulled up under a knee-length dress. And if you do orange only with black or brown, you're barking up the wrong tree; it's chicer now to juxtapose bold colors—here, a scarlet coat (Moschino Cheap and Chic) and maroon bag (Botkier).
Chloe boots

Old Dogs, New Tricks
The desert boot, a comfort staple since the 1950s, is reinvented as a lace-up heel in its signature sand color (Chloé, $695). The freshest way to wear it is with straight-leg pants (Sportmax) tucked in—the better to see the sharply pointed leather cuff. Wrap, Ralph Lauren Blue Label. Croc tote, Krocoa. On Keazy: Parka, Fab Dog Inc.

Get the look: 18 great ankle boots
Chanel boots

Time for a Walk
A classic square-toe gets an update in fuzzy tweed, and mixed-browns have maximum wardrobe mixability. Keep things playful with patterned tights and a splash of color up top. Coat, Tommy Hilfiger, $380; Tights, Hue, $13, Macy's; 800-622-9748; Boots, Chanel; 800-550-0005 for stores.
Chloe boots

Twinkle Toes
Faux-steel toe-caps and heels with a spray-painted look—graffiti art meets heavy metal—are a witty touch for classic suede knee-highs (Marc Jacobs, $1,000). Pinning on vintage-inspired brooches (R.J. Graziano; House of Lavande) is a brilliant way to punch them up (also a great upgrade for old black boots). Dress, Peter Som. Clutch, VBH. Fishnets, Hue.
Casadei boots - Christian Louboutin booties

A Trend with Teeth
Exposed zippers are everywhere—sometimes functional, sometimes decorative. On this midcalf boot, above left (Casadei, $990), they're both, enabling you to wear the pair half-fastened (the flare makes calves look slimmer) or at their full height. Dress, Michael Kors. Coat, J.Crew. Ring, Mawi.

Beastie Boy: The shoe-bootie with an animal-print cuff, right (Christian Louboutin, $975), is like a perfect pump that grew up and went to Hollywood. Skirt, Erin Fetherston. Rings, Mawi

Get the look: 7 great mid-calf boots and shoe booties we love

Give black boots some pop with brightly colored bags (fuchsia clutch, Krocoa; blue purse, Chanel) or mood-changing patterned tights (pinstripes, Hue; lace, Falke).
Coach boots

Asphalt Jungle
Gray is fall's preeminent shade—an excellent base for stronger colors. Snap on your best friend's leash and head for the street in a double-strapped, stacked-heel boot (Coach, $528). Good news for muscular calves: Your legs needn't be pipestems to fit into this roomy, gaiter-inspired style. Coat, DKNY. Skirt, Diane von Furstenberg. Tights, Fogal.

Get the look: 8 boots made for wide calves
Frye Boots

Rhinestone Cowboy
midcalf boot (The Frye Company, $648) gets a dusting of sparkle.
Donald J Pliner boots

Leather and Lace
Unleash your inner Victorian. Donald J Pliner, $595;
Christian Louboutin boots

Wuthering Heights
Aggressive over-the-knee platforms get toned down with a thigh-length swingy skirt and a medium-sized bag. The loose, slouchy style leaves room to be cre-ative—scrunch them down, fold them over or wear as is; the classic round-toe and heel means they'll be -doing duty as a wardrobe staple long after 2009.

Christian Louboutin; $1,995; Barneys New York; 800-822-7639
Knee high boots

Red Velvet
Stilettos go from night to day when transformed into a covetable knee-high boot.

Charles David; $330;

Get the look: 19 gorgeous knee-high boots

Brass buttons and suede stripes are a welcome addition to a classic shape.

Fendi, $995;

O Boot Guide
O's Complete Boot Guide:
More than 70 styles we love