Photography WIREIMAGE.com (above)

Ankle boots attract cool girls. Think of Chloë Sevigny in high-waisted cut-offs and those low-slung black ankle boots or Kate Moss in skinnies and motorcycle booties, legging it around London. Edgier than a high boot, more fashion-forward than a high heel, this fashion trend has stalked confidently from the fashion runway into fashion mainstream in recent seasons. One rule for wearing them with utmost impact: Make sure that the top of the boot hits you at a flattering point, usually just above or just below the ankle.

Fashion tip: The lace-up

Aldo Sicilian lace-up boot ($150, at aldoshoes.com)

Arguable, winter fashion's most ubiquitous footwear look. A little bit Victorian, a little bit rock-n-roll, all cool-girl chic. This pair adds drama to a long evening coat, or sexy headmistress undertones to a pair of blue jeans.
Inspiration: Rihanna

Fashion tip: Shearling

Material Girl Fulop wedge boot ($100, at thebay.com)

A winter fashion must, as seen on this cute boot, while the wedge heel keeps it grounded in the realities of a Canadian winter. You'll wear it from this season's holiday fetes to next spring's cocktail soirees. Match the laces to the boot for a modern, monochromatic look.
Inspiration: Sienna Miller

Fashion tip: The low heel

Chloé Kenza boot ($835, at davidsfootwear.com)

If Peter Pan had Lost Girls instead of Boys, these are the boots they'd wear to Captain Hook's after-party. Imagine them paired with skinny grey jeans, a classic cotton T and a trilby cocked just so. Never-Never Land won't know what hit it.
Inspiration: Kate Moss

Fashion tip: Play with colour

Topshop Artwork red velvet ankle boot ($136, at topshop.com)

Desert boot meet Doc Martens meet your winter fashion wish list. These come in green as well, but the red is so rich and well, gorgeous. What would you wear them with? Probably everything, but start with ribbed tights, a '90s-style slip dress and this season's oversize chunky cableknit cardis.
Inspiration: Evan Rachel Wood

For more of the best ankle boots for the winter go to the next page...