Knee high boots

Boots: Richard Majchrzak/Studio D, Model: Peter Rosa

High Rollers
Q: I love the look of tall boots, but I'm not sure which height to choose. What's the most flattering style?

A: If you're in a skirt, an a-line is best with midcalf and knee-high styles, a pencil skirt is fantastic with knee-high boots, and higher hemlines look good with an over-the-knee or thigh-high version. Since over the knee is already a sexy look, choose a flat or a stacked heel instead of a stiletto to avoid a Julia roberts–in–Pretty Woman flashback. In all cases, to make your legs look longer, wear opaque tights in the same shade as your boots.

From left to right:

Over the Knee
On model: Dress, French Connection, $188; Boots, Stuart Weitzman, $785; Bergdorf Goodman, 212-753-7300.

Via Spiga, $595;

To the Knee

Saint & Libertine, $425;
Transforming boots

Photo: Richard Majchrzak/Studio D

There's nothing I love more than two looks for the price of one, especially when they're as supercute as these: Convertible Ugg Australia boots (left) feature a detachable knit shaft, while Fabulous-Furs' luxurious faux-fur accents (right) take your boots from practical to posh in no time flat.

Convertible Ugg Australia boots: $230;, Duo boots: $315;, Leg warmer: Donna Salyers' Fabulous-Furs, $49;
All-weather boots

Photo: Richard Majchrzak/Studio D

So stylish, you'd never guess they're sensible, too!

Wool Lined
Lacroix, $630;

It's Rubber!

La Canadienne, $395;

Hunter, $325;
Rocker shoes

Photo: Richard Majchrzak/Studio D

These styles are edgy, eye-catching and full of attitude.

Clockwise from top left:
Leopard: $159;, Gray: Report Signature, $130;, Black: $90;, Red: Thakoon Addition, $475;
Menswear inspired heels

Photo: Richard Majchrzak/Studio D

Plaid, houndstooth and oxford details add polish to any outfit.

Clockwise from top left:
Oxford-inspired: Boden, $198;, Red: $795;, Red/Green Plaid: $495;, Black and White: $495;
Minimalist boots

Photo: Richard Majchrzak/Studio D

We've seen the future of boots—and it's sleek and sophisticated.

Clockwise from top left:
Blue: Ostwald Helgason X Aldo Rise, $180;, Indigo: Carlo Pazolini, $275; 646-795-6321, Green: Joseph, $825;, Gray: Vince, $495;
Rugged shoes

Photo: Richard Majchrzak/Studio D

Shearling and suede lace-ups add an outdoorsy-chic vibe to your look.

Clockwise from top left:
Leather: Tommy Hilfiger, $149;, Shearling: $149;, Yellow Nubuck: Mudd, $70;, Green: Joe Fresh, $99; 212-219-2850
Saddle Up

Photo: Richard Majchrzak/Studio D

Saddle Up
Ladies, meet your footwear go-to. Riding boots look great with both pants and skirts, flatter everyone, and are comfy and trend proof. Bonus: There's a best-in-show pair—check out the fresh details on these—at every price point.

From top left to right:



Wanted, $90;
Night boots

Photo: Richard Majchrzak/Studio D

Night Moves
Q: Are boots ever appropriate for dressy occasions?

A: Absolutely! Think of them as an evening shoe: choose heeled ankle booties with special details like sparkles or metallic accents. You can go bare legged, or wear sheer hose or shiny opaque tights for a more festive look; styles that dip slightly in front are extra flattering.

Clockwise from top left:

Shiny Patent Leather
Nina Originals, $198;

Sparkles and a Peep Toe
Via Spiga, $395;

Peekaboo Mesh

Decorative Gold Heel
Raoul, $465;
Moto boots

Photo: Richard Majchrzak/Studio D

Rev up your outfit with these biker-inspired styles.

Clockwise from top left:
Black strapped: Clarks, $150;, Navy: L.A.M.B., $495;, Tan: gx by Gwen Stefani, $70;, Quilted black: $169;
Western boots

Photo: Richard Majchrzak/Studio D

Giddyup to fringe, suede and distinctive stitching.

Clockwise from top left:
Red: $40;, Taupe: $140;, Blue: Miz Mooz, $175;, Tan: $139;
Runway boots

From Runway to O-Way
Fashion-forward, affordable picks that could have just sashayed off the catwalk.

From left to right:

Runway: Chloé
O Way: Kristin Cavallari by Chinese Laundry, $160;

Runway: Alexander McQueen
O Way: Michael Michael Kors, $275; 866-709-KORS

Runway: Versace
O Way: $199;

Runway: Altuzarra
O Way: Isolá, $105;

Boot Rescue

Photo: Richard Majchrzak/Studio D

Quick Fix
This winter, neither rain nor sleet nor snow should keep you from sporting your most fabulous boots. These ingenious wipes—which work on all fabrics, including leather and suede—instantly remove dirt and salt stains, saving your footwear from weather damage.

$7 per pack of 15;