No. 1: Subtle Sexy
You don't have to show a ton of skin to be sexy—these slim-fitting OTK boots showcase your legs, even though they're covered up. Pair this style with a minidress (like the lace H&M style below) to expose just a little bit of leg.
The Lowland Boot, $875,stuartweitzman.com.
Lace Dress, $35, hm.com.
No. 2: Proportion Play
The block heel of this suede style from Topshop gives leg-elongating lift at a heel height comfortable enough to wear all day. The neutral dove gray color works well with pretty much any color you might have in your closet—indigo denim, bright jewel tones, pastels—and is a refreshing break from standard black leather boots. Because the boot isn't tight at the thigh, the proportion works well with a fitted miniskirt and a top with swingy sleeves. Add matte black tights to finish the look—and avoid frostbite.
Suede High Leg Boots, $210, topshop.com.
Wilfred Free Ahrens Skirt, $95, aritzia.com.
Flared Sleeve Blouse, $46, mango.com.
No. 3: Dark Glamour
It's no doubt velvet is the material of the season, seen en force on the runway and entirely perfect for holiday dressing. Velvet over-the-knee boots can be a lot, so it's best to treat these as an outfit accent rather than the star of the show. Go for a peek-a-boo effect by wearing them under a midi wrap dress, which will expose the boots with movement.
Velvet Over The Knee High Heel Boots, $119, zara.com.
Painted Floral Maxi Dress, $188,madewell.com.
No. 4: Everyday Pattern
This floral brocade Sam Edelman boot is the antidote to boring winter footwear. Because this style has so much going on, you'll want to style them with something simple. Your go-to skinny jeans and a simple sweater will nicely balance out any vibrantly printed boot.
Elina Over-The-Knee Boot, $275, samedelman.com.
M.I.H Jeans Paris Mid-Rise Skinny Jeans, $252, matchesfashion.com.
Rag & Bone Jana Two-Tone Merino Wool Sweater, $250, net-a-porter.com.