Flat Ankle Boot—Make practical flat boots tough-girl chic with lots of layers and a pop of unexpected color.
Above, from left: Topshop Faux Fur Hat, available at Topshop; AE Skinny Jean, $49.50, available at American Eagle; Armani Jeans Faux Shearling Jacket, $521.36, available at Jules; J.Crew Jackie Cardigan, $39.50, available at J.Crew; J.Crew Cashmere Scarf, $69.50, available at J.Crew; Forentini and Baker Boot, $585, available at GravityPope.
Hardware Boots—Pair a hardware-heavy boot with feminine pieces to keep the look fresh and youthful.
Above, from left: Matthew Williamson Batik-Print Wool Scarf, $495, available at Net-A-Porter; Gucci D-frame Acetate Sunglasses, $138, available at The Outnet; ASOS Patchwork Faux Fur Coat, $129.30, available at ASOS; Marc by Marc Jacobs 5 Buckle Ankle Boot, $215, available at Barneys.
Over-The-Knee Boots—Keep over-the-knee boots classy and fun with a full-skirt in an interesting print.
Above, from left: MaxStudio Miro Boot, $229.95, available at Nordstrom; BCBG Cat-Eye Sunglasses, $80, available at BCBG; Marc by Marc Jacobs Quilted Purse, $360, available at Net-A-Porter; Levi's Roots Leather Biker Jacket, $413.76, avaiilable at ASOS; Dangoon Cable Knit Scarf, $25, available at YesStyle; Nastygal Navajo Blanket Skirt, $45, available at Nasty Gal.
Above, from left: Tolani Leopard Scarf, $99, available at Singer22; Betsey Johnson Military Ponte Wool Long Coat, $495, available at Betsey Johnson; Kelsi Dagger Ankle Boots, $99, available at Endless; AE Ripped Denim Cut-Offs, $36.50, available at American Eagle Outfitters.
Riding Boots—Play up your feminine side by pairing flat equestrian-inspired boots with a flirty dress and an empire-waist coat.
Above, from left: Aigle Ecuyer Boots, $189, available at J. Crew; Miu Miu Funnel-Neck Wool Coat, $1148, available at Net-A-Porter; Grandoe Red Leather Gloves, $60, available at Last Call; ModCloth Trollied Dolly Paint Me a Picture Dress, $74.99, available at ModCloth.
Above, from left: Vince Ankle Corduory Pants, $220, available at Saks Fifth Avenue; VKoo Fingerless Gloves, $125, available at Diana Boutique; Topshop Wool Buckle Cape with Fleece Collar, $160, available at Topshop; Alexander Wang Rocco Mini Duffle Bag, $1,156.27, available at MyTheresa; Tory Burch Halma Suede Bootie, $315, available at Tory Burch.
Knee-High Boots—Wear classic knee-high boots with high-waisted pants and your legs will look like they're a mile long.
Above, from left: Levi's High Rise Denim Stirrup Legging, $68, available at Urban Outfitters; AE Plaid Shirt, $34.95, available at American Eagle Outfitters; Wanted Shoes Knee-High Western-Style Boots, $79.99, available at Endless; BCBG Studded Belt, $28.80, available at BCBG.
Feeling crafty? Check out these DIY boots with fur to keep you warm all winter long...
Photos by Mr. Newton