Boot Camp: A Style Guide

Get a leg up on the boot-sock trend

Welcome to Boot Socks 101, where you’ll learn how to master this season’s best boot-styling trends. The onset of winter brings a need for more layers, and this year is especially layering-friendly with the explosion of boot accessories. Here’s what’s out there and how to wear each look:

Boot socks come in a variety of styles and lengths. A popular look is the mid-calf length with the top of the sock slightly scrunched. This is best achieved with a thicker material. Madewell offers an ideal slouchy sock. Thinner pairs are best to wear over tights so they don’t feel too bulky. Follow the general rule of wearing shorter socks with shorter boots and taller socks with taller boots. However, if you would like to mix it up, tall, thin socks look cute with short, clunky boots. Urban Outfitters has a Pointelle pair that would work well for this look. Also, Nordstrom has ruffled ankle socks that would be adorable with booties.

Boot cuffs or boot toppers are great with boots that already keep your feet warm enough. Boot cuffs are just a band of material, meant to mimic the top of socks. They should be positioned around the leg where the top of your boot hits so they peek out. Best in a thick knit to prevent slippage, cuffs often showcase a different style on each end, making them reversible and versatile. Etsy is a great source of cuffs, like this cable-knit brown-and-cream-colored pair.

Boot liners are meant to be worn with rain boots. Usually made of fleece, they act like socks and fold over the tops of boots. Many top brands like Hunter and Betsey Johnson make liners specifically tailored to fit their boots. Macy’s carries ’em in various colors.

Legwarmers are back from the ‘80s, but sans the bright blue and pink. Common in thick knits, the new version is usually worn inside the boot, allowed to stick out the top like boot socks. They can also be worn over high-heeled boots, pulled down to cover at least half of the heel. Pick a pair with cute details to allow for a more modern touch. Anthropologie offers a tan pair with small, furry pom-poms attached (pictured).

Tights are still a must, patterned or solid. The current must-wear trend is to pair tights with boot socks or legwarmers and boots. This allows you to take that summer dress into the colder seasons. Free People has a good selection of black patterned tights, including the adorable “Queen of Hearts” style.

Want more? The Cut blog by New York magazine paired 50 boots with 50 socks.