Scan this QR Code to follow PureWow on Snapchat!
PureWow

We’ll be the first to admit the style can be slightly intimidating. With a fitted, ankle-hugging silhouette and mid-calf height, they’re slightly harder to style than our classic Chelsea boots. But fear no more: With this trusty cheat sheet, you’ll be rocking your sock boots every day of the week.

RELATED: Grandpa Cardigans You Won’t be Able to Take Off This Winter

Boyfriend jeans sock boots

WEAR THEM WITH CROPPED JEANS

Since the boots are fitted at the ankle, they’ll slide right underneath your favorite pair of raw-hem denim, making this look the easiest solution when it comes to your current wardrobe.

Get the Look: Vince Camuto coat ($199); H&M T-shirt ($13); Frame jeans ($245); Naturalizer boot ($104)

Track Pants Sock Boots

AND CROPPED TRACK PANTS

Starting to sense a trend? Cropped styles are the way to go for those just warming up to the sock boot—they eliminate any awkward ankle bunching. Pick a boot with a pointed toe and you’ll also get some amazing leg-lengthening benefits.

Get the Look: Via Spiga coat ($120); Everlane tee ($16); Scotch & Soda pants ($125); Jeffrey Campbell boots ($125)

Orange Culottes Sock Boots

USE THEM TO WINTER-FY YOUR CULOTTES

Hits at a perfect height for you to rock your favorite fall pants well into February. (So long, wool socks.)

Get the Look: Everlane tee ($28); Emerson Thorpe culottes ($285); Sam Edelman booties ($140)

Mini Skirt Sock Boots

AND ELONGATE YOUR LEGS

Because they are tight around the ankle, sock boots won’t cut off a shorter frame like other ankle booties might.

Get the Look: Everlane sweater ($125); A.P.C. skirt ($168); Stuart Weitzman boots ($575)

Pattered Midi Sock Boots

THROW ON WITH A MIDI DRESS

A flowy silhouette contrasts perfectly with a fitted, heeled bootie. Think of this as your office-appropriate go-to.

Get the Look: Billabong dress ($45); Club Monaco coat ($459); H&M boot ($55)

Red Sock Booties Skinny Jeans

SNEAK THEM UNDER SKINNY JEANS

This look could take some trial and error with your current denim rotation, but most pairs of sock boots can fit comfortably underneath your favorite skinnies. Tip: Go with a sleek, stiletto style versus a rounded-toe to streamline your look.

Get the Look: Donna Karan turtleneck ($125); Anine Bing blazer ($349); Topshop jeans ($37); Steve Madden boots ($130)

Wait you need this sock boots

AND DON’T BE AFRAID TO MIX TEXTURES

So you bought a fabulous pair of glittered boots for New Year’s Eve and haven’t worn them since? Pull out those velvet trousers of yours and just go for it. Confidence makes any look a home run.

Get the Look: Jonathan Simkhai sweater ($110); Jenni Kayne pants ($120); Chinese Laundry boots ($90)

PureWow may earn compensation through affiliate links in this story.

From Around The Web