How to Wear Chelsea Boots: Winter 2016 Edition

By Taylor | Trend

Jan 01

Chelsea boots have come a long way since they were first patented by Queen Victoria’s cobbler in 1851. Now, Chelsea boots are a classic staple in both men’s and women’s fashion. According to Tracey Lomrantz Lester of Glamour:

“Classic Chelsea boots are ankle height, have just the teeniest amount of lift (usually a half inch or less), and have elastic panels on the sides so you can slip them on and off in an instant. They also have the unique feature of being all things to women.”

Chelsea boots are classic for a reason–they are both comfortable and versatile. You can just as easily pair them with professional attire as with jeans and a tee, and they transition easily from summer to winter and back again. So this winter we came up with our favorite and most on-trend ways to style your Chelsea boots for the cold weather so you can keep your look fresh in these classic boots.

Want our Curated List of this Season’s Best Chelsea Boots?

With Skinny Jeans and a Chunky Knit

When it comes to an easy and trendy item to pair with your Chelsea boots, skinny jeans are a no-brainer. Stephanie Chon of Bustle says:

[Chelsea boots] go with everything … Oh, and your skinny jeans’ hem will end perfectly right above your bootie.

Skinny jeans are perfect with Chelsea boots because, in most cases, you won’t have to deal with whether or not to tuck your jeans in because most skinny jeans are the perfect length for your booties. For the wintertime, we love pairing skinny jeans and Chelsea boots with a chunky knit to stay cozy but look effortlessly trendy for a casual weekend look.

With Tights, a Skirt, and a Layering Jacket

To dress up your Chelsea boots for some great street style or even a night out, try wearing them with a skirt and tights. Alison Gary of Wardrobe Oxygen says:

Chelsea boots can go glam for a night out on the town. Pair with a little skirt…and black tights for a hip base to show off a fun top.

For winter, we love both midi and mini skirts with tights and Chelsea boots (check out our tips for wearing midi skirts with booties), especially when paired with a statement jacket and great accessories that show your personal style, such as scarves, hats, jewelry, and colorful bags.

With Menswear-Inspired Professional Attire

According to Caitlyn of College Fashion:

“Chelsea boots have been worn in men’s fashion for decades, but haven’t permeated women’s wardrobes until recently.”

This menswear influence means you can, and should, lean into that style, especially when it comes to work wear. We love Chelsea boots with a pair of tapered trousers and a great blazer, or with a balance of masculine and feminine pieces, such as super skinny jeans with a tailored blazer or a boxy sweater.


Want our Curated List of this Season’s Best Chelsea Boots?

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