Despite the ever-shifting footwear fads, knowing how to wear Chelsea boots is a hallmark of a true fashion pro. They're a classic for a reason, after all. The real ones know that the best Chelsea boots are understated, elegant, and edgy all at once.
For those unfamiliar, the unisex style is typically defined by its elastic side panels, which allow it to seamlessly slip on and off. Other than that, the footwear is entirely customizable. The wardrobe staple can range from contemporary chunky soles à la Dr. Martens to Prada’s sleek black leather signatures.
Our Favorite Chelsea Boots for Styling
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Named for the Chelsea neighborhood in London, and first designed as a riding boot for Queen Victoria, nearly two centuries after it was first designed the slip-on style is still going strong. The perfect footwear for colder months, Chelsea boots are comfortable and practical. Because of this, they’re often relegated to casual weekend outfits. The looks we’ve shared below, however, prove the shoe works just as well at the office as it does at your dressiest party.
You don’t have to stick to basic black, either. Brown Chelsea boots are currently everywhere. And while leather boots are always a welcome addition to any capsule wardrobe, suede is also trending (especially for men’s Chelsea boots). So whether you’re looking to invest in new Chelsea boots or simply want to refresh your favorite pair, we predict you’ll be wearing the footwear on constant rotation this winter. Keep reading for outfit ideas on how to wear Chelsea boots with all the latest trends.
The rock-star-approved way to wear Chelsea boots is with black jeans. But this street-style look above proves how well they work styled with color. If you prefer your outfits to be more vibrant and favor dresses and skirts over trousers, a pair of sleek black ankle boots are the answer. They anchor almost any look.
With boho chic making its grand return to the runways, the art of pairing a flowing maxidress and a chunky shoe is back in full force. Though Chelsea boots can lean more utilitarian, they’re also versatile enough to couple up with brightly patterned midi or minidresses. For some sartorial bonus points, experiment with colorful boots in a shade that matches or complements your dress. Adding a leather jacket or vest on top is a nice way to balance the chillier weather too.
This outfit idea teams tailored pants with leather Chelsea boots and a fuzzy vest. In the colder months, we’d also layer this street-style look with a turtleneck underneath to avoid the chill. Less is more with this ensemble—a pair of simple silver hoop earrings, a classic watch, and a minimalist bag are the only accessories you really need.
Really good blazers and jackets are one of the best things to come from the “office siren” trend. An oversized blazer—whether it’s accompanying equally baggy black jeans or disguising a miniskirt—adds a structured workwear touch to the slip-on boots. Upgrade the combo by accessorizing with some eye-catching socks or statement tights. Alternatively, the utilitarian feel of an oversized military-style coat is a good balance to the durable boots. The twist comes from a dainty slip dress or skirt worn beneath.
Wearing Chelsea boots with a full suit is a workwear power move. Dress shoes like stilettos can only get you so far (literally), and the sleek, pointy-toe boots fit right in with tailored trousers and a fitted jacket. It’s an office-friendly style that has that formal look without sacrificing comfort for your nine-to-five.
Comfortable, warm, and ever so stylish, Chelsea boots with straight-leg jeans is forever a classic look. Keep it elevated, luxurious, and on trend by adding a suede coat. Sophisticated touches like a mini handbag, elegant gold earrings, and a slicked-back pony will keep the look polished even if you decide to swap the denim for joggers or leggings. Either way, it looks great for a weekend brunch date.
To be fair, jeans go with everything—but a Chelsea boots and denim combo always delivers. The denim silhouette is truly up to the wearer with these shoes: Throw on a pair of slouchy, wide-leg jeans to show off just the top of the boots, or make your shoes the star of the show by styling them with a slim-fit look or cropped jeans. However, as the denim pendulum starts to swing back toward skinny cuts, you’d be on trend to channel Harry Styles circa 2015. He rocked a pair of Chelsea boots and skinny jeans like no one else.
Rain or shine, Chelsea boots and trench coats are a match made in fashion heaven. A statement trench—whether buttoned to the top, belted at the waist, or casually showing off the full ’fit—pairs well with the slip-on footwear. It works with any timeless beige trench and brown suede boots, or even a head-to-toe leather look complete with a longline black leather trench and platform Chelsea boots.
Here’s a master class in styling black Chelsea boots—and proof that brown-and-black outfits totally work. The combo of a brown leather jacket with slim dark-wash jeans and black shoes is effortless but sophisticated. Another styling tip: Opt for a button-down shirt instead of a T-shirt to dress up your ankle boots a little more. If you prefer a looser silhouette, wide-leg jeans or a barrel cut are another great option here.
Wondering how to avoid sliding across the sidewalk or catching a cold and still stay fashionable in extreme weather conditions? Invest in a pair of slip-on, water-resistant Chelsea boots now. Extra points if they have a lug sole to give you a little bit of extra height. Keep your hair protected from the elements with a trendy and warm hat, while a belted coat will give the outfit form and shape.
Your favorite dresses and skirts don’t have to collect dust in the back of your closet during sweater weather. Transition them to match winter boots by experimenting with textures and patterns, like mixing a tiered maxiskirt with a suede Chelsea boot or contrasting a flowy lace maxi with a button-down shirt and chunky leather.
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Your instinct might be to style Chelsea boots with pants, but they’re a nice balance for shorter hemlines too. Balance the neutral tone of the shoes with a simple T-shirt, cardigan, or button-down top, then feel free to go wild with a patterned skirt in between that matches your personal style. You can wear this formula in the spring or winter—all you need to do is wear a long-sleeve top and add tights for cold weather.
Why not style Chelsea boots with an evening dress? On the days when you need an extra-special outfit that won’t leave you freezing in the winter weather, a long chiffon dress, an elegant coat, and sturdy flat black boots is chic, refined, and surprisingly practical. Throw on a pair of thick-rimmed sunglasses for added confidence and attitude.
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