How to Wear The Chelsea: 10 Outfits with Chelsea Boots

The Chelsea boot has taken the world by storm—lining busied streets with tasteful style and filling the racks of all your favorite boutiques. Adored for its simple and sleek aesthetic, the Chelsea boot stands apart from all other everyday footwear, elevating the most effortless ensembles from modest to modish. Giving you comfortable all-day wear and structured support for your ankles, this understated boot silhouette pairs sweetly with every season’s select wardrobe.

As versatile a shoe as the Chelsea may be, understanding how to wear Chelsea boots may not be as obvious. While the polished architecture of this boot lends itself to pairing well with just about anything in your closet, having a bit of fashion finesse will give you the confidence you need to piece together outfits that look as good as they feel.

In search of some style inspiration? We’ve got you covered. Using this guide, we’ll let you in on all of our best tips and tricks to styling the Chelsea.

The Chelsea: The look and feel

10 ways to wear: Chelsea boot outfit ideas

    The Chelsea: The look and feel
    women wearing the chelsea around the city

    First designed during the Victorian era as a shoe fit for a queen, the Chelsea boot came to life at the request of Queen Victoria. Answering the Queen’s call for a pair of laceless shoes that wouldn’t get caught in her stirrups while horse riding, J. Sparkes-Hall designed the very first Chelsea boot. Distinguished by its ankle-hugging construction and vulcanized rubber inserts, the Chelsea became one of the most well-loved pull-on shoes of the time.

    The modern Chelsea takes the original shape and structure of the Victorian Chelsea boot, but adds a dash of contemporary flair. Rothy’s Chelsea boot reimagines the conventional look and feel of this classic shoe—infusing sustainable materials and low-maintenance wearability into the mix. The Chelsea takes everything you love about Rothy’s flats and transforms it into an ultra-functional pull-on boot with an easy pull-tab for good measure.

    Much like your style, personality and spirit, Rothy’s Chelsea boots exist on a vibrant spectrum of color. From minimalist neutral tones to stylish animal prints, the Chelsea comes in an array of aesthetics that are designed to speak to every woman’s taste. Each pair is crafted from 100% repurposed plastic water bottles and recycled rubbers, meaning they’re as great for the planet as they are for your feet.

    10 ways to wear: Chelsea boot outfit ideas
    woman wearing the chelsea in wildcat posing

    Whether you’re looking for stylish finishing touches for cute winter outfits or a smart shoe that you can wear to work, the Chelsea boot serves as your one-stop-shop answer. Learning how to pair and wear Chelsea boots may seem challenging at first, but once you’ve fine-tuned your eye for piecing outfits together, you’ll open up a world of wardrobe possibilities with your trusty Chelseas.

    Use these 10 chic Chelsea boot outfit ideas to match the essence of the season and vibe of any occasion lined up on your calendar.

    By season

    Despite the fashion industry’s tendency to align boots with fall and winter wardrobes, the Chelsea boot is one of the few exceptions that can stand the test of time and trends—regardless of the season’s changes. Whether you’re preparing for a day spent by the water on a hot summer day or a balmy commute to work in the dead of winter, slipping into your Chelsea boots is always a good idea.


    The Chelsea: Nightfall

    The Outfit: A multi-colored striped turtleneck top with a forest green pinafore dress finished with a pair of deep navy Chelsea boots and sheer black tights is a gorgeous ensemble for any dress up or dress down winter occasion.


    The Chelsea: Fawn

    The Outfit: A white mock-neck sweater tucked into a beige midi skirt looks effortless with a pair of camel brown Chelsea boots. Add some shine to the look with a pair of gold earrings.


    The Chelsea: Wildcat

    The Outfit: A white midi wrap dress paired with leopard print Chelsea boots looks bright, fresh and fun for the season. Tie it all together with a chic crossbody bag.


    The Chelsea: Black

    The Outfit: A cream-colored surplice sweater paired with a black vest and a pair of ankle crop jeans looks as crisp and clean as the autumnal air. Finished with a pair of black Chelsea boots, this cozy ensemble is a fall-time must.

    By occasion

    Your calendar is constantly in motion, demanding more from your wardrobe as the birthdays, brunches and business meetings pile up. Step into each occasion with the self-assuredness and sole support you need with an outfit that is as fashionable as it is functional.


    Working with a dress code can make experimenting with new footwear or clothing feel restricted, but there are a number of unique ways to inject your personal style into your everyday work wardrobe. Simplicity reigns supreme when it comes to styling your Chelsea boots with your office-appropriate ensembles.

    The Chelsea: Black

    The Outfit: A pair of black high-waisted pixie pants with a blush pink scalloped camisole top and a black blazer serves up a professional aesthetic. Tie it all together with a solid black pair of Chelsea boots and a pair of white tortoise shell hoop earrings.

    Date Night

    Maybe it’s your first date, or maybe it’s your fiftieth—no matter how many special nights you’ve spent with your partner, those butterflies fluttering in your chest should be perfectly matched with an outfit that makes you feel as exquisite as the night ahead of you.

    The Chelsea: Wildcat

    The Outfit: A black mini skirt paired with a navy square-neck bodysuit and a matching black vegan leather jacket is elegant, edgy and perfect for a night out on the town. Finish the look with a pair of leopard-print Chelsea boots and a few stacking rings to pull it all together.

    Casual Friday

    Whether it’s dress-down day in the office or just a low-key start to the weekend, there’s no better time for fashion to meet function than on a casual Friday. On your final day before the weekend's welcome, treat your body and your feet to some well-deserved relaxation in an outfit that’s moveable and breathable.

    The Chelsea: Black

    The Outfit: A pair of medium wash skinny jeans, a burgundy scoop-neck bodysuit, a black corduroy trucker jacket and a pair of soft black Chelsea boots serves as the ultimate blend of comfort and low-effort chicness. Accessorize with a silver-accented western belt and a pair of simple stud earrings.


    Seeing the world is no small feat—and it takes a great deal of mileage on your shoes to get you from destination to destination. As you feast your eyes on sights, old and new, the last thing you’ll want to do is slow down. Chelsea boots keep up with your fast pace while protecting your soles and ankles with every step you take.

    The Chelsea: Nightfall

    The Outfit: A pair of comfy black leggings, a plain white slouchy tee and a bright, patterned cardigan paired with a navy blue pair of Chelsea boots will keep you light on your toes, wherever they take you.

    When it comes to footwear that supports your soles, your sustainability goals and your sense of style, settling for anything less than a shoe that speaks to your truth is out of the question. Rothy’s Chelsea boots are the ultimate wardrobe game-changer that brightens your closet with a chic touch.