See? These Classic Ankle Boots Literally Go With Everything You Own

They're always the hardest-working item in our wardrobes come autumn, so it's no wonder all we can think about right now is boots. However, with a plethora of new styles out there—think animal print and the square-toe trend favored by celebrities, to name a few—there are almost too many options to choose from. So instead, we're canceling out the noise (just for a second) to focus our energy on a time-honored classic: Chelsea boots.

Chelsea boots have morphed into a perennial fallback. Dating back to the Victorian era when, much like today, they were worn by men and women alike, they traditionally featured flat soles, rounded toes, and sat just above the ankles. In recent years, however, the style has evolved into various iterations, from pointed-toe iterations and tall lengths to chunky tractor treads and wooden heels.

They're so instilled in our lives, in fact, that you probably already own a pair. This is why we're not bombarding you with countless styles to shop for now; instead, we've made it our mission to discover how to wear Chelsea boots now. Be it with jeans, dresses, skirts, or culottes, we're taking cues from these ladies who've helped put Chelsea boots back on the map.

Take the Classic Approach

How to wear Chelsea boots with everything you own: with classic separates

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Outfits don't come more classic than tan outwear, grey cashmere, faded jeans and black Chelsea boots.

Be Playful With Printed Tights

How to wear Chelsea boots with everything you own: printed tights

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Opt for sheer black tights with a subtle print (think pin-point dots or oversized fishnet) to keep the look glossy.

Edge Up a Prim Ensemble

Chelsea boot outfits: edge-up formal attire

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Chelsea boots provide an unexpected sartorial twist to flirty florals, as evidenced here. We also love how they provide a contrast to a formal double-breasted blazer.

Search Out Snake Print

Erin Fitzpatrick fashion editor at Who What Wear attends Copenhagen Fashion Week street style

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Mixing a bold snake print with classic black boots is always a good idea. 

Make Use of Metallics

How to wear Chelsea boots with everything you own: metallic to lift a dark ensemble

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A metallic option will help lift darker outfits, even in the depths of winter.

Update Your Office Wardrobe

How to wear Chelsea boots with everything you own: workwear

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Depending on your workplace, white Chelsea boots can be appropriate attire. After all, there's no denying the cool factor a flat pair with a thick elastic panel can give your trusty trousers-and-blazer combo.

Finish With Faux Fur

How to wear Chelsea boots with everything you own: faux fur

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Faux fur is as cozy as it is chic. 

Dress Down Going-Out Frocks

How to wear Chelsea boots with everything you own: going-out frocks

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Ensure your clothing gets maximum wear by styling it in new ways. These casual Chelsea boots help make this after-dark dress work during daytime.

Up the Boho Ante

Chelsea boot outfits: boho dresses

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Flat Chelsea boots lend themselves so well to boho dresses thanks to their vintage feel. We can see Sienna Miller rocking something not so dissimilar to this in the coming months.

Try Statement Outerwear

Chelsea boot outfits with wide leg trousers

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Let your coat do the talking and pair it with neutral accessories. 

Contrast Your Denim

How to wear Chelsea boots with everything you own: light-wash jeans

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Don't be afraid of pairing a light-wash jean with stompy boots. The outcome is very London.

Soften Leather Outerwear With Suede

Chelsea boot outfits with leather coat

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If your coat and boots both feature a leather finish, it can sometimes look OTT. Instead, pair your cover-up with suede boots.

Try Fancy Versions With a Casual Outfit

How to wear Chelsea boots with everything you own: jacquard

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Leather and suede might be more commonplace, but we're very much here for luxe Chelsea boots, too. Take this jacquard pair, for example—they help elevate this tonal ensemble with their eye-catching shimmer.

Harness the Power of the Heel

How to wear Chelsea boots with everything you own: petite styling

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If you're petite, look for Chelsea boots with not only a heel but also a stacked sole, as they'll give you added height and will help keep your frame in proportion.

Don't Pack Away Your White Jeans

How to wear Chelsea boots with everything you own: white jeans

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No longer reserved for summer, white jeans can look the autumnal part with the help of burgundy boots. 

Keep Things Monochromatic

How to wear Chelsea boots with everything you own: monochromatic

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Can you imagine a cooler outfit than a grey checked blazer, a black printed skirt and monochromatic Chelsea boots? Nope.

Add a Shearling Biker

How to wear Chelsea boots with everything you own: biker jacket

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Style du Monde

Nail the off-duty model look with a biker jacket, slim-fit jeans and a sweatshirt.

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