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

Maxine Eggenberger
·4 min read

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

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

Tory Burch Lila 90mm Zip Up Ankle Boots ($428)

Be Playful With Printed Tights

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

By Far Lange Booties ($578)

Edge Up a Prim Ensemble

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.

Villa Rouge Packer Chelsea Boots ($195)

Search Out Snake Print

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

Bos. & Co. Friend Waterproof Lace-Up Boots ($300)

Make Use of Metallics

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

Anine Bing Charlie Boots ($699)

Update Your Office Wardrobe

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.

Sam Edelman Laguna Boots ($150)

Finish With Faux Fur

Faux fur is as cozy as it is chic.

Loeffler Randall Isla Slim Ankle Booties ($450)

Dress Down Going-Out Frocks

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.

Last Angie Chelsea Boots ($330)

Up the Boho Ante

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.

Loeffler Randall Nellie Block Heel Chelsea Boots ($395)

Try Statement Outerwear

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

H&M Leather Ankle Boots ($80)

Contrast Your Denim

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

H&M Chelsea Boots ($60)

Soften Leather Outerwear With Suede

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

3.1 Phillip Lim Alexa 40mm Boots ($525)

Try Fancy Versions With a Casual Outfit

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.

Ganni Sporty Hiking Boots ($445)

Harness the Power of the Heel

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.

H&M Pointed-Toe Boots ($50)

Don't Pack Away Your White Jeans

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

Jeffrey Campbell Cloudy Waterproof Chelsea Rain Boot ($65)

Keep Things Monochromatic

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

Sam Edelman Dasha Boots ($180)

Add a Shearling Biker

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

Marc Fisher Ltd Paralee Bootie ($194)

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This article originally appeared on Who What Wear

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