Being a New Yorker who walks a lot, I get the opportunity to often check out what people are wearing.  Everyone is all bundled up in the winter so I can’t see much, but I do get to see what they are wearing on their feet.  This has helped me solve the mystery of what women are wearing with ankle length pants in the winter.  You have to be wondering this too, right?  Ankle length pants made a whole heck of a lot of sense when it was warm but now that the thermometer has dipped and exposed ankles are still a thing.  Well it turns out that the answer is Chelsea boots.  I saw at least half a dozen women wearing them this weekend with their favorite ankle length jeans and pants.

Well now that we’ve solved that problem.

What are Chelsea boots?

Chelsea boots are ankle-high boots that sit close to the ankles that have an elastic  side panels an a back loop to make them easier to get on.  The boots date back to the Victorian era when they were popular for men and women and were also popular during the mod-era of the 60’s.

It makes sense that Chelsea boots would be the go-to choice for women today considering we’re wearing skinny ankle pants and these ankle style boots not only cover the ankles but sitting close enough to the ankles, they don’t cause the hem of the pants to pool up around the boots.  Chelsea boots offer a streamlined silhouette.  Hey, if it was good enough for the Beatles, it’s good enough for us, I say.

Chelsea boots styled five different ways

I created five different looks using these cognac suede Chelsea boots from Steve Madden.  This comfortable boot style can not only work for weekends but in business casual work environments as well.

Outfit #1

chelsea boots

I styled these Chelsea boots casually using a pair of skinny ankle length jeans from Madwell, a shrunken cashmere sweater from Vince in forest green, navy crossbody from Tory Burch, plaid scarf from Barbour and double hoop gold earrings.

Outfit #2

chelsea boots
All black outfits can be nice, but I particularly love the way some outfits looks rich with cognac shoes.  I styled this pair of Chelsea boots with black ankle length pants from Banana Republic, a black tunic from Zara, leopard clutch from Talbots and drop earrings from Halogen.

Outfit #3

chelsea boots
Chelsea boots aren’t just for skinny ankle length pants. You can also wear them with wide and straight leg cropped pants and jeans.  I styled this look with a pair of Rag & Bone cropped wide leg jeans, a relaxed cropped sweater from Topshop, statement pendant necklace and cognac backpack from Rebecca Minkoff.

Outfit #4

chelsea boots
For a business casual look, I styled the Chelsea boots with a pair of plaid ankle length pants, rust colored sweater from Lewit, shoulder bag from Madewell in English saddle and drop earrings from Kendra Scott in sage.

Outfit #5

chelsea boots

This last look I styled with burgundy jeans from DL1961 with an ivory tunic top from Equipment, a blush scarf from Chan Luu and suede crossbody bag in olive from Frances Valentine.

Shop for Chelsea boots

Ready to add a pair of Chelsea boots to your wardrobe?  Check out these additional styles.