Cropped Pants + Ankle Boots

ankle boots cropped pants outfit ideas winter street style header

Now that the piles of snow have melted (and left a dirty mess behind), we can all breathe a sigh of relief and finally retire those utalitarian snow boots.

At least until the next snow descends… which might be as soon as later today in Cleveland.

One of the most commonly asked questions I get is about winter footwear. Specifically, “What’s a style of shoe that’s both attractive, yet still practical for those cold days?” Obviously, we’re all familiar with the ankle boot at this point. It’s pretty much a staple. What I think we’re not as comfortable with is actually wearing the ankle boot with anything beyond our favorite skinny jeans or flirty dresses.

Am I right, or am I right? Lucky for you, I’m here to spark your creativity and breathe new life to your winter footwear… or something like that.

A great pair of ankle boots deserves to shine and what better way to show off those fancy feet, than with cropped pants!! Yes, I know… many of you have probably packed away your crops for the season. Do me a favor, though? Go ahead and dig them out.

K, thanks.

While the cropped pants + ankle boots combo is slightly tricker than the skinnies we’re all so used to, the contrast in proportions is fresh and fashion forward and definitely much easier to pull off than you’d think.

Here are 4 different combinations of cropped pants and ankle boots that I fully endorse and stand behind!


Winter White Out

White ankle boots have been having a moment. A simple pair of WHITE ANKLE BOOTS give new life to your favorite jeans — especially when they’re as cool as these RAW HEM CROPS! The overall combination is striking and very “It Girl.”

ankle boots cropped pants street style

Color Coordinated

Remember when I told you about SOCK BOOTIES? Well, in case you were wondering, those are definitely still a thing. If you’re looking for a creative way to get on board with this style trend without taking a plunge, why not try out a pair of matching tights with your favorite pair of ankle boots and CROPPED TROUSERS!? In addition to keeping you just a little bit warmer this winter, the color coordinated style is also elongating and flattering to the ankle and leg.

ankle boots cropped pants raw hem jeans street style

Raw Hem Statement

I adore the look of STRAIGHT LEG RAW HEM DENIM with an ankle boot — in this case a classic pair of CHELSEA BOOTS! The raw hem draws attention to the sharp boots, with the perfect amount of skin exposed in between.

ankle boots cropped pants black street style fashion weel

Classic All-Black-Everything

One thing you can always count on in fashion — black will always be in style. Try your favorite ankle boots with a pair of BLACK CROPPED TROUSERS. It’s probably one of the easiest outfits to put together, yet will instantly make you look chic!

How will YOU be wearing your ankle boots this season?

ankle boots cropped pants

(**A note for my readers: My apologies for the impromptu blog hiatus last week! Moving a family of 4 proved to be a “slightly” bigger task than I ever imagined. Who am I kidding!?? It f^%&#@ sucked! Boxes are getting unpacked, belongings are finally finding their new spaces and we’re beginning to regain some sort of sense of normalcy in these parts. You’ll be seeing more of the finished spaces shortly — a full blog house tour is in the works!)

(Images via 1 // 2 // 3 // 4 // 5)






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