I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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10 Rules for Effortless, Everyday Style

In this series, I share some simple tips for leveling up your daily looks.

This question has come up a lot over the past year or so as cropped straight leg jeans have become such a popular style of jeans. They’re very easy to wear in warm weather, but what about when the temperature drops? Do you just store them away and wait until the temperature rises?

If you live in a somewhat mild climate, a mid-shaft pointed toe boot is an easy solution that keeps your ankles warm and adds a little edge to your outfit, too. Wear lower socks that are hidden, or for more warmth (and another chance to accessorize) you can have your socks come up higher than the boot.

The exact boots I have on here are by ABLE (and 25% off with Natalie25). I have my true size, but if anything they do run a smidge big so you could consider going down 1/2 size — unless you’ll be wearing really thick socks, of course. I love them paired with these cropped Agolde jeans and that they give me a way to wear the jeans all year round.

I kept the look classic with a black turtleneck (similar and similar) and a trench coat — mine is actually a sweater trench and you can get 15% off with my code Natalie15. This J.Crew long sweater blazer gives a similar look as well. Want a more traditional trench? I love the look of this one. And of course if it’s colder where you live, you can choose an even warmer top layer. Any black crossbody would work with this look, but here’s the exact one I have and also another really beautiful investment option.

Lastly, for a really easy, chic hair option when your hair is dirty, I’m a big fan of the slicked back low bun — I use a french pin to hold the bun in place.

Do you have any boots like this? What shoes do you like to wear with your cropped jeans when the temperatures drop?

P.S. The hammered hoops I’m wearing are a sample from a design I was going to do for the holidays (before I decided not to do a holiday collection). I’ve been wearing them lately and I’m thinking they need to officially be added to a collection this year. Let me know if you’d be interested!

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How to Wear Cropped Jeans When It’s Cold

Read the Comments +

  1. Shelbs says:

    With cropped jeans I prefer white tennis or sandals! Or my slip on vans. I’m 5’2 so the continued look of boot to Jean all the way up -on my body makes me look shorter At least in my eyes, maybe I’m wrong!

    • Natalie says:

      Yes to sneakers and sandals with cropped jeans for sure — especially sneakers when it’s chilly but not “cold.” Classic! Also I’m only 5’4” myself 🙂

  2. Emily says:

    Love the hoops! I’ve been on the hunt for a pair like them. I would love to add them to my NB collection. I live in a colder climate and I recently purchased Madewell’s combat boots to wear with my cropped jeans for extra warmth.

  3. Erika says:

    Love the hoops! Are they lightweight?

  4. Candice Oliver says:

    Ugh…this has been such an uncertainty for me this winter. I live in NY, have so many cropped length jeans, and I’m 5’2”. I have had a hard time feeling like I know what I’m doing trying to pair the cropped length with booties. Often I’m left with cold exposed ankles 😂. At least I’m not out a ton this year due to the pandemic but welcome more tips on pairing similar jeans with a range of booties. As always, thanks for sharing 😘.

  5. Linda says:

    Thanks for the daily it is a great look will do it this week

  6. Laura Gosnell says:

    I love the hoops! I recently purchased a pair of Chelsea Boots from Madewell to wear with my cropped jeans. I am guessing it is a height difference as I am 5’7″ but there is still a small gap between the jeans and boots, so I just wear fun socks.

  7. Love this look, Natalie! I have similar black boots that I wear with my cropped and ankle length jeans when it’s cooler outside. My other go-to footwear for this type of look is a pair of lived-in, white, high top converse.

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Hi, I'm Natalie

I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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