I did that thing I do. That thing where I lock myself in my room for several hours and only emerge — sweaty, hair messy, squinting — after the entire contents of my closet have been relocated to my floor.

It’s my…”specialty”.

Mike loves it. (HA)

In this case, I was systematically trying on every possible combination of jeans & boots, in an attempt to shed some light on Which Boots Could Possibly Be Worn With Cropped Jeans In The Winter.

There were several failed attempts.

How To Wear Cropped Jeans With Boots In Winter

I then changed tactics and tried to come up with At Least One Boot, Dammit, That Can Be Worn With All Of My Cropped Jeans Or Maybe Even 2/3 Of Them Yes I Will Take 2/3 Success and that, my friends, worked.

Part of the problem, I think, is that not all cropped jeans are created equal. Cropped skinny jeans are easy. (I took on that one a couple of years ago — see here.) It’s the rest of them: mom jeans, boyfriend jeans, cropped straight leg jeans, cropped wide-leg jea– crap.

I forgot about cropped wide-leg jeans.

[S bangs head on desk]

BUT WHATEVER. I’m hours & hours into this article, so we are going to FINISH it. And if we’re all still confused when I am done…I will mess around with cropped wide-leg jeans later. In a different article. In 2034.

So. The problem, I found, is that mom jeans and boyfriend jeans and straight leg jeans are often cropped to different places on the leg, and sometimes the legs are rolled up, sometimes the legs are rolled down and while in general I like to have a rule about this sort of thing it is not an exact science aka I give up.

Instead, I grabbed four of my most-worn pairs of cropped jeans (we can debate whether they are of the mom, straight or boyfriend jean variety at a later date), and I tried to find boots that worked with all of them.

And?

I found three styles of boots that are as close to foolproof as we’re going to get.

First Up: The Cropped (Not Skinny) Jeans I Wear The Most

I shot these barefoot, and rolled down the cuffs (on one of them), just so you can get an idea of length (I’m 5’3″ for reference).

The 1 where we systematically try every combo of jeans & boots, in an attempt to shed  light on Which Boots Can Possibly Be Worn W/ Cropped Jeans In Winter.

featured sweater: Halogen 100% cashmere turtleneck

TOP LEFT: Levi’s 724 Straight Crop (size 26) – SUSTAINABLE – these were the super-soft Levis I wore alllll summer and they’re still going strong. You can see more photos (and detail shots) here.

TOP RIGHT: Citizens of Humanity Harlow Ankle Slim Jeans (size 26) – SUSTAINABLE – I was really excited about these jeans — they’re insanely comfortable to wear — but…something is off? I think I need to crop them a bit.

BOTTOM LEFT: MOTHER Tomcat Jeans (size 25) – the exact wash I’m wearing is this one, but sizes are limited. I actually like this slightly distressed wash better (also at Nordstrom). I never actually wear them unrolled like this, but wanted to show the length (I’m 5’3″).

BOTTOM RIGHT: Everlane’s ’90s Cheeky Straight Leg Jean (size 26 ankle) – this is another pair of jeans that I’ve been thinking about cropping further…maybe just one more inch? (And Everlane just came out with a really pretty light blue wash if you are obsessing over light washes as much as I am right now.)

The 3 Best (Most Foolproof) Boots to Wear With Cropped Jeans

1. Western Booties

One of the best parts about western booties is that they aren’t necessarily brand-specific; almost any type of western bootie will work with cropped jeans! That’s thanks to the shape, I think, specifically the higher, narrow shaft, the slim ankle and slight heel.

featured: PAIGE Willa Bootie (size up a 1/2)

The 1 where we systematically try every combo of jeans & boots, in an attempt to shed  light on Which Boots Can Possibly Be Worn W/ Cropped Jeans In Winter.

Top 3 Favorite Western Booties

  1. PAIGE Willa Bootie (size up a 1/2 size)
  2. Everlane Western Boot (see Julieta rocking them 9 different ways here)
  3. Splendid Cherie Ankle Boot (Emily turned me onto these, love the higher shaft — see them on her here)

2. Combat Boots (Especially Doc Martens)

Combat boots are another great choice for pairing with cropped jeans — especially in the cold. Like the western bootie, they have a higher shaft, and are slim along the ankle (thanks to the lacing), with a slight lift in the heel.

One note: Of all of the combat boots, Doc Martens seem to work the best. Other combat boots *do* work, but if you need a pair that really comes up high on the leg and is slim enough to tuck under jeans, Docs are a safe bet.

featured: Doc Marten Leona boots (more sizes here)

The 1 where we systematically try every combo of jeans & boots, in an attempt to shed  light on Which Boots Can Possibly Be Worn W/ Cropped Jeans In Winter.

Favorite Combat Boots

3. Sock Boots

High-heeled booties, in general, are an easy win with cropped jeans. And sock booties, specifically, are simply high-heeled booties with a longer, narrow shaft that slips nicely underneath jeans.

Even better, there are two different sock booties that really stood out as being virtually foolproof to style with cropped jeans.

3A. Everlane The Glove Boot, ReKnit

OK, so not only are these boots made from recycled polyester (yay!!), but they were literally created for exactly this situation. The knit upper (which can be spot-cleaned with soap & water) was designed to fit all ankles, so they look good with bare legs, or slipping under jeans. I also love the walkable heel. It’s just high enough to feel like a high heel…but not so high you can’t walk in it.

featured: Everlane’s ReKnit Glove Boots

The 1 where we systematically try every combo of jeans & boots, in an attempt to shed  light on Which Boots Can Possibly Be Worn W/ Cropped Jeans In Winter.

3B. Jeffrey Campbell Siren Bootie

If you want an unapologetically sexy black bootie…Jeffrey Campbell’s Siren Bootie is my fav. It’s made from a neoprene fabric so it slides right under jeans, and it’s nice and tight on the ankle. Because of the neoprene it does stretch a little, but not nearly as much as the Everlane knit boot.

This boot is comfortable for an entire date night…but not for walking very far. Short distances are all I’ll do…and even then, if it’s more than a block or so I’m happier in the Everlane boots.

featured: Jeffrey Campbell’s Siren Bootie

The 1 where we systematically try every combo of jeans & boots, in an attempt to shed  light on Which Boots Can Possibly Be Worn W/ Cropped Jeans In Winter.

Sock Booties That Work With All the Jeans

So that’s it! These are the three boot types that are the most foolproof way to style cropped jeans in winter. It has been easier getting dressed lately, knowing exactly which boots go with which pair of jeans.

Ah, clarity.

I’m curious though — how are you guys styling your cropped jeans in winter? (Or have they just been lying in a pile in your bedroom?) Feels good to branch out.

xo,

S

10 COMMENTS

  1. Thanks Shana! I’ve been wearing mine w high top leather converse. Kind of the same look as the docs – sneaker version(?). Really tempted to join the doc bandwagon.

  2. I LOVE this. Thank you. I am a sock boot convert. I found a great pair at Anthropologie and now I am hooked. Please keep doing this- I need help knowing what shoes go with what jeans (skinnies, straight leg, flares, mom jeans etc.) I tend to like things with a bit of a heel. And also, PLEASE tell us where you got the jacket at the top of the post. I think I need it.

  3. I love my Everlane knit booties – I have them in two colors and wear with all my cropped jeans. I also wear sneakers with my cropped jeans.

  4. I love this article! That sweater is one of my most worn pieces and I’m loving all of these boots with the different jean styles, most especially the Dr. Martens. Which I’ve always loved and worn, but I just read a light essay on Gen X, so I’m feeling extra fond of my badass footwear choice! 😂 Sock boots are definitely next on my list of purchases, though!

  5. I cheat and live in California where showing some bare skin is fine year-round 😛 That said, I haven’t found my perfect sneakers yet (my feet are super picky about what they can handle without socks), so I do wear my cropped jeans with booties most of the time. The key is just to get the top of the boot fitted to your calf — I have a pair of basic black Chelsea boots from Thursday Boot Co, for example, which work well because they have a very fitted shaft opening. An intentionally flared shaft opening can work too, but it’s less streamlining.

  6. So I’ve been cheating and wearing regular old booties with boot toppers (which I wear upside down and inside out to fit with the larger part covering the top of the boot since they won’t stay tucked into booties) I get so many compliments every time. And the knit top makes the boot look go inside the cropped leg 😃

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