How This Michigan Girl Wears Cropped Jeans In Winter

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Typically, once winter rolls around here in Michigan, I retire my cropped denim. Michigan winters are cold, and winters in Michigan’s Upper Peninsula? Even colder. This is no place for bare ankles. That said, while I’ll be happily wearing skinny jeans much of the winter, I am hoping to get more use out of my cropped jeans. My secret?

Get the BOOTS + JEANS pairing exactly right.

How To Wear Cropped Jeans In Winter

I’m happy to report that these Sorel wedge boots — my longtime favorites — are one pair that works beautifully with these cropped step-hem MOTHER jeans. Taking the time to figure out a winning combo has saved me so much time getting ready in the morning.

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

jeans | sweater | coat | hat | mittens | boots

Once I realized that these step-hem MOTHER jeans could work with my Sorels, I knew they were worth creating a daily uniform around.

1. Start With A Black Cashmere Turtleneck

Enter: black cashmere turtleneck, sweater I reach for allll the time. When I’m cold? Black cashmere turtleneck. When I must look presentable for Zoom but am in sweatpants? Black cashmere turtleneck. Dressing down a skirt? Black cashmere turtleneck. Dressing up jeans while keeping things comfy? You guessed it: black cashmere turtleneck.

A black cashmere turtleneck is simply one of those pieces that works with everything. And this one, specifically, has become a TME team favorite for a reason: soft, drapey, and perfectly cut (we recommend sizing up one size), and is shockingly affordable.

So a black cashmere turtleneck + the cropped step-hem MOTHER jeans has become my daily uniform. The jeans are the perfect length to show off boots without freezing your legs and, true to MOTHER denim, they have an incredible fit with just enough stretch to be comfy without losing their shape.

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

jeans | boots

Outfit Option A: Add A Bright Coat, Sorel Boots & Warm Winter Accessories

So take your comfy black cashmere turtleneck, cropped jeans and warm boots outside with a long coat, cozy hat and mittens. I love the bright color of this coat–it pretty much goes with all of the typical blacks and greys in my closet, and adds a fun pop of color. There’s just something about a red coat in winter, right? This one zips all the way down but has buttons on the side for easier movement (like getting in and out of the car). I love the stand-up collar and hood, too.

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

Sh*t That I Knit

OK, we have to talk about these winter accessories. Aside from the fact that they’re high-quality and super-warm, they’re also handmade by a team of women in Lima, Peru from sustainably sourced materials. The women knit from home so they’re able to care for their kids while earning a fair wage to support their families. So you can feel good about wearing these adorable hats with interchangeable pompoms (love that feature). Oh and Sh*t That I Knit also donates Knit Kits that teach young adults undergoing cancer treatment how to knit–another reason to love them.

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

Outfit Details

jeans: MOTHER Insider High Waist Crop Step Fray Jeans (28, tts, wearing sweet and sassy color)–MOTHER denim is SO good, especially for curves. I loved the shorter length of these (I’m 5’4″), but if you need a longer inseam these are similar but just about 2″ longer–or you could always add some comfy boot socks!

sweater: Halogen Cashmere Turtleneck Sweater (s)–Love this cashmere sweater. Shana, Gwen and I all own it and love it. (And it comes in lots of colors to choose from!)

coat: VERO MODA Upsala Hooded Quilted Coat (s)–This coat is really lightweight, and I love the bright color and length. I also like that it zips the entire length of the coat, and there are buttons on the side for easier movement.

hat: Sh*t That I Knit The Rutherford Merino Wool Beanie with Removable Faux Fur Pompom–really warm, and I love the fact that you can switch up the pompoms or just go without.

mittens: Sh*t That I Knit The Motley Merino Wool Mittens–love the texting hole for fingers!

boots: SOREL Joan of Arctic II Waterproof Wedge Boot–incredibly warm and comfy, there’s also a shearling version!

Outfit Option B: Try a Long Cardigan & Booties

I love the longer cardigan over the turtleneck, especially with the cropped length of the jeans that show off the booties. (These jeans work with everything from those Sorel wedges to ankle booties and even pumps or sandals, so they’re perfect for multiple looks.) The cardigan is made from a recycled polyester blend that’s warm and cozy, not itchy. It’s stretchy too, which makes it easy to layer over sweaters–I hate when sweaters don’t have enough give to them, and they feel too constricting when you layer them. This one is really comfortable. (Also in grey or green.)

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

jeans | sweater | cardigan | booties

A note on socks: If you are taller (and your socks tend to show between the boot and the jean), the rule of thumb is to (roughly) match the socks to either the jean or the boot. My socks don’t really show, so black socks + dark jeans are good enough. However, these UGG boot socks would also work with these camel boots (and they’re nice and long for warmth).

How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.
How to wear cropped jeans in winter? It's all about the boots or booties. Throw on a black cashmere turtleneck; layer it up; problem solved. Outfits styled, inside.

Outfit Details

jeans: MOTHER Insider High Waist Crop Step Fray Jeans (28, tts)–MOTHER denim is SO good, especially for curves. I love the shorter length of these (I’m 5’4″), but if you need a longer inseam these are similar but just about 2″ longer.

sweater: Halogen Cashmere Turtleneck Sweater (s)–Love this cashmere sweater. Shana, Gwen and I all own it and love it. (And it comes in lots of colors to choose from!)

cardigan: VERO MODA Gaiva Long Open Cardigan (xs)–This cardigan is super-versatile–wear it with jeans or leggings, or layer it over a dress for a cute date night look. Also in a really pretty green or gray, I love the length and coziness of this cardigan. (And those cuffs!)

boots: CC Corso Como Ellie Bootie–LOVE the color of these boots (it looks a bit different in the product image). The heel is a walkable 2 1/2 inches, and the shaft is soft and comes up high enough to keep your ankles warm! (Also in black or dark brown suede.)

XOXO,

Scotti

A huge thank you to Nordstrom & ShopStyle for sponsoring this post. Nordstrom has always been my go-to place for comfy, fancy, and everything in-between, and their free shipping/free returns, clean website, and huge inventory make it an easy first choice. Signing up for the Nordy Club also gets you benefits like Nordstrom Notes (money to spend on Nordstrom purchases), alterations credits, curbside pickup (if you’re lucky enough to live near one), and early access to the Anniversary Sale, to name a few.

Photo Credit: Abby Paquet And Abby it was so fun to meet you and work with you!

And as always, a HUGE thank you to our readers for your continued support–it is so very much appreciated!

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9 COMMENTS

  1. Completely agree with the black turtleneck. And as a knitter I’m going to try to make those mittens! But I couldn’t figure out why socks weren’t in the discussion. I need Can here, please…. Cam and us taller people have a good 4 inches between the boot and the crop. I’ve been trying some awkward sock combos, close but no cigar.

  2. Yeah! Fellow Michigan resident here. I want you guys to know that I finally broke down and bought that turtleneck after reading like, I don’t know, 300,000 posts about it. The verdict? AMAZING. I haven’t taken it off. I might order more I love it so much. Thanks!

  3. This is really helpful. I’ve been really confused by sooo many jeans styles lately and what shoes to wear with them, especially in cold weather!

  4. Does anyone know if the Sh*t That I Knit removeable pompoms would work with satin-lined beanies? #curlyhairprobs If so, I know what’s going in my stocking! 😉 Fingers crossed!!

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