From Fall to Winter: How to Wear Cropped Jeans in Winter

A few weeks ago, I asked my Instagram followers about their biggest fashion struggles. An overwhelming number of people mentioned struggling with pairing jeans and shoes, especially in winter. That’s why today, I want to talk about how to wear cropped jeans during winter

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How to Wear Cropped Jeans in Winter

Jean styles seem to be an ongoing struggle for most women my age. Ever since skinny jeans were labeled ‘out of style,’ we millennial women have been trying to navigate new jean styles to figure out what works best for us. Personally, I have adapted to the newer styles, but I still struggle with full-length jeans. I find cropped jeans work best for my body shape.

The problem most women have with cropped jeans is that their ankles get cold in the winter. I get that! Michigan winters aren’t easy to dress for, but I’ve actually found my cropped jeans to be perfect in winter because they stay dry in the wintertime. My struggle with full-length jeans is that I’m short, and they always feel like they’re dragging. I don’t like the back of my jeans getting wet, so cropped jeans have helped me adapt to the wider-leg styles of jeans.

So, how do you wear cropped jeans in winter? The easiest answer is to layer. Just like with any other winter outfit, adding layers to keep your ankles covered is key. I always feel that winter is a season when you might have to sacrifice a little style for comfort. I’d rather wear cute flats and have my ankles exposed, but when it’s cold out, I like to make sure I’m covered up.

Today, I’m going to show you four different ways to transition your cropped jeans from fall to winter.

Related Blog Posts: What Shoes to Wear with Straight-Leg Jeans? and What Shoes to Wear with Cropped Wide-Leg Pants when You’re Petite?

Outfit 1: Straight Leg Jeans + Slim Fit Bootie

I love these cropped straight-leg jeans from LOFT. I think they are the perfect length to pair with ballet flats in the fall. To winterize them, I paired them with booties that have a slim shaft, like these MIA Block Heel booties. When pairing booties with cropped jeans, you want to avoid the jeans bunching up on the boots. That’s why it’s important to find booties that can slide neatly inside the jeans.

Sweater-xsmall || Jeans– 24/petite || Flats– 7.5 || Booties– 7.5 || Coat (similar, similar)

Outfit 2: Black Straight-Leg Cropped Jeans + Chelsea Boots

I love my black Ultra High-Waisted Straight Ankle jeans from Abercrombie. For fall, I typically style these jeans with flats, like my black Mary Jane flats from Walmart, but for winter, I switch to my black Chelsea boots. Chelsea boots are a popular winter style, and I’ve grown to love mine over the past few years because they’re so practical for everyday wear! I like to pair them with boot socks to keep my ankles even warmer. For more Chelsea boot ideas check out my post: How to Style Chelsea Boots with Bottoms.

Sweater-small || Jeans– 25/short || Flats-7.5 || Boots (similar) || Coat– xsmall/petite (similar)

Outfit 3: Wide-Leg Cropped Jeans + Neutral Black Heel Boots

I love my Sailor Wide-Leg Cropped jeans from Target. These jeans originally fit me as full-length pants (see how they look in this post: How to Wear Black Wide-Leg Jeans). I wasn’t wearing them much, so I decided to go ahead and cut them to give them the cropped look they were meant to have. Now, I wear them all the time.

For fall, I’ve been styling these pants with my ballet flats. As the weather cools down, I’ll be switching out my flats for neutral booties. Neutral booties have been a staple in my wardrobe for years, but this pair works especially well with my wide-leg pants. They have a taller shaft that tucks in nicely under my jeans, which helps keep my ankles covered and warm. You could also do a black or brown bootie paired with these pants as well.

Sweater– xsmall || Jeans-0 || Flats– 7.5 || Booties (similar, similar)

Outfit 4: Slim Straight-Leg Cropped Jeans + Socks + Sneakers

These cropped jeans from Abercrombie are the same style as the black pair I shared above. I love this style so much that I’ve bought them for several years in a few different washes. One shoe in my wardrobe that I wear with my cropped jeans year-round is sneakers. They’re so versatile and comfortable—perfect for my everyday mom style.

Personally, I love wearing my sneakers with no-show socks, but when winter comes and I want to keep my ankles warm, I’m all for wearing them with taller crew socks. I know there’s a whole debate about whether you should wear crew socks over 40, but for me, I’ll wear them if it’s practical.

Sweatshirt-xsmall || Jeans-26/short || Shoes– 7.5 || Socks || Coat– xsmall/petite (similar)

Let me know if this post is helpful! Make sure you follow along with me on the LTK app to see how I style my cropped jeans this winter!