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How to wear cropped jeans in autumn and winter? Trendy outfits and combinations

Whether dressed up or down, cropped jeans remain a timeless classic for all seasons. When the weather outside is frightful, your first instinct might be to reach for long pants. But what if we told you that you can still wear your favorite cropped jeans in the winter? It’s true! Fall/winter fashion trends offer plenty of inspiration to elevate traditional denim looks this season. With a few styling tips and the right combination, you can wear “cropped” jeans all season long, and it’s not only fashionable, but practical as well. So, how to style cropped pants in winter?

What actually are cropped jeans?

Cropped jeans to wear in fall and winter with leather jacket

Cropped jeans are a fashionable and comfortable way to show off your legs, and they can be paired with a variety of accessories. The word “cropped” comes from English and means something like “cut off”. The best cropped jeans end just above the ankle. It’s a proportion that’s perfect for petite women, but equally stylish at all heights. Wearing cropped jeans in the fall and winter is perfectly acceptable. In fact, many people believe cropped jeans are better than full length jeans when worn with ankle boots. Just pair your cropped jeans with the right top and a jacket to keep warm.

Cropped jeans outfit combinations for the colder months

There is a wide range of cropped jeans: skinny-leg, straight-fit or bootcut in different fit options – some are made of stretch denim, others have a loose shape and denote the “boyfriend” style.

You’ve seen them everywhere, but how do you actually wear them without looking ridiculous?

Length is the key to making this look flattering! Find jeans that end just above your ankle.

Choose the right shoes

Cropped jeans with booties for a chic look

If you’re looking for a pair of shoes that will go well with your cropped jeans, you’ve come to the right place!

We know it can be difficult to find clothes that match your style, but it’s not impossible at all. And we want to make sure you have all the information you need to put together the perfect outfit.

That’s why we’ve put together our top three shoe combinations to go with cropped jeans. Each of these styles is perfect for any occasion and will fit seamlessly into any wardrobe, so you can feel confident no matter what you’re up to.

  • Many women’s favorite shoes for the fall days are the ballerinas and the loafers. They just go very well with cropped jeans. The only downside is that part of your leg is exposed.
  • Sneakers or high-top sneakers also go great with these jeans. They are more casual than booties and more comfortable.

Sneakers and blazer for everyday wear

  • When considering how to wear cropped jeans in the winter, ankle boots are the most obvious choice as they are cool weather footwear. Essentially, cropped jeans should almost reach ankle boots or you can combine them with sock boots that fit under the shortened jeans. Chelsea boots are hot right now and pairing them with cropped jeans is a great option.

Tops to wear with cropped jeans in fall and winter

Cropped jeans with floral print blouse for a trendy look


When it comes to making cropped jeans look flattering, you should create the shape. Here are some tips for tops that can be worn with them.

  • Do you want a trendy look? A floral print top will dress up your casual look. Tuck the shirt into your pants for a dressy look and slip on a pair of ankle boots for some height.
  • Choose a tight-fitting top and layer a long cardigan over it. Some tips: Wear heeled shoes or booties to create long lines and tuck in your top to accentuate your waist. Be sure to skip the super wide leg jeans if you opt for a longer cardigan so you’re not swimming in fabric.
  • Wear a sweater and make a front pleat to keep a visible waist.
  • Throw a teddy jacket over your white top for an extra layer of warmth. Tuck or knot your tee to show off your waist and create a flattering look, especially with jeans that have a higher waistline. Pair with your favorite sneakers and you’re good to go!
  • If you’re looking for an outfit for a date or the office, try this combination! Blazers are trending right now and look great when paired with cropped jeans. Wear black under the blazer for a sleek or professional look when you go to the office.
  • Choose an oversized jacket and pair it with Chelsea boots. Try to accentuate the waist with a t-shirt or cropped top tucked into the pants.

Cropped jeans with boots and coat for winter outfit

When in doubt, go dark! When trying out a new trend, sticking to subtle hues is your best friend. Throw on a pair of white booties if you’re feeling funky, or black if you want a monochromatic look (with a black bag to complete the look).