Want to Wear Cropped Pants in the Colder Seasons? Here’s What to Know

Want to Wear Cropped Pants in the Colder Seasons? Here’s What to Know

Cropped pants are one of our warmer weather staples. Airy, comfortable, sophisticated, yet down to earth, women’s cropped pants are truly a gem. Practical and stylish, there’s always that time when we lament having to tuck them away until next year. Cropped pants are great for warm temps, but as soon as the weather turns cold, frigid ankles are enough to convince you to venture back to long pants. But what if we told you there was a stylish and warm way to take your favorite pair of cropped pants with you into the winter? 

Wearing cropped pants into the colder seasons is not just possible—it’s also fashionable. With a little guidance, you can easily be rocking this trend all winter long. Here’s what you need to know.

Staying Warm

The biggest obstacle to wearing cropped pants through the colder seasons is staying adequately warm. As cropped pants are designed for warmer weather, you can imagine they’re also designed to be ventilated. While we have put together some tips and guidelines for how to wear cropped pants while still keeping warm and stylish, it’s good to bear in mind that these pants are likely not your warmest wardrobe pieces. Let’s see how we can dress accordingly.  

Tights and Long Underwear

One of the easiest ways to hack wearing cropped pants into the colder seasons is to simply wear them over thick tights or women’s long underwear. Thick opaque tights are typically made with a wool blend that works beautifully to keep your legs warm, even if your cropped pants are loose and flowy.

Long underwear is specifically designed to be worn under pants as an extra layer of insulation. Often made of a silk blend, long underwear is perfect for those colder days when you will appreciate the insulation technology it’s famous for. Worried about tights poking out from under your pants? Don’t be! In fact, don’t be scared to even wear a brightly colored pair of tights beneath your black cropped pants for a fun and playful twist to what might otherwise be a somber outfit. 


After a spring and summer of sandals and flats, wearing a pair of boots with your cropped pants may seem a bit strange, but it is super trendy. Wear cropped denim pants with a pair of heeled ankle boots and a cashmere turtleneck sweater for a very chic and sophisticated, down-to-earth look that still keeps your ankles warm. 

Winterize even your most summery cropped pants. Wear your white linen cropped pants over a pair of black wool tights, black ankle booties, a thicker sweater, and a leather jacket. The contrast of styles, textures, and colors is what makes this outfit so interesting and appealing. 

Another way to insulate your legs without having to wear tights or long underwear is to wear your cropped pants over calf- or knee-high leather boots. Wear a pair of loose, wide-legged cropped pants over snug-fitting leather boots to have you looking great and keeping cozy. Style this look with a fuzzy sweater and a women’s wool coat for a great way to integrate your cropped pants into a wintry look. 


Though it may seem frumpy, don’t be afraid to wear socks with your cropped pants and loafers. Not all socks are created equal, and thick-knit, high-quality wooly socks are quite trendy. Style your cropped pants with a clean-looking pair of thick wooly socks and a pair of suede loafers or Chelsea boots. While this outfit tips more on the casual side, it can also be dressed up to look a little more sophisticated. Wear with a chic silk blouse, a tailored wool blazer, and a cashmere shawl to dress this look up a little more. To dress down, wear with your favorite oversized chunky knit sweater for a down-to-earth and street-stylish look. 

All Black

When it doubt, wear black. Sounds boring, but black is truly the answer to most styling problems. Wearing all or mostly black will successfully smooth out the whole outfit. Wear black cropped pants with your favorite black boots and a darker-toned top and coat. The whole outfit will be pulled together seamlessly by the black or dark-colored monotoned. Feel free to break up the black with some bold silver statement jewelry or some brightly colored winter accessories like hats, gloves, and a scarf. If wearing all black allows you to wear your favorite cropped pants for another season, then so be it! 

Enjoy wearing cropped pants all winter long by following these simple guidelines to keep you feeling warm and looking stylish.


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