How to Style Cropped Pants for Fall and Winter

This article may contain affiliate links; if you click on a shopping link and make a purchase I may receive a commission. As an Amazon Associate, I earn from qualifying purchases.

This spring/summer I bought two pairs of cropped (ankle length) pants. One is a pair of skinny black jeans and the other a pair of burgundy tapered slacks. I've worn them with flowy tops and sandals or ballerina flats and now I wonder how to style these pants for fall/winter. The colors and material will work very well for those seasons, but I'm at a loss of how to style them. I'm a size 16 and a bit self-conscious about my hips in skinny/tapered pants but I really like these two and would like to be able to wear them when it gets colder. I'm a university student, so style is casual, but I'm in my 30's so I want to look a bit more put together.

Ankle pants are tricky, but not impossible to style for fall and winter. I’m glad you brought up the colors and materials of the cropped pants, that is the first step into determining whether they can truly transition into colder weather. Chino is iffy, cotton sateen is too summery, and I’ll wag my finger at anyone who wears seersucker or linen crops come fall (unless you’re in a tropical locale!). But denim, stretch twill, ponte, and other thicker fabrics with a tight weave can transition quite nicely.

how to style cropped pants for fall and winter

Shop Similar Looks: Jeans | Pants | Turtleneck | Striped Sweater | Gray Sweater | Leopard Flats | Burgundy Flats | Black Flats | Tan Flats

The easiest way to transition cropped pants into fall is to do what I call, “Channeling Audrey.” Known for her sleek look with flat shoes, cropped pants, and a turtleneck, using Audrey Hepburn for inspiration is a chic way to make ankle pants look seasonally appropriate when the temps drop. I don’t recommend this look for winter as the effect is ruined when you add hosiery; while your ankles may be bare it is balanced for milder temperatures by the sweater on top. A blousy or slouchy sweater will ruin the effect; to balance your hips consider creating volume on top with a boatneck, turtleneck, or horizontal stripes. As for the flat, one with a pointed toe or teensy wide heel will also provide balance.

A fall work alternative is pairing the cropped pants with closed-toe pumps in a dark color. Style the pants as normal; such a slim fit looks great with a boyfriend blazer or longer cardigan.

how to wear cropped pants into fall and winter

Shop Similar Looks: Jeans | Pants | Boots | Sweater | Blazer | Wrap | Tee | Striped Top | Turtleneck

The best way to make cropped pants work in winter is hide the fact that they’re cropped. Since both styles are skinny, they’ll slide into a pair of tall boots quite nicely. Layers will also add to the wintry feel; a boyfriend blazer, sweater coat, or wrap will hide your hips in a seasonally appropriate fashion and the boots keep your figure from being too top heavy.

If these pants “feel” like summer and you have to work really hard to style them in the colder months, it’s best to store them and not wear again until spring. While it’s tempting to “make it work” with summer pieces to extend your wardrobe, it’s not worth it if it sacrifices your style. A woman’s style is not determined by the size of her wardrobe but how well she knows her style, her body, and the situation at hand.

A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

Did you like what you just read?

Consider tapping here to buy me a coffee in thanks. The best gift you can give a content creator is the gift of sharing. Consider sharing this article on Facebook or Pinterest. Thank you so much for your support!

Similar Posts


  1. I just avoided buying cropped or 7/8 pants this summer as it’s usually not even warm enough in summer for them, let alone autumn! I do wish English shops would stop trying to sell really lightweight clothes when we only really need them when on holiday in Spain!

    1. This is really tough to offer virtual advice as there’s no tried and true. It has a lot to do with the cut of the pant, the height and cut of the boot, the shape of the leg… best is if the pant is super straight (which is likely isn’t if it was purchased in the past couple of years) and the boot is short enough to have at least some space between pant hem and boot top. But there’s too many variables to offer legit across the board advice.

      1. Thanks! I do see that it depends on the pants, so I’ll play around with this some. I’ve gotten 2 pairs of booties at DSW recently & just want to make sure I wear them a lot (they are so cute!). One pair is a very traditional Chelsea-type black bootie so maybe the lowness of it on my ankles will give me some options.

    2. I agree with Allie’s answer below. I think it is a cute look but really does depend on all the variables she mentioned. You will just have to look in the mirror and maybe ask a friend. I pulled it off last year and loved it, but decided to get rid of the jeans because they were embellished with rips and some sequins that just weren’t right for me. I have a feeling I won’t be able to find the right elements again, but I will try.

  2. I wear ankle booties with straight leg pants I’ve rolled to above the ankle. would that same look work with an actual ankle length pant? If so, another option…

Leave a Reply

Your email address will not be published. Required fields are marked *