How to Style Cropped Pants for Fall and Winter

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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

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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.

9 Comments

  • Eleanorjane September 7, 2015

    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!

  • Helen September 7, 2015

    Thank you for the advise! It was very helpful, as your how-to-style-posts always are!

  • Lee4 September 7, 2015

    I’d love some advice on wearing ankle booties with cropped pants. Is it ok? Any tips on how to pull it off?

    • Allie at Wardrobe Oxygen September 8, 2015

      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.

      • Lee4 September 8, 2015

        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.

    • Aimee September 8, 2015

      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.

  • Patricia September 7, 2015

    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…

    • Allie at Wardrobe Oxygen September 8, 2015

      Sometimes and sometimes not since ankle pants are often tapered and could end up having an odd line. It’s very dependent on the boot and the pant 🙂

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