Ask Allie: How to Style a Denim Skirt for Fall

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I bought this denim skirt and this summer I wore it with a T and TOMS but I don’t really know how to wear it now that it’s getting cold without looking like a school teacher. Advice?

Denim skirts are one of those items that seem like a perfect wardrobe staple, but once you have it you realize it’s quite hard to style without looking dated or costumey. A few tips on how to style a denim skirt like this and have it look modern, fresh, and not at all like a school teacher.

This is not the denim skirt you may have worn in the early ‘00s. Back then, I had several denim skirts: distressed, dark and narrow, a-line and short, and everything in between. I went two ways, Lita Ford (would wear with engineer boots and a band tee or tank), or Faux Professional (with a blazer or ribbed turtleneck and knee-high heeled boots… and sometimes fishnets). This go-round with denim skirts, neither is really the trend. The goal, as it has been with fashion for a few seasons, is a bit of a juxtaposition. Hard with soft, dressy with dressed down. This should be in mind when styling your denim skirt.

How to wear double denim denim skirt shirt


This first look has become the hottest way to rock a denim skirt, thanks to Rihanna. Seen this summer wearing double denim with a leather baseball cap and pumps, this is a great way to make a denim skirt look modern and fresh. To make the look better for the cooling temps and to balance the distressed denim, I paired the look with tough black leather ankle booties and a leather wrap bracelet.  Throw a leather moto jacket over it when the temps drop even more.

what to wear denim skirt fall winter


A true juxtaposition is pairing beat up denim with luxurious silk. Balance the roughness of the skirt with a blouse with feminine details. Ruffles, puffed sleeves, or a pussy bow is the perfect pairing; elegant croco pumps and a leopard clutch continue the juxtaposition, making the styling obviously purposeful.

how to style denim skirt fall winter


This final look is the cool weather version of what you’ve been wearing all summer. Switch out the tee for a chunky cableknit sweater or a chic sweatshirt and the TOMS for sturdy boots for a cooler weather casual look that’s high on style and current trends.

Instead of treating a denim skirt like your jeans or denim shirt, consider it an embellished or creative fabric piece. Instead of having the top be the feature, keep the colors neutral so the skirt can take the spotlight.  By changing your outlook on the classic denim skirt, you’ll find so many new ways to style it in a modern way!

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

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  1. Allie, the link for the leopard clutch is going to the wrong link…I would really like to know where to get one. thanks

  2. I haven’t worn a denim skirt for donkey’s years! Now you’re reminding me of the brilliant dark blue A-line skirt with a pleat at the front I got for my birthday when I was about 24 (I think?). I loved that skirt and wore it lots.

    I think my issue is that I’m comfier in jeans in the weekends and my work is too formal for denim. Hence, no denim skirt.

    1. Yep, no denim skirt for me either. I just don’t think it’s the right feel for my office (though at my previous more conservative job I wore the heck out of a dark denim stretch pencil), and it’s not the type of thing I’d wear on the weekend. I will just admire it on others!

  3. I have a J. Crew denim pencil skirt — I think it was called the Farmers’ Market skirt. It’s very stretchy and a true pencil shape with the hem being narrower than the hips, but with a trouser-style front. In the fall I wear it with a Breton-striped shirt, army green military-style blazer, and tan wedges. In the winter, I wear it with a boxy, chunky-knit turtleneck sweater, tights, and boots.

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