How to Wear a Denim Skirt This Fall

Happy Friday, friends! I’ve got an old-school outfit post for you today. We’re talking about how to wear a denim skirt this fall, and I styled two denim skirts using the same outfit formula — a black wash denim midi pencil skirt and an A-line midi skirt in a medium indigo wash.

How to Wear a Denim Skirt This Fall

Vince raglan wool/cashmere turtleneck (S) (also at Nordstrom & Neiman’s) budget options here and here // Gap Factory denim midi pencil skirt (29) // Dolce Vita boots (8) // FRAME belt (M) // Jenny Bird earrings // Victoria Emerson bracelet // YSL sunnies // Quince box bag

I’ve had this black wash denim skirt for quite a while, but I didn’t love the way I styled it the first time in this post. The color palette works, but I don’t care for how the waistband of sweater sits on the skirt. Plus, the low profile pointy toe flats don’t balance the bulk of the sweater/denim skirt combo, and I feel like midi length skirts look better with more of a heel.

How to Wear a Denim Skirt This Fall

Gap Factory Roll Neck Sweater (S) // Gap Factory Denim Midi Skirt (29) // Sam Edelman Cohen Flats (8.5)

I do really like this skirt, though, so I’ve been wanting to try it again with boots and a different sweater. The front patch pockets are a fun, trendy touch, and the midi-length pencil-style silhouette is slenderizing. It’s also a great price, and it runs true to size; I have the 29.

How to Wear a Denim Skirt This Fall

I like denim skirts with sweaters in the fall, but this time, I paired this skirt with a sweater that isn’t quite as bulky as the stripe roll neck sweater. This is the Vince Wool Blend Turtleneck Sweater in Sea Onyx, which I managed to snag on sale a while back.

It’s pricey, but Vince sweaters stand the test of time, and I fell in love with this gorgeous shade of green. It’s made of a mid-weight, fine-gauge wool/cashmere blend, and I love the raglan sleeves and the ribbed turtleneck that stands up easily but isn’t too tight or too tall to be uncomfortable.

How to Wear a Denim Skirt This Fall

For size reference, I would say this sweater runs true to size, or size up if in between. I’m almost always a small in Vince sweaters, but this year, I’m finding myself more comfortable when I size up to medium, which is what I’m wearing here. I think it’s a me problem, not a Vince problem, so do with that as you will!

If you want a lower priced option, I found this SoSoft Turtleneck Sweater at Old Navy, and Everlane has this Boxy Turtleneck in Everyday Cotton.

I debated incorporating a shade of brown into this look with my choice of footwear, but at the end, I went with the more predictable black. The rich black suede of these Western-inspired Dolce Vita boots creates a subtle contrast against the washed black denim, while keeping a cohesive color palette.

How to Wear a Denim Skirt This Fall

I added a belt and some simple jewelry to complete this look, and I carried the black Quince box bag. I wish I’d taken a few photos with the bag worn crossbody. I feel like wearing it that way adds a point of interest to the look, plus I’d like to share a better picture of this bag! It’s a really classy piece, and the price is great for Italian leather.

How to Wear a Denim Skirt This Fall

This outfit stands alone just fine, but it will look even better with a long wool coat on top, or I could even wear a leather bomber for an edgier look.

How to Wear a Denim Skirt This Fall

Another variation on this look is one I styled last spring, with this Rails denim midi skirt. This time I went for a neutral look with an ivory fisherman sweater and caramel suede boots.

How to Wear a Denim Skirt This Fall

similar sweaters – splurge and save // Rails The Highland denim midi skirt (29) (more sizes here) // similar Sam Edelman boots // Clare V Midi Sac // camel suede belt (M) // Tom Ford sunnies

This was a wool/cotton blend sweater from Nordstrom that has since sold out, but the Quince cotton fisherman is a good option, or the Jenni Kayne cashmere fisherman is 25% off right now with code EARLY.

I accessorized with gold jewelry this time, and I’m so happy to see this Clare V Midi Sac is still in stock! It’s such a fun little bag.

How to Wear a Denim Skirt This Fall

My Sam Edelman knee boots are from last year, but they have a similar style this year, and they come in regular and wide calf sizes.

There’s something about the denim midi skirt, front-tucked sweater, and suede knee boots that create a really pleasing balance of proportions. Even if these exact pieces aren’t all available, you can recreate this look with similar styles. I hope it’s helpful if you’ve been struggling to style a denim skirt this fall!

How to Wear a Denim Skirt This Fall

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