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.
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.
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.
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.
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.
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.
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.
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.
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.
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!
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21 Responses
I agree with you about the tall boots with the skirt. Makes such a difference compared to your previous post. I loved both of your looks today.
I like both looks. I bought a black corduroy skirt and already have a denim skirt. I’ll copy both looks. Thanks for the inspiration.
Jo-Lynne,
Do you have a link to the post you did earlier this year where you featured several Jenni Kayne dresses? I remember thinking you looked really good in them but that you did not end up keeping them. I’m in Texas now and hard to justify expensive cashmere sweaters .
Love both these looks, you nailed that effortless cool style. I fully agree that midi skirts need a heel to avoid looking frumpy. I really like the height of the boots you featured. A great way to add height without feeling like you’re wearing “high heels” all day!
I love both outfits!
I like your styling of the skirts, especially the blue denim one. Every time I think about purchasing a denim midi skirt zi have to remind myself how much the length and material constrict when walking or moving and I just can’t do it. You look great though.
Boots are so great, I have a difficult time making denim skirts look right without boots. Sometimes sneakers work. These two outfits look beautiful on you, I’m inspired!
I do need to spend some time creating outfits with my newly purchased denim skirt, so this post gives me some inspiration. Thank you!
Jo-Lynne! I love the midi denim skirt with the boots! Perfect!! We are headed over to the KoP Mall today and I was hoping Evereve would extend their 20% off sale. Grrrrr, one day is not enough. But, I see they have a Kizik shoe store. Have you tried them yet? I am interested in the Milan style, and want to try them on for sizing. Have a great weekend!
Love both outfits! That Vince green turtleneck looks so cozy and comfortable & like the way you’re styling it tucked into the skirt with a belt.
I really like this post. While I like both looks, the black skirt with the teal,sweater and black boots is my favorite.
I really like both looks, but the black wash skirt with the turtleneck looks so chic and sophisticated! I have the items to recreate the second look and will definitely do so.
Hi thanks for the outfit inspiration! One question, do you wear tights with the tall boots with these looks?
I didn’t, but I would if it were cold, esp with the black.
This is the only way I wear my midi denim skirt. It just feels “wrong” without a sweater and boots. Thank you for this post and letting us know about the Jenni Kayne sale!
Beautiful
Love this! I bought a skirt similar to your second one, but with the front slit like your first, in August- literally the first time I’ve had a denim midiskirt since junior high 45 years ago- but struggled with how to wear it in warmer weather. But with sweaters, knee boots, and a green utility jacket I’m loving it.
A little off this topic but it’s cold here now. What brand would you suggest for a neutral/flesh colored tight? I can find black, burgundy, white etc. in stores here but nothing flesh colored. Guess I need to order from Amazon?
How about these or these?
My age is 69, and I find the suggestions great for my body type and age. And the tall boots i truly love. Thanks
You look very nice in both out fits. You look stylish, confident, and comfortable in both outfits. I love a denim skirt with sweaters in the fall and winter.