268: A leather midi is either the single most important fall staple or a complete myth

How to wear Vince's Leather Mid-Rise Pencil Skirt five ways.

I was raised in the ’90s on women’s magazines that would just say anything. Like, just throw out some of the wildest statements so divorced from reality, and there was no thriving internet where you could connect with other people to say, “this is absolutely batshit, no?”

As a curly-haired teen, I was told the best everyday way to treat my ringlets was to straighten my entire head and then recurl it all with a curling iron. Cosmo had me believing couples around the world were regularly engaging in complex sex acts I won’t mention here, and I’m not shy. I imagined office-bound women with a museum’s worth of transformer-like beauty products and purses, all in the name of “desk-to dinner.” And, I can’t tell you exactly where this suspicion came from, but something about the suggestion of a leather midi skirt for fall has, for years, seized on me with the paranoia that maybe I’m still being gaslit by a malevolent, ivory-tower editor somewhere. (And this is the profession I chose, if you can believe it.)

The leather-skirt-for-fall thing is totally reasonable, of course: It’s a heavier-weight material on a breezy silhouette, perfect for straddling the seasons. It’s also very cool—it photographs well and has that Maggie Gyllenhaal in Secretary energy without going full ball gag. The leather skirt attracts and it repulses; I want to wear it, but I’m afraid.

I took a look at Vince’s FW24 collection, which includes, you guessed it, a leather midi skirt. The wheels started turning, and when the conversation of partnership came up, I wanted to challenge myself and my long-held reservations about the garment in a thorough way, once and for all.

This post is sponsored by Vince, which has turned out to be a dream for me. I’ve been wearing the brand since my first year working at InStyle, where they gifted me a cashmere turtleneck that I still own and wear every winter. I always knew the brand was smart and high-quality, but getting to work so intimately with this season’s pieces for today’s content has been an eye-opener. I really hadn’t been giving the brand enough credit for fits, its fabrics, or the very reasonable price points associated with such luxurious end products. They did not ask me to gush like this by the way!

Anyway, the great leather skirt experiment took shape alongside my favorite pieces from Vince’s latest—lots of unctuous silks and warbling knits and papery poplins. I won’t clickbait you into reading all the way to the end to find out that I think I’m pretty sold on the concept. It’s all about the outfits, anyway.

So—leather skirtage, right this way.

Leather Mid-Rise Pencil Skirt, $1,050 / Fluid Satin Bias Pant, $365 / Silk Bias Long-Sleeve Blouse, $425 / Iliana Leather Slingback Flat, $330

Fall layering can be so centered on the neck—frames within frames of variously textured collars and lapels—but that snapshot leaves out the often far more adventurous take on the sport. Hemlines that cascade around the lower eighth, in this case with the leather skirt hitting mid-shin and a pair of viscose pull-on pants draping down to the heel, are a clean way of doing skirt-over-pants without it reading 2002 VMAs red carpet. Not that there’s anything wrong with a bit of oughties nostalgia, this just ain’t it.

Leather Mid-Rise Pencil Skirt, $1,050 / Relaxed Straight Shirt, $325 / Elbow-Sleeve Turtleneck, $165 / Bianca Leather Slingback Heel, $330

Meanwhile, one of the 2020’s defining trends is going to be corporate kink, a reaction to disappearing dress codes in the work place and the misplaced need for authority that was lost with it. Women have always had to pay more attention to the clothes they wear in professional environments because there was never a norm, and so the move became shifting between adopting or subverting men’s suits, depending on the cultural climate.

Now, no one’s even going into an office, and the question of how to look like someone’s “boss” or present powerfully is understandably perplexing. There’s a whole wardrobe to consider, but I like the leather skirt for this job—a nod to the tailored silhouettes that tend to get taken seriously, but unbeholden to the past with a non-traditional material. Most importantly, it’s comfortable so you can keep your mind focused on BUSINESS.

Leather Mid-Rise Pencil Skirt, $1,050 / Double Side-Slit Straight Skirt, $395 / Cashmere Crew Neck Sweater, $325 / Alina Leather Heeled Thong Sandal, $295 / Jumbo Straw Tote, $395

Leather skirting for summer people: A net bag that carried you through farmer’s market season (or in which you transported every shoe, accessory, and sweater shown on this page) suddenly becomes the perfect apple picking companion. Block heels from Fort Greene Park days walk their way over to Storm King on a crisp afternoon (probably on a third date). That romantic whisper of a skirt you wore with barely more than a tan…now it’s a slinky detail beneath the leather midi protecting you from the elements finally making their presence felt.

Leather Mid-Rise Pencil Skirt, $1,050 / Pearl-Button Wool-Blend Cardigan, $325 / Naomi Leather Loafer, $330 / Chimi 04 Sunglasses, $160 / Cotton Linen Pouch Bag, $295 (below)

If I was Joan Didion (how’s my impression, by the way?) my packing list would look something like…

To Pack and Wear:

2 skirts (1 leather, 1 slip)
2 jerseys or leotards
3 pullover sweaters
2 button-up shirts
5 pair shoes
pull-on pants
bra
nightgown
robe
slippers
cigarettes
natural wine

Leather Moto Jacket, $1,395 / Leather Mid-Rise Pencil Skirt, $1,050 / Wool-Blend Polo Sweater, $295 / Dylan Leather Criss-Cross Slide Sandal, $275

There are folks who can pull of a Canadian tuxedo. I am not one of them, but this? This I feel pretty good about. I appreciate the restrain of this jacket—where it’s held back on the snaps and cross-zips that make many motorcycle jackets look like James Dean cosplay, it’s added dimension back in with texture. It ultimately comes back to the feel of the leather, which, as with the skirt, is soft and flexible like a heavy satin that gives it that incredible drape.

Leather in general can swing so wildly across a spectrum of stiff to buttery, the biggest caveat I have to add to this piece of stunt journalist is that the ease and comfort I found might not be replicable through a lesser version. If I ran this test with a stiff, crunchy tube that pinched my waist and stopped me from sitting down, I might not be so keen to put away my leather-skirt anxiety. Thank god for Vince, though.

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