I Tried On 48 Different Skirts In 2 Weeks. These 4 Will Still Be Great In A Decade.

They all pass the versatility and longevity test. That's a thing, I swear.

Hi everyone, and welcome to October. Before we get started, just wanted to check: Are you registered to vote? It’s worth checking, just to make sure. And if you haven’t voted in the past, you are not alone. It took me a shockingly long time to participate in the voting process, but I’m not big on shame so I try to look at it as: Better late than never. And yes, I know that this simple opening statement will cause some folks to unsubscribe and get annoyed with me, but I’m at peace with it. 

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As for today’s story, you know I’m a skirt person, so it’s probably no surprise to hear that I’ve been on a bit of a skirt bender. In fact, I’ve tried on at least 48 skirts over the past few weeks, at just about every price point imaginable, to come to four I’m showing you today. 

The reason I like skirts so much is they’re more versatile than most folks imagine. Depending on the weather, you can go bare legs and loafers, add opaque tights—Commando matte opaques are my go-to because they never cut in, nor itch, and they’re made in Vermont!—and a flat boot when it gets brisk, and then throw on a suede over-the-knee boot for maximum warmth. 

I also like pieces that can be dressed up or down easily, and skirts do this in spades. A silk maxi skirt can look chill with a vintage t-shirt and your preferred sneaker, polished with a kitten heel and a cardigan for a creative office, and champagne ready with a delicate stiletto, tux blazer, and more formal clutch for evening. To me, that type of range is the hallmark of a wardrobe item with true longevity. And wardrobe items with true longevity make you feel great. And we should all feel great in our clothes, period.

So with that, I’m going to transition into the actual story. While outfit selfies are not my love language nor my comfort zone, you have all been so kind about it whenever I post them, so here you go. Four skirts, five looks, and a whole lot of details. I hope you enjoy.

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J.Crew Seamed Circle Skirt ($248) in Dark Carob faux leather 

• Gap Merino Sweater ($35) in Terra Brown + Isabel Marant Piery Slingback Pumps ($980) in leopard print + Saint Laurent Kate Tassel Bag ($2250) in wine velvet

Fall is leather skirt weather, and I really like this dark brown faux leather skirt from J.Crew. I know it looks almost black here, but it’s not; it’s closer to chocolate, with just a hint of red mixed in. It runs true to size, is shockingly lightweight, and looks elevated IRL. Styled it as I usually do, with a very thin wool sweater; this one is my go-to style from Gap that I’ve been banging on about since last fall. 

The shoes are a low heel slingback (yes, my favorite) that you’re going to be seeing a lot of this season because I have no plans to take them off. Leopard or animal print is really hard to get right, so when I see a brand doing it flawlessly, I tend to buy it immediately. These heels are very low, very kitten, and extremely comfortable and elegant. I bought my heels at Net-A-Porter, but they seem to be low in stock; Isabel Marant’s website has a full assortment as of writing this. 

Bag is, you guessed it, nearly a decade old,  and you can find the exact dark wine velvet version on The Real Real or other resale sites.

What am I looking at? I’ll never tell.

 Ulla Johnson Enid Paneled Leather Skirt ($1250) 

• Carven Vintage ‘80s Pinstripe Shirt ($50) + Chloe Embellished Suede Shoulder Bag ($3290) + Isabel Marant Piery Slingback Pumps ($980) in leopard print 

My friend Jerrica recently opened an incredible online vintage store—NYBRED LA THREADS—and I bought this perfect pinstripe shirt from her, seconds after I landed on the site. It was made by Carven for Air France in the ‘80s, and it’s flawless. Her eye, taste, and curation is dangerously good, you should visit immediately! 

The skirt I got in New York when I was there for work recently. I love the shape and length, and didn’t have anything like it in my closet. Plus it feels like a dream to wear. This is how I would style it for work; looks profesh, no? She’s versatile though, as I demand of my skirts! On that note, I wore it with a shrunken lace knit cardigan from Madewell for date night, and an amusing Re/Done 90s print recycled t-shirt for dinner with a friend, and was happy with the results both times.

As for the bag…I’m deeply into what Chloe’s Creative Director Chemena Kamali is doing for the brand right now, and I ended up investing in this two-for-one suede bag for fall. Yes, it’s two bags in one. You can either wear it the way I have it here, as a shoulder or crossbody boho bag, or you can remove the leather strap and attach the circular bracelet top handle to wear it in a more evening type of way. I also love that it’s suede, which I think looks nicer with a leather skirt than leather; velvet would obviously work too. 

Again: I bought my heels at Net-A-Porter, but they seem to be low in stock; Isabel Marant’s website has a full assortment as of writing this. And glasses are prescription Caddis Mabuhay Frames ($340) and come in three other colors. 

Ulla Johnson Enid Paneled Leather Skirt ($1250) 

• Alix of Bohemia Priscilla Smoke Smocked Blouse ($860) + Chloe Embellished Suede Shoulder Bag ($3290) + Isabel Marant Piery Slingback Pumps ($980) in leopard print 

Another way I’m wearing this skirt? With the most phenomenal hand smocked, hand embroidered blouse I have ever worn. When I tell you this is a piece I will wear and treasure for decades, I mean it. It’s beautifully embellished, and I love the details on the collar and the cuffs. It will also look amazing tucked into my new vintage Levi’s 517s from Jean Genie Vintage, which I discovered from Jane Herman’s incredible Substack, Jane on Jeans. (If you aren’t a subscriber, you should be; I don’t think there’s a single woman who knows more about jeans and is an incredible writer.)

If you don’t know Alix of Bohemia, you probably should. There are so many incredible pieces; I also have my eye on the Annabel Raven Dot Silk Shirt ($460) and the Kiki Noir Rivera Shirt ($390) gives me Jim Morrison vibes in all the non-toxic ways. 

Accessories are the same; just wearing the Chloe bag in the other configuration! 

I am really into this Chloe bag. Like, I think about it all the time. And I thought about it for well over a month before purchasing.

J.Crew Gwyneth Pleated Slip Skirt ($128) in Woodland Dusk

• Velvet Violette Blouse Cardigan ($198) in Forest + Isabel Marant Piery Slingback Pumps ($980) in leopard print 

Full confession: I am apparently powerless to stop writing about this skirt. I have it in black. I have it in navy. I love it in this weird olive/brat green. I generally think it’s true to size; I have both a small and a medium, and am wearing the small here.

If you aren’t in to the shade, I’m happy to say there are other options for creating a tonal look. Plus, the black, navy, silver, and camel iterations of the skirt skirt are over 50% off right now Or you could do the skirt in vivid burgundy with a cable knit cardi, which is on sale now too. Or the navy skirt with a featherweight cashmere shrunken cardi, also good, or there is a Tencel cardi in a really nice shade of camel that would work with the camel pleated skirt. 

As for the cardi I’m wearing, she is so soft and yummy. I went up a size (in a medium here) because not every cardi I own needs to be shrunken, and I’m glad to have something a little slouchy. 11/10 recommend. 

PS: I think it’s also cute layered under my written-about-1-billion-times oversized Khaite Ross Denim Jacket ($980), which I wear approximately four days a week just because I’m determined to justify the price per wear of it all. (For the record, the retail price has gone up since I bought it.)

Reformation Bella Silk Skirt ($218) in Pluto Dot

• Michael Stars Celeste Crew Neck Cashmere Sweater ($268)  + Coach Brooklyn Shoulder Bag 39 ($495) + Jimmy Choo Amita Slingback Pumps ($875; mine are older and a slightly higher heel, but these are quite similar)

Oh I’m going to wear the hell out of this outfit. First of all, the skirt is wonderful; simple, elegant fit, and a weirdly great price point for the quality. I’m wearing a medium and honestly am going to size down; I think she runs a smidge big. I assume this is old Burberry runway and Vogue editorial memories surfacing, but I love a maxi skirt with a super soft and cozy cashmere sweater. The kind folks at Michael Stars sent me this one, and honestly I’m buying more this week. I like the idea of a more cropped fit with the maxi skirt, or to go really oversized and slouchy.

IMHO, the skirt is also oddly versatile. You can wear it with a sweater, simple heel or even a little loafer, and an excellent oversized boho bag, like my go-to Coach work bag shown here (yes, you can fit a whole ass laptop in there, and more. Mine has one of Wilder’s sweaters, an Octonauts book, my makeup bag, a clutch, and my wallet in it here, and you’d never know.

I regret to inform you it comes in many other colors.

You could make it more evening by pairing it with a more standard heel—Gianvito Rossi’s elegant options are always great for me, especially in a 70mm height—and that Chloe bracelet bag I love so much. Or you could go for a really stompy moto boot and under the world’s greatest field jacket? Just saying. 

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Okay friends, that’s it for now. If you want to follow me on @hillarykerr, I’d love it. And if you have anything to say or ask (preferably nothing terribly mean), please drop me a note either via DM or in the comments below.

As always, thank you for taking the time to read this post. I’m truly so glad you’re here. If you like what you’re reading, please consider sharing this newsletter. (And if you have the time to like it, that would mean a lot to me!) All products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated.