One of the things I love about getting older is leaning into the hunches we have about the things we want to wear. This occurred to me about a year and a half ago when I was walking down the Promenade in Brooklyn Heights with my friend Shelly and I noticed more people than usual looking at my outfit. I was wearing a long vintage silk striped Anne Klein skirt, a vintage football jersey, and white Birkenstocks. I came home and did a tiny Reel because I wanted to remember what I was wearing. Specifically, how I wore that skirt.
I think for most of my life, and maybe yours, too, skirts have confounded me. They are not only politically/societally loaded with all manner of cultural stereotypes, from fifties housework and the women’s movement to endless “school teacher” riffs. Cinematically, (some) long skirts have become historical, too. In particular, Molly Ringwald in The Breakfast Club. She wore this head-to-toe Ralph Lauren look nearly 40 (?!) years ago, and it’s still burned into my sartorial psyche.
What’s so good about this look and makes it so interesting to wonder about all these decades later also happens to be at the core of Ultimate Skirt Sorcery—it defies all that we know about age, time, and trends. I’ve never forgotten that outfit, and I was reminded of it recently when I was looking through the Fall/Winter Prada show. SO many AMAZING skirts descended directly from heaven…sheer ones, long ones, festooned ones. Mrs. Prada is perhaps the Ultimate Empress of Great Skirts, and honestly, we could probably skip this newsletter altogether and just spend the next seven minutes looking at pictures of her for inspiration.
Photos courtesy of Prada.
What Mrs. Prada likely knows, as well as Claire Standish, and anyone else who has worn a skirt to great effect is this: They are unaffectedly liberating. From style rules to bodily restrictions to how/what to mix them with. I posted a teaser about this story yesterday in my IG Stories and I got a ton of DMs, mostly from people who already knew why/what I’m talking about/celebrating here. Which is that skirts secretly have sweatpants attitude. It’s TRUE. You can do ANYTHING in them. You can wear them with heels or boots or sneakers. You can wear them to work or to a wedding. You can even do yard work in them, as one woman named Chanel told me via DM. (I love her.)
And yet, with seven or so long skirts in my closet, I always hesitated about how to wear them…until now. Something clicked for me this year that makes me want to wear them ALL THE TIME. And I’ve been buying a bunch on eBay (here, here, here!) because honestly, so many of them are just better and more interesting than new skirts. By all means, if you can afford one from Prada, DO IT. And if not, head to the back of your closet and pull out the one or five you might have but haven’t worn in a while like I did.
What’s ahead are more considerations than rules. I don’t wear short skirts, but by all means, gives yours a whirl with some of these thought-starters. The most important point to sustain you is that a skirt pushes us to experiment. To PLAY. To challenge ourselves with shapes/proportions/occasions and expectations. When I look back at that Football Jersey/Anne Klein skirt combo, I know it’s weird. But I don’t care…because it just felt good and right for me. When it comes to skirts this spring/summer/into fall, I hope you’ll do the same. And in the wise words of Katy Perry, “No regrets. Only love.”
Okay, let’s get into it…
SPORTY WITH SOME TAILORING—I love all the sheer skirts we’ve been seeing lately, but for me and my resplendent thighs, there is just no going full sheer. I do however like to wear biker shorts with any of my sheer skirts. This one is vintage raffia from the ‘60s, which I found thrifting in NYC in the early aughts with my friend Erin Wylie over at Black Bird Spyplane. Here’s a similar one I found on eBay that’s even a little longer. While back in the ‘50s/’60s this might have been worn in a more formal way (probably with a hat!), I like dressing it down with a pair of Suicoke sandals and a striped tank (which would look good layered under any of these skirts). The jacket is this silk-like bomber on sale (that I have been wearing under and over things nearly every day), and the bag is by Max Mara, but I also love the one Leandra Medine Cohen designed recently with Soeur…both are cross-body which is KEY. Glasses are vintage Liz Claiborne that I’ve had for about 25 years…I am NOT kidding! For $40 I love these, too.
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LUNCH OR DINNER?—Building on the striped tee and the navy silk bomber, I added in this button-up embellished skirt by Rodebjer, one of my most favorite designers ever. Carin Rodebjer is an expert when it comes to skirts—this one, this one, and THIS one—and I’ve worn this one both as a top under a blazer (over pants of course), and as a skirt with black tights and knee-high boots. I also LOVE this one by La Double J. Having a skirt like this in your arsenal offers lots of experimenting…and it literally will NEVER not be in style. Bag in this sublime soft mushroom shade is by Little Liffner, a Scandinavian brand of accessories made in small family-run Italian factories (I love their jewelry, too!); the pants are Old Céline, though I might also layer this skirt over these Everlane Dream Kick pants. Sandals are old Zara but these are quite lovely and a great price, as well as these by Madewell. Shades are Old Céline, too. A touch fancier, I also tried this look with a different vintage (J.Peterman) blazer that I found at Brimfield last season and a vintage gold bag I found thrifting Palm Springs last year (this similar one by Stella McCartney is SPECTACULAR and could be worn a million different ways). Here’s a Paco Rabanne-style vintage option, too, that’s way cheaper. Last thing: A skirt like this fringey vintage YSL, would look amazing with this look, too…it’s 🤯.
EVERYTHING I/YOU NEED IS RIGHT HERE—Here we go with trying to recreate the energy of that football jersey look. And this one is really at the heart of skirts this spring/summer—wear them with something giant on top that creates contrast in a good way. I thrifted this vintage silk Ann Taylor skirt a few years ago and I’ve worn it a ton, mostly with big sweaters or sweatshirts to offset the more formal vibe it was probably born with (here’s a same-vibe version from Madewell). If I had a rule book, which I kind of do/don’t have, it might lead with something like, Never Go Full Fancy. I’m always much more festive-feeling and comfortable if I make a formal piece a lot less fussy. The sweatshirt is vintage Ton Sur Ton (a grail FAVE), the bag is classic use-it-forever quilted MZ Wallace in navy, which is definitely my new black lately. Speaking of navy, I love this long silk Banana Republic skirt a whole lot, too.
GIVING 1920s TENNIS VIBES—With an oversized gray sweatshirt (wear this Everlane version with EVERYTHING and tie it around your neck/waist/etc. tooooo!) and simple white SeaVees court shoes (most comfortable on the planet…I walked about four miles in them yesterday, so I know this to be true:). Bottom shot, with my beloved Sézane Will jacket, which has been my off-duty “blazer” of choice.
SOMEWHERE ON GOOFBALL ISLAND—It’s breezy, it’s easy, and as long as you bring along your very cool trademark sunglasses, you’re going to cook up some BIG magic here. Below, this skirt is very passionately homemade (found on eBay) and I just love it. It definitely has some Dries DNA in here, right? Given this one is a circus no matter how you slice/wear it, everything else needed to be a bit more neutral for the backup harmony. In this case, a vintage Gap waffle t-shirt layered under a boxy white t-shirt, which is the right balance to offset the slimmer/swingy skirt shape. In general I am a big fan of long, full striped skirts (especially when it’s warmer out)…so if you don’t have one yet, might be an opportune time to add it to your list. And definitely add Vintage Striped Maxi Skirt to your Watch List, too…cuz you never know what might pop up…🦄
This skirt makes me happy. Clearly.
Max Mara bag again…such an all-around winner. And thanks to Becky Malinsky for tipping me off about it…makes me happy every time I see it in my closet.
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A SKIRT + HEELS MOMENT—In general, I don’t love a heel with a longer skirt. But I realize many of you out there appreciate a little lift from time to time, so I tried this one out for kicks. This lace chevron skirt is from at least five years ago from the Australian brand Macgraw. I love a lot of their stuff including this sequin skirt, which could be worn in a similar way. Pairing a long skirt with a long menswear stripe is definitely my thing, so if you still don’t have a shirt like this to wear into the afterlife, what are you waiting for? Blazer coat is old Zara, but this one is wonderful, too, as is THIS and this.
SMART/SEXY TEACHER VIBES—Okay, so here’s an example of a vintage J.Peterman skirt I bought on eBay that I LOVE but don’t necessarily love on ME. It’s a size 10 (albeit a vintage 10, fits more like a 6/8), and while I really love the idea of it and especially the dreamy shade of camel, it’s a bit too…mmmm, preppy for my kookier inclinations. I tried it out a few different ways: With an embellished Rachel Comey top and COS knit shirt/jacket, and this SPECTACULAR Anthropologie ❤️ bag by Simon Miller, with a vintage silk striped shirt and vintage Prada bag, and also with just a simple white button-down (gold heels are also vintage Prada, but these are GOOD, too:). I think if you have a similar beloved school teacher-vibey skirt like this in your closet, this is likely how I’d wear it. I tried it also with vintage loafers but it was a little TOO on the nose for moi. That said, if anyone wants this skirt, DM me or message me through the Substack app…I’m sure it’s perfect for someone and maybe that someone is YOU…
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Where do I start? I was talking with a big collector of collectibles the other day and he thinks that Ferris Bueller's vest was THE clothing item of the mid-80s movies and I said no way - Molly Ringwald's outfit in The Breakfast Club for any woman of a certain era!!!
That said, I have always been a skirt person - you put it perfectly when you related them to sweatpants! I travel in a skirt - my fave for a few years is a long sherbet colored striped knit skirt as it works just as well with sneakers and a t-shirt as it does dressed up for a work meeting with a blazer. Tights or bare legs - another thing that makes skirts so flexible for all weathers and a travel/comfort staple. But mostly, I love the flexibility and ease and the sense of wearing something different and slightly special. And maybe for me, it's just that my body shape looks so much better in a skirt than pants?
This is SO GOOD as ever Christene - invigorating spring vibes! Just what I need for inspo. Thank you 💚