Hi! I rewatched Nora Ephron’s When Harry Met Sally last week and was inspired mostly by Harry’s ‘70s—’80s fuckboy outfits—I thought to rank them, but Sophia Benoit at GQ already did that a godforsaken six years ago. I also kind of abhor the intensely minimal, generic way ‘80s style especially is watered down in Ephron movies—I get that it makes the characters feel more like everymen and keeps the focus on their relationships and acting rather than creating a Wes Andersonian tableaux, but I personally think the widespread call to dress like a Nora Ephron character every autumn and winter might be under-the-radar quiet luxury propaganda. With that in mind, I played around on Pinterest (the board with all of its sources is linked far below!) and, using Harry and Sally as a starting point, pushed Ephronian fashion to far weirder, sexier, and more compelling heights in four categories ranging from least to most casual. From pillbox caps and statement belts to leggings tucked into socks and the return of the shorts-over-pants, this post has an immense amount of inspiration that will hopefully help us all get through the fall and winter—I’m already feeling the gloom, scarily enough. Please feel free to share the parts of your wardrobe and/or other facets of your life that make you happiest during the cold months in the comments! Asking for a me!
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Sellout Segment
Before we begin the main event, I have decided that I’m going to try and include a few items every week that I either genuinely want or recently purchased with my own $$ in an effort to be more consistent with my affiliate links without being a total monster and compromising the quality of my blog, most of which is, as you know, centered around more abstract content and secondhand or DIY buys. I will always provide rationale for my recs and they will never be behind a paywall—even just clicking them helps me in my efforts to start getting free stuff from companies I’ve been giving free PR to for going on 5 years now, so your attention is much appreciated (and the stuff I’m including is actually cool and/or useful—no $890 fuckass jelly flats here, thanks)!
I HATE that Le Bon Shoppe’s clothes are so non-inclusive—it’s ridiculous that there are only three sizes of these pants and that the largest is a size 8 or 10 at most. It’s honestly offensive. For better or worse though, these pants are the perfect shape, easy to wear, hardy, and I find myself reaching for them in the cheetah and black colorways often (I usually buy from ban.do, linked).
That stupid Elvive shampoo and conditioner everyone’s been saying makes your hair grow like the dickens did nothing but make mine dry, tangled, and crunchy-feeling. I went back to my ol’ faithful SheaMoisture but this time tried their newer, ostensibly more hydrating formula, and it literally fixed my hair in one wash.
I want to try Chris Collins so badly, especially his Long Kiss Goodnight and of course, African Rooibos. $25 for five scents is a great deal for 2ml samples, and I think this set is exclusive to Sephora, so I’m really hoping it comes back in stock soon. I’ve heard only good things and I love what I’ve read about these scents—if anyone wants to send me some samples, I’d be much obliged and I’ll review them on the blog + give you a comped subscription!
Put-Together
This might be the first time I’ve fallen in love with a brimmed felt cap, and tragically, they barely exist beyond the bounds of Nora Ephron and W**dy A**en movies—I suppose the style is like a bowler with a wide brim? Essentially the only comparable piece I could find online was this exact replica on Etsy:
The shop, lyndahats, is a gem I’m thrilled to have found, with fairly movie-accurate chapeaus from films like Breakfast at Tiffany’s and Annie Hall in various colors and materials. From cloches to sunhats, Lynda has us covered for a price that, while steeper than I can afford right at this second, makes sense for an investment piece that you won’t part with until you croak.
A pillbox hat or beret might be easier to find than the hat above, and velvet (WITHOUT the little sticky-outy-thing that makes berets look kind of silly) is a nice alternative to felt. The other most essential accessory to elevate an ‘80s fall/winter look is a graphic, geometric belt. This diffuses the look of high-waisted pants if you feel like they make your torso look too short. A thick belt in a similar color to your top can essentially artificially lower your waistband.
The tension of brown accessories over a simple black trench livens it up beautifully. Throwing a belt on over huge, bulky outerwear essentially transforms a trench or other type of coat into a full outfit.
Matching the color of a solid-colored scarf to the jacket worn under it makes it look like one garment, giving it a look that’s both futuristic in a Dune fashion and retro in a Jackie Kennedy way. The velvety navy pants paired with the chocolate brown might be a color combo that’s been done to death the past few years, but I still find it really inspiring!
Here’s another example of a pillbox cap done right, shockingly matched with…culottes? The culottes with the V-vamp heels create a gorgeous, arrow-like swath of skin that makes the entire look feel floaty instead of too stiff with such a structured hat.
I’ve never seen this buttery tan done as a monochrome, probably because it would be a horror story to find a clean place to sit that wouldn’t result in some kind of wardrobe disaster. However, this is the perfect way to pull off a goofy pom-pom cap: make it part of a monochrome look. I’d do this in navy, dark purple, or brown to save myself the agony of stains.
Contemporary Examples
Judith of Style Crone uses two of the accessories discussed above, a pillbox hat and a wide belt, to make a look with a denim jacket feel downright formal. The dual-toned scarf taking up the space between the chin and the V neckline adds an immense amount of energy to an otherwise slightly stiff outfit.
A bit more of a youthful take on the pillbox cap leans upon small-lensed sunglasses, a long, boxy coat, and suede accessories. The subtle color contrast of maroon and eggplant is a very advanced move.
Casual
If Sally’s jeans re-make the case for a high waist again after a few years of me abhorring any pants that dare to creep even close to my belly button, Harry’s jeans confirm to me that a mid rise is unimpeachable (and go check out what I wrote for
about jean fly length—Harry’s is the platonic ideal). This fall, I am just as devoted to the belt in a casual fit as I am in something more formal, especially something in the brown family, preferably somewhere from caramel to russet.
I love that cardigans can just be worn as shirts. I think of a cardigan as a knit button-up, essentially, and usually regret putting them on over something as opposed to just wearing them alone. I think Sally would shop Nikki Chasin in 2025 for its boxy fits and large disk buttons. The loud colors might spook her, though.
This Meg Ryan fit is 1000x better than anything Sally wears in the movie, with appliques outlining her dark cardigan, a just-too-high rise on her trousers underlined by a weirdly low-placed belt and gorgeous, full pleating at the thighs, and scrunchy socks with zip-up shoes. It’s the only photo I can find of this outfit, but this single handedly opened my heart to the high waist on pants that are not jeans.
This is a much more chill, easy version of the above outfit that could easily be put together with Gap basics and thrifted trousers—the key is for the sweater and trousers to be grayscale but the belt and shoes must be brown. It’s just the tiniest drop of perverse tension in an otherwise too-prim outfit. Here’s the Gap cardigan everyone loves right now:
And here’s a new 100% cotton, thicker-knit one I like better, though its arms look weirdly long, so keep that in mind if your limbs are on the stubby side like mine:
Note that if a cardigan hits anywhere above your natural hips, you’ll look like you’re in Bye Bye Birdie, and if it hits anywhere below, you’ll look like a substitute teacher. I’m very serious about how delicate this line is to toe, so try these on in person if you can.
On the more coastal side of fall wear, I’d never thought of layering a denim jacket over a blue top of the exact same shade. The brown belt plays an essential role again, making the stripes feel collegiate and preppy instead of childish. This look would work great with white sneakers or light-ish brown boat shoes, too.
Major belt + tying tulle around your neck to fill in the space of a deep V neckline without the added weight and warmth of an actual scarf is something I have to do this season. By the way, the best belts ever are Brighton, and there are tons to be found secondhand online. I saw one in person at the store I work at and it was high-quality and gorgeous.
Whoopi Goldberg is one of the best fall/winter dressers, bar none, case in point her layering a thinner, patterned turtleneck shirt under a chunky, folded turtleneck sweater that *just so happens* to match her headphones. Matching headphone to sweater or jacket takes an outfit from simple to extremely advanced in one fell swoop.
If Sally ever dared to smoke a single cigarette, I could see her pulling a Parker Posey and tucking a bright red flower (and… an envelope?) into a trench coat or peacoat along with a neck scarf.
Contemporary Examples
I hardly ever see a) a scarf OVER a jacket, b) a scarf over a LEATHER jacket, or c) this kind of tapestry scarf in a more masculine outfit. The well-worn bomber jacket perfectly brings out the buttery undertones of the leather, the greenish corduroy pants set off the olive tones in the scarf’s design, and the gorgeously studded white belt provides a disruptive shock that keeps the colors from feeling muddy. This is such a brilliant fit. I’ve reverse image searched and I can’t find the wearer, which is driving me crazy—let me know if you know them!
I’ve never seen a hoodie basically used in place of a sweater to freshen up what would otherwise, with no other changes, feel like a pretty boring, trendy look. The matching headband and turtleneck collar function like the Whoopi headphones above.
The military elements of a beret and felt jacket are feminized with the addition of cute little brooches—considering everyone is freaking out over the subtle encroachment of the military sphere over the fashion sphere, it’s nice to know how to diffuse the look with a few cutesy little flowers.
Cozy
I’m not here to be the 1000th person to recommend a cable-knit fisherman’s sweater to you this season, though I think something about wearing a luxurious knit with crappy sweats makes it a good look, probably has something to do with the fact that it seems like the devil-may-care combo of a recent divorcee (nubby socks that match the sweats complete the look, to be worn with slippers, clogs, or slides):
Anyway, I’m interested in Sally’s choice of red, a color that has for the past few years become relegated to a “pop”: tights or socks, perhaps a lip stain, but hardly ever the main event of an outfit. Whoopi in red satin striped PJs with mismatched accouterments makes a case for red outside the Santa Claus context:
I’m fascinated by the slippers, too—why are they facing the leg? Have you ever seen that before? If there are faces on slippers, they’re always facing out, right?
This cozy outfit feels like what Sally would wear if she were 40% less fastidious, modeled by the beautiful Shelley Duvall (RIP queen). I can’t figure out what the sheeny yarn used to knit the sweater is called, it’s almost velveteen—I used to have a sweater in this fabric and it’s excellent. Doesn’t pick up stains as easily as normal yarn and remains super hardy even after machine washing. Paired with the burnt-out velvet-looking pants (velvet is the most underrated fabric of the F/W season and I am waiting for it to receive justice) and a little jewel-studded velvet sack, this is the most insouciant red carpet look I have ever seen. She is the red carpet. And look at those pearls sneaking out from under her jauntily-rolled collar! This outfit demands the messiest bun of all time or 90s Drew Barrymore-esque bed head:
Contemporary Example
This 2017 look from Junya Watanabe’s Undercover deploys almost all the facets of Shelley’s fit—the loose cut, the patterned velvet, the pearls—but does it in a slightly punk, slightly creepy way, like a beekeeper in a dream.
Athleisure
Harry’s most casual looks are all comprised of athletic gear, from a Yankees crew neck sweatshirt to a Henley worn over Nike leggings that give him the best case of chicken legs I ever did see. Note an essential component of the latter outfit: the leggings are TUCKED IN to his socks. This is important.
I love Whoopi’s look here and though he’s more of a Giants fan, I think Harry would wear a sick Yankees jersey like this rare vintage brown one over a cream thermal long sleeve:
I wrote about shants/shorts over pants over two years ago and have seen them pop up in the coolest of the alt dressing circles multiple times since. Harry would sport the pairing for sheer practical reasons—getting twice as much wear out of his short shorts and keeping his tuchus warm—and he’d layer a low-cut tank top over a crew neck as seen above for the same reasons. Aviators are the most Harry sunglasses (if he bothered to wear them). Harry would go for a more muted color palette, but the crimson and gold takes this above an beyond his gloomy cold-weather grays.
Another outfit Harry would wear in a fever dream—he’d like the almost-hideous pattern, ankle-cropped and cinched hemline, and streamlined sneakers.
I almost thought this was Carrie Fisher, which would have been so appropriate for this post, but whoever it is looks cool as hell even in a basic black ensemble for three reasons: the light silver zipper breaks up the dark swath of nylon, the pert collar zipped all the way to the neck looks sleek enough to wear to a dinner or party, and the pops of cobalt and lime green from the cap and laces wake the whole thing up.
This is what Harry thought he looked like in that speedwalking outfit. I do wish SJP’s crew neck had that V stitch in front, which actually serves a purpose but mostly just makes a sweater look more sporty and less TikTok Shop Athleisure, but the intense heathering nearly makes up for it by giving the sweatshirt texture and staticky appeal. I also like that the leggings seem almost shiny and wish the socks were pulled up over their hems more.
Contemporary Examples
This is a very different take on the Athleisure above, but it still feels connected to Ephron’s ‘80s with its layers of cobalt nylon and striped shirt tied around the waist.
Finally, how Harry would go out prancing in 2025. The Velcro high tops add to the shape of the sweats stuffed into the socks, like twin vases that hold the bonsai of your body. I’m so into pants stuffed into socks right now, I don’t know what is up with me.
Here is the Pinterest board with all the photos above and their sources, plus many more. Sorry I didn’t go through and cite each photo individually, but unfortunately this is not my job and these posts already take me a million years now that I have an awful Chromebook. You don’t even want to know what my process for making the collages at the top of each post is. Anyway, thank you for being here, and I promise we will make it through the colder months together.
<3 ESK
Shelly’s sweater looks like chenille!
Is that possibly Madonna out jogging in that picture? Great article!!!!