Style Crush: When Harry Met Sally… (1989)

I am far from the first person to make a Sally Albright style post, but When Harry Met Sally… is such a great film that I’m not even sorry. Nora Ephron’s screenwriting is on-point and costume designer Gloria Gresham created a wardrobe that feels effortless and lived-in.

Gresham does a particularly good job of reusing garments—there are quality pieces that keep coming back over the film’s span of 12 years, and the continued wear feels believable.

There are absolutely some 80s nightmares of outfits (Marie and Jess’s wedding, I’m looking at you) but this film gets so much right that I’m willing to overlook them.

When Harry Met Sally… follows titular characters Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) over the course of twelve years. The pair meet in 1977 when they make the drive from Chicago to New York together and instantly hate each other; a series of chance encounters sees them progress from enemies to friends to lovers. I’m going to dig right in and talk about some of my favourite outfits from the film as they appear on-screen.

It’s 1977 and our protagonists are driving up to NYC from Chicago. They stop at a roadside diner and talk Casablanca, men named Sheldon and days of the week underwear (“They don’t make Sunday. Because of God.”).

Sally’s outfit is very Boy Scout meets pony girl, but I really enjoy the preppy-but-comfy balance being struck here. The shirt, cardigan, cuffed safari shorts and knee socks paired with Farrah Fawcett-style feathered hair? Adorable. Judging by other shots, she’s wearing shiny brown horse-bit loafers—the kind that have been inescapable for the last few years thanks to Alessandro Michele’s Gucci.

Harry’s outfit is pretty standard guy wear, save for the thick ringer tee and sideburns. I didn’t get a glimpse of his shoes, but it wouldn’t surprise me if he were wearing red or maroon Converse under that table. It’s just that kind of outfit.

Let’s skip forward a little to their third encounter, ten years later. After running into each other in a book shop, we learn that our leads have both come out of longterm relationships and are a little closer to being on the same page. You can see that in their outfits: they’re both wearing brown-toned blazers over solid coloured tops and straight-cut jeans. The hues are different but complementary.

Sally’s high-necked cable knit jumper is gorgeously textured. I wouldn’t normally mix red, brown and dark wash jeans, but it just works. Harry’s outfit is fantastic too; is that a chambray shirt? The tan belt helps to tie in the warm tones of his tweed blazer, and the blue and brown suit him well.

Another walk through a park, and this time their colours match each other perfectly! I get such Annie Hall (1977) vibes from Meg Ryan’s wardrobe in this film, but this outfit especially. The pleated trousers, shiny leather shoes and blazer are so evocative of menswear but feel soft and relaxed.

Harry is wearing a brown leather jacket over a sweater with grey and red tones that really complement Sally’s outfit: the grey pairs with her blazer, and the hint of red mirrors the hearts on her jumper. You can see those a little better below.

See how the red hearts are a similar shape and size to the red pattern on Harry’s sweater? That’s no accident. They also complement the red leaves in the background.

Love the hat. Love the striped blazer. A simple gold hoop earring seems to be her go-to.

I think you should wear skirts more. You look really good in skirts. 

Harry Burns, When Harry Met Sally (1989)

Harry says this in the scene immediately preceding this one. I see you, Ms Ephron.

We see the return of Sally’s red sweater from the bookstore scene, but now we can actually appreciate its design. The sleeves are loose and the main fabric looks to be moss stitch; can you see the little bumps? There’s just one cable down the front, which helps to keep things looking sleek. I’m dying to find a pattern for it. Paired with a smart A-line skirt, black tights and rounded black suede ballet flats, the silhouette here is super classic. Definitely a personal favourite.

Let’s give Harry credit where it’s due, too: his matching jumper is excellent. The cables and high neck echo Sally’s, but the overall look is more relaxed. It shows that they’re more alike than they are different.

I couldn’t write a style post without including the infamous Katz’s Deli scene. The clothing isn’t the focus here—that’s why it’s so neutral and understated—but it’s still fun to look at.

The embroidery and double button detail on Sally’s shirt placket add a little extra visual interest to a simple outfit. The embroidery reminds me of Trachten, traditional clothing from German-speaking countries: the shirts often have embellished plackets, designed to be worn with Lederhosen and under a jacket. Interestingly, the silhouette is kind of similar to the first diner scene, back when the two of them are newly-minted college graduates. There’s still a dark knit over a light button-up, but it’s much more relaxed. Sally’s more relaxed as a character.

We also have some more cable knit, this time in the form of an oversized v-neck. Harry is also wearing a sweater, but it’s a plaid crew neck over a turtleneck. Complementary, but not quite as matchy as previous outfits.

Sally is wearing marsala nail polish, which I’ve recently seen in Urban Outfitters. It’s a nice alternative to true red and muted enough for a wardrobe full of neutrals.

Christmastime, and the duo are buying a tree. The outerwear in this film is seriously top-notch; I suppose that’s par for the course in New York. We’ve seen a lot of Sally’s black leather messenger bag in previous scenes. While I’m not super into the design, it’s really functional and goes with everything.

Harry is wearing another leather jacket: it looks pretty similar to the one he wore for their walk in the park, with its slouchy fit and Peter Pan collar, but it’s black rather than brown.

See? Strong coat game all round. I miss Carrie Fisher so much.

Sally’s cream turtleneck, high-waisted jeans and loafers from the karaoke scene are so current. You can’t quite tell in this shot, but she’s wearing a glossy brown mock-croc belt with a round buckle. It’s the kind of piece that looks frumpy on its own but adds a really gorgeous touch to basic outfits. There’s a tiny peek of a gold and crocodile watch on her wrist to match.

Harry’s plaid motif is back again, and more blue, too. Blue is definitely Harry’s signature colour. His overall vibe is relaxed and slouchy, with plenty of straight lines. His belt and watch are almost matches for Sally’s, and Sally’s sweater reminds me a little of Harry’s cream cable knit earlier.

Major Dirty Dancing (1987) vibes from Sally’s party dress—the fitted bodice, scoop neckline and flared skirt combined with the soft pink colour feel like an intentional reference. She’s literally standing in front of the word ‘Baby’! The scalloping is a nice touch and linen is a great choice for Sally’s wardrobe: it drapes beautifully but lends a more casual feel than typical cocktail dress fabrics like satin and organza. It’s perfect for dinner and Pictionary at Marie and Jess’s.

I haven’t included a shot of what the others are wearing because I’m just not feeling the 80s baggy shirt vibe, but there are lots of creams and muted pinks and greens in this scene. Interestingly, none of the couples seem to match each other.

The menswear-inspired outfit she wears during Marie’s wedding dress shopping scene stands out in sharp relief to the shop’s frilly Rococo decor. It’s such a fun contrast—she’s slouching on this stiff pink sofa, eating peanut M&M’s instead of the prim-and-proper tea and biscuits provided. Can you imagine 1977 Sally doing that?

The pinstriped blazer from the park and museum scene returns, this time combined with dress shorts, diamond-patterned tights and a classic white shirt. It’s almost a throwback to her very first outfit with the shorts and knee socks, but grown-up. She’s also wearing a blouse we saw briefly in a workout scene during a montage.

I mentioned this earlier, but I really enjoy the reuse of garments in this film. It’s realistic, and it fits with Sally’s character: she’s a practical woman, she likes what she likes, but she’s not afraid to change things up. If you have a really nice staple blazer, why shouldn’t you wear it several ways?

I’m ending this post here for levity, but here‘s a fantastic list of every outfit Meg Ryan wears in the film. I adore the Oxfords and grey blazer with pleats she wears during the mailbox scene and really wish I had a sharp screencap of the outfit—it’s easily a personal favourite.

I plan to write a few posts like this exploring costume and style in my favourite films. You can find them under the tag ‘fashion in film’!

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