When Sweaters met Sally

Meg Ryan is one of my very favorite humans. When I watch Sally in When Harry Met Sally, I feel personally identified by Meg Ryan and her embodiment of this fabulously spunky, independent, tender, and wide-eyed woman who acts a whole lot like how I feel most of the time. It’s my favorite movie and I watch it more than a person should watch a single movie probably. Aka, a heck of a lot.

On a recent viewing (and, oh, there have been many) I paid particular attention to Sally’s wardrobe. Sally’s known for her stylish and just down-right-great wardrobe (despite the strange khaki short and knee socks incident in the first scene that’s weird but we all love her even more for it). Sweaters, leather gloves, great button-ups, all sorts of tweed, a truly fabulous hat. She’s just made it through a break-up, she has her own mostly pink apartment, and she looks darn good!! I watch the movie, I look at Sally, I feel her feels, I get her. And she looks pretty much just like how I want to look in the world. A lovely girl in lovely, sturdy clothes that all go together and outfit her for her life in her world. Sure, it’s all sort of 1989-ified, but the general style principles still hold. Dainty gold earrings, sturdy leather shoes, slim pants, great coats, gorgeous sweaters. Sally’s got style. All gorgeous and sensible clothing, lots of tweed and wool and leather. Sensible, practical. Sally exclaims it herself, “Women are very practical!” before making a passionate and hasty judgement of Ingrid Bergman’s decision at the end of Casablanca which she later takes back. In this moment she applauds Ilsa’s practicality in getting on the plane. Later, amazed at her earlier opinion, Sally decides Ilsa should have stayed with Rick. Of course she should have. But sweet stubborn 22-year-old Sally has to hold to her half-baked feminist ideas in front of Harry and all his confusing man brain aggression on the road trip from Hell, you know? But I digress.

Women are very practical and Sally certainly is, but she also knows how it feels to be inconsolably irrational, all spirally and sad. When she finds out that her ex is getting married, Sally pouts “I’m difficult,” weeps in her bathrobe all over Harry’s sweater, asks him to hold her a little longer, sleeps with him and feels so completely weird about it that it keeps her from feeling okay about hanging out with him for weeks, ignoring his charming voicemails, yelling at him at weddings, and not believing that he really is in love with her until he tells it to her straight to her face. This, friends, is where I completely identify with Sally, her confusion at her feelings, her shame for her actions that seemed like an okay/good thing at the time, her wanting to reconcile but feeling like she messed things up, her deep sadness and fear that she will never truly be matched by anyone, and her need to be told, truly told, what is good about her sometimes.

Sally is all sorts of woman, all the practical, all the lovely, and all the irrational. She is marvelously high maintenance because she knows what she wants. She is completely quirky without even trying. She is far lovelier than she even knows. She is feminine, sweet without sacrificing her smarts, and quick to laugh at all Harry’s jokes. And that is what’s so great about her. All those things rolled into a sweater-wearing woman who wants the dressing on side, smiles easily, is willing to get a giant Christmas tree just for herself, likes to browse bookstores, can’t carry a tune, takes tap dancing classes, and weeps when she sees her best friend’s wedding dress. Sally is wonderful.



I went ahead and made a truly obsessive list of every piece of clothing Sally wears in the film and how. I love her mixing and matching, her obvious rewearing of favorite pieces. She is sort of living the capsule life, in a way! Yes, of course, it is a movie, but I applaud the costume designer, Gloria Gresham, for making Sally feel like a real woman wearing real clothes.

This list moves chronologically, and I’m not making clear indications of what scene each outfit is attached to except for some little hints sometimes, so if you’re a fan of the film you can try to remember what scene is happening based on the outfit! SUCH NERD FUN! And if you’re not a fan of the film, BECOME ONE!

Also, if there is an article of clothing that doesn’t appear in one of the outfits, like pants, it’s because they never pan the camera down far enough to see them. I’m jazzed up by the idea of Sally’s mystery pants. MYSTERY PANTS!!!!!!!!

I’m also including some of my favorite quotes from the film attached to the outfits, just for fun. Passion projects, you guys. It’s important.

  1. Navy cardigan, yellow button up, little leather watch, little gold earrings, leather belt, leather shoulder bag, weird khaki shorts, navy knee socks, leather oxfords.
  2. Tweed blazer, white button up, red tie, little gold earrings, leather watch.
  3. Tweed jacket with big buttons all buttoned up, pearls, little gold hoops, silver watch. MYSTERY PANTS.
  4. Brown blazer, slim blue jeans, thick knit red turtleneck (truly fabulous), wire-rimmed glasses, “someone is staring at you in personal growth,” little gold hoop earrings, black leather bag, leather shoes, black leather watch, leather belt.
  5. Wire glasses, black cardigan with big brown buttons, white shirt, cool gold pin on cardigan, red shirt also layered under somehow (confusing wardrobe magic/maybe a goof up?)
  6. Pink leotard, white oversized button-up, black skirt, black tights, tap shoes, too good. (The most eighties outfit in the film, hands-down).
  7. Black blazer, black leather watch, white sweater with a sort of cowl neck (??? or maybe made of silk. Unsure), wire glasses, crazy arm gestures, classic Sally.
  8. Wide black pants, black leather shoes, black cross body bag, grey short jacket.
  9. Pajamas with a little pink pattern.
  10. Grey short jacket, black leather gloves, brown pants, leather shoes, GREAT BROWN HAT, brown sweater with red flecks and white spots, black leather bag, “I think you should wear skirts more. You look really good in skirts.”
  11. Red turtleneck, black skirt, black tights, gold earrings, little black flats.
  12. Grey v-neck sweater, white shirt with weird grey design and two buttons on top, fake orgasm and no one’s mad, pearl earrings, black pants.
  13. Fantastic grey wool coat (seriously, want it), black scarf, brown gloves, black bag, grey-brown pants, brown leather shoes/boots (??? unsure)
  14. Black heels, black tights, fantastic ruffly off-the-shoulder black party dress, fun dangly earrings, “see? now we can dance cheek to cheek.”
  15. Brown trench coat, white silk shirt, little black bag, black cardigan with deep v-neck, cool silver stud earrings, silver watch.
  16. White turtleneck, black bag, high-waisted blue jeans, leather belt, brown leather loafers with white socks, and a house-plant.
  17. Pink dress with scalloped neckline AND POCKETS, dainty gold necklace, gold bracelet, “he’s too tall to talk to”
  18. Pink fuzzy robe, white socks, nothing else???
  19. White silk shirt with weird neck, black pants.
  20. Grey blazer, white button up, leather belt, black shorts, black tights, gold earrings, “oh marie.”
  21. Green bridesmaids dress, cool gold necklace, matching gold earrings, matching bracelet, “I am the dog?” black tights, black heels.
  22. Great hat, khaki coat (also want), brown leather gloves, skinny blue jeans, big-ass Christmas tree, brown boots, black leather bag
  23. Wire glasses, purple turtleneck, blue jeans, leather belt
  24. Grey tweed button up jacket, black pants, brown trench coat, black bag.
  25. Pretty necklace, blue strapless party dress with weird arm bands, “anyway, it’s about old friends”
  26. Cool white wrap shirt, black pants, happily ever after.


And now, QUIZ!!! See if you can match the picture to the outfit! Isn’t this fun????? I’m having fun, at least.


B.Meg Ryan 2






ANSWERS: A-11, B-17, C-4, D-22, E-26, F-13


And, finally, SHOP SALLY. Some links to some very Sally clothes available on the internet! A modern take, to be sure, but great basics that Sally would be proud of. Clothes are meant to be worn and reworn, mixed and matched. Take a page from Sally and rock some classics to be worn over and over again.


Chunky turtleneck

Wool Blazer

Wool Coat

Brown hat

White button up

Black leather bucket bag


2 thoughts on “When Sweaters met Sally

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