9 of the best outfits from 'When Harry Met Sally'

Erin McDowellJul 21, 2022, 19:32 IST

Billy Crystal and Meg Ryan in "When Harry Met Sally."Metro-Goldwyn-Mayer Studios Inc.

"When Harry Met Sally" premiered 33 years ago on July 21, 1989.
The romantic comedy has been lauded for its witty writing and iconic fall fashion moments.

The first outfit that Sally wears in the movie gives us insight into her character.

Meg Ryan in "When Harry Met Sally."Netflix

Sally is originally portrayed as an uptight girl who likes things a very certain way. She wears an outfit in keeping with collegiate fashion trends of the 1970s, including feathered hair, knee-high socks, and a cardigan over a pale yellow button-up shirt.

The next time we see Sally, she embodies 1980s fashion in a tweed blazer, white shirt, and red necktie.

Meg Ryan in "When Harry Met Sally."Netflix

The outfit is more polished and mature, perhaps due to the fact that she's no longer in college and is dating a high-powered lawyer.

When Harry and Sally reconnect at a book store, she wears a more casual look.

Meg Ryan in "When Harry Met Sally."Netflix

She pairs a brown structured blazer with a red turtleneck, glasses, jeans, and short boots.

In one of the most iconic outfits from the movie, Sally wears a brown velvet bowler hat, a floral printed shirt, pants, and a grey tweed blazer.

Meg Ryan in "When Harry Met Sally."Metro-Goldwyn-Mayer Studios Inc.

She pairs the look with a pair of black leather gloves and a matching messenger bag. After telling Harry she plans to wear the outfit on a date, he remarks, "you should wear skirts more, you look really good in skirts."

She pairs the look with a pair of black leather gloves and a matching messenger bag. After telling Harry she plans to wear the outfit on a date, he remarks, you should wear skirts more, you look really good in skirts.

At a New Year's Eve party, Sally wears a black off-the-shoulder dress with sheer tights and black kitten heels.

Meg Ryan in "When Harry Met Sally."Netflix

The dress features a ruffled skirt perfectly in keeping with 1980s fashion. According to Vogue, "the '80s were a boom time for shoulders of all varieties," from off-the-shoulder tops and dresses to shoulder pads and structured jackets.

The dress features a ruffled skirt perfectly in keeping with 1980s fashion. According to Vogue, the '80s were a boom time for shoulders of all varieties, from off-the-shoulder tops and dresses to shoulder pads and structured jackets.

Harry keeps his style simple and casual throughout the movie, often opting for button-ups and sweaters.

Billy Crystal in "When Harry Met Sally."Netflix

This white fisherman sweater is one of Harry's more dressed-up looks. He pairs it with a fitted pair of jeans and white sneakers.

Marie wears a sleeveless black turtleneck and grey pants when Harry and Sally come over to her and Jess's apartment.

Carrie Fisher in "When Harry Met Sally."Netflix

She pairs the casual look with gold jewelry and white sneakers.

At a dinner party, Sally wears her most colorful outfit from the movie.

Meg Ryan in "When Harry Met Sally."Netflix

Her pale pink dress features a scalloped neckline that shows off her perfectly crimped hair.

Sally's bridesmaid dress adds just the right amount of drama to the iconic scene in which she slaps Harry for saying that sleeping together didn't "mean everything."

Meg Ryan in "When Harry Met Sally."Netflix

The dress is floor-length and features swatches of dark emerald green and black, a sweetheart neckline, and puff sleeves.

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9 of the best outfits from 'When Harry Met Sally'

The first outfit that Sally wears in the movie gives us insight into her character.

The next time we see Sally, she embodies 1980s fashion in a tweed blazer, white shirt, and red necktie.

When Harry and Sally reconnect at a book store, she wears a more casual look.

In one of the most iconic outfits from the movie, Sally wears a brown velvet bowler hat, a floral printed shirt, pants, and a grey tweed blazer.

At a New Year's Eve party, Sally wears a black off-the-shoulder dress with sheer tights and black kitten heels.

Harry keeps his style simple and casual throughout the movie, often opting for button-ups and sweaters.

Marie wears a sleeveless black turtleneck and grey pants when Harry and Sally come over to her and Jess's apartment.

At a dinner party, Sally wears her most colorful outfit from the movie.

Sally's bridesmaid dress adds just the right amount of drama to the iconic scene in which she slaps Harry for saying that sleeping together didn't "mean everything."