I heard Meg Ryan describe Sleepless in Seattle as ‘a story about love in the movies’ and I thought that was perfect. From the references to An Affair to Remember and the classically inspired love-at-first-sight narrative, it’s definitely a timeless film and one of my favorite romcoms! If you’re new here, I’ve been rewatching some of our favorite romantic comedies and recreating the outfits from the lead characters. Scroll to the bottom of this post to see others in this series including Lucy from While You Were Sleeping, Kathleen Kelly from You’ve Got Mail, and Isabel from Stepmom.
Sleepless in Seattle was a fun one to rewatch because I spotted several locations I recognized from our time in Seattle, including Pike Place Market, the Space Needle, and Alki Beach (which was very close to where we lived and where we spent many a summer afternoon!) One time even, when we were close by, we sighted the houseboat where Sam and Jonah lived!
I got several requests to recreate Annie’s looks from this movie, and I can see why. Her style is very classic and simple with nods to the ‘80s and ‘90s with those big shoulders, pencil skirts, and long waists. I did take a few creative liberties with her looks for this post - I don’t think they even sell some of the styles she wore in this film anymore (ahem, giant shoulder pads). I kept the spirit of the look in tact though, don’t fret.
And because style goes beyond clothing, I wanted to draw your attention to the different braids Meg Ryan wears throughout the film which definitely contribute to the overall romantic feel of her looks. I took the time to look up a quick tutorial if you want to go for it (and I think you should!)
Recreating Annie Reed’s Looks from Sleepless in Seattle
Look One: Christmas Dinner
This is the holiday look Annie wears to her family’s Christmas party to which she brings her fiancé, Walter, an allergy ridden sensitive type but all around good guy. Her doubts about her engagement start creeping in when she is trying on her mother’s wedding dress. She’s also wearing this in the car on the way to Walter’s family’s house when she hears a radio show interviewing a widower named Sam who lives in Seattle.
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Look Two: At The Office
In this scene, we meet her coworker and friend, Becky, played by Rosie O’Donnell (talk about perfect casting!) where they are discussing the aforementioned radio show. For the office, she’s wearing a white blouse (I swapped in one with a tie at the neck), gray blazer (hers is very long - I updated it to be shorter) and a gray skirt.
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Look Three: At Her Brother’s Office
"Annie, when you're attracted to someone, it just means that your subconscious is attracted to their subconscious, subconsciously.”
In this scene, Annie shares her doubts with her brother Dennis. I would absolutely wear this outfit today, right now. She’s got on a gray cashmere sweater set, brown pleated trousers, and brown Mary Jane flats which you can’t see here. Everything she wears in the film has this timeless fit that’s relaxed but not too oversized.
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Look Four: Watching An Affair To Remember
In this scene, Annie is taking a walk after watching An Affair To Remember and reflecting on her relationship. This is her movie watching outfit! She wears a cream colored sweatshirt paired with blue joggers and then puts on a red zip up hoodie and canvas sneakers for a walk. Love this!
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Look Five: Airport Look
Besides the fact that this outfit is incredibly chic for airplane travel, this look is significant because Annie and Sam first see each other in this scene. I’ve recreated this outfit with a polo sweater, cream colored trousers (she’s actually wearing a knee length skirt) and white oxfords.
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Look Six: Second Meeting at the Houseboat
This look is iconic. It might be the one you think of the most when you think about this movie, probably because of that blue blazer which has massive shoulder pads, ha! She’s also wearing this fabulous trench coat which was very difficult to find a duplicate for but I tried and linked several options below.
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Look Seven: Comfy at the Hotel in Seattle
Here is another loungewear look Annie wears while chatting with her friend Becky about meeting Sam. Chic but cozy.
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Look Eight: Meeting at the Empire State Building
This scene lives in romcom history books. If you don’t watch the entire movie, at least just watch this scene and swoon. The most notable pieces of this outfit are definitely the coat with the exaggerated lapels and the light blue scarf, both of which I attempted to find similar options. I’m not sure exactly what she’s wearing underneath but based on little snippets I saw, it looks like a black blazer and dark skirt.
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Other posts I’ve done in this series:
Dressing Like Your Favorite Movie Characters: Isabel Kelly
Dressing Like Your Favorite Romcom Characters: Sally Albright (and Harry Burns, too!)
Dressing Like Your Favorite Romcom Characters: Kathleen Kelly
Dressing Like Your Favorite Romcom Characters: Lucy Eleanor Moderatz
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