Welcome to my new series - how to dress like your favorite romcom characters! If you’re like me and use the excuse of dwindling evening sunlight in the fall to rewatch your favorite romcoms you’ve already seen fifty times, then this series is for you.
I’m starting with a character from a movie that tops my list of all time favorites - While You Were Sleeping. I’ve loved this movie for so long! In fact, it might be one of the reasons I felt drawn towards the city of Chicago (we moved here in the summer of 2025).
If you haven’t seen it - first off, what are you even doing with your life? - second, let me give you a quick recap. Lucy Eleanor Moderatz is a lonely CTA worker with no family (CTA is the Chicago Transit Authority, the ‘L’ train, fyi). She develops a crush on a CTA patron who frequently comes through her station, a handsome workaholic executive type named Peter. On Christmas Day, Peter is mugged, pushed onto the tracks, and saved by Lucy. After a miscommunication at the hospital, a nurse mistakenly introduces Lucy to Peter’s family as his fiancé, and, in all the excitement and with Peter being in a coma, is unable to correct the mistake. Lucy quickly becomes a part of this boisterous, close-knit family and eventually falls in love with Peter’s brother, Jack. Did you get all that?! It’s a romcom plotline at it’s finest!
Lucy’s style is pure ‘90s - big, slouchy sweaters, jeans, and sensible shoes. She wears little jewelry and makeup and is often throwing her up into a messy updo using a clip or scrunchie. When she does get dressed up, it’s typically a wool sweater paired with a skirt and what I’m assuming are some walkable boots.
I rewatched the movie for the express purpose of writing this post (I know, tough job). I recreated my favorite looks with some shoppable pieces, but this post is really meant to just inspire you. I’m already thinking about how to incorporate Lucy’s casual style into my winter wardrobe.
Is it weird to plan your outfit for trimming the tree? Because I’m thinking this is what I’ll be wearing for the occasion. Instead of a normal sweatshirt/sweatpants combo, swap the top for a cable knit sweater, and, boom, you’re in a romcom. Don’t forget the thick slouchy socks.
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Lucy dresses for warmth not for aesthetics. In almost every scene, she is wearing a wool sweater usually in gray or black, and it’s always super oversized with the sleeves draping right over her hands. She even pulls a little present out the sleeve of one them. I plan to size up in all my sweaters from here on out.
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Here, Lucy is in the hospital being questioned by Jack, Peter’s brother. She’s wearing her signature look - sweater, jeans, and boots. If you look closely, you can see she is also is wearing a watch which I like to think was her father’s.
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Here is another loungewear look - a blue oversized sweatshirt worn over a white tee, gray sweatpants, and those thick socks again. Notice how she has her hair pulled back into a perfectly messy bun with a scrunchie. Love!
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If Lucy isn’t wearing sweats or jeans, she’s got on a long maxi skirt and sweater. I could never tell what footwear she was wearing for these more dressy looks, but I like to think she's got on some sensible ankle boots under there - a kitten heel at most. Something that can hold up in the Chicago snow.
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This look would translate so well to present time and is easily copied - big black sweater, some straight leg denim, and lace up boots. She’s also wearing a white tee underneath which is, honestly, right on trend.
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Lastly, this is what Lucy wears on New Year’s Eve which is a little different than what we see today, ha. I was never able to conclude what she was actually wearing on her bottom half while watching the movie but, based on her other looks, I’m assuming it was some kind of long skirt like this.
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Read More:
RomCom Inspired Outfits For Spring
Nancy Meyer’s Aesthetic Outfits For Spring
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