One of the many, many things to love about rom-coms is the fact that they are so unapologetically aspirational in such a specific way. When we watch romantic comedies, everything is curated so perfectly, almost scientifically, to make us feel like this could also be our lives. From the perfect brownstone on the Upper West Side of Manhattan to the best friend who appears to exist solely for our benefit and jobs that are accidentally glamorous, there is a little something for everyone. And then, there are the dresses.
Much like Cinderella in the classic fairy tale, come down to That Dress. Sure, the everyday clothing in rom-coms tends to be attainably aspirational, but That Dress is special. It usually marks a change in our heroine’s storyline. A new beginning or a coming into her own. That Dress is the one so many of us secretly think about when we are going out for a big occasion of our own. And if slipping into That Dress could also include an iconic movie montage as some of our choices do, we’d be all the better for it.
As you get ready for wedding/garden party/vacation season, here’s a look back at some of the most iconic dresses from rom-coms.
Kate Hudson’s pale yellow silk dress in How To Lose A Guy In 10 Days
The year was 2003. Kate Hudson and Matthew McConaughey starred as journalist Andie Anderson and marketing executive Benjamin Barry in How To Lose A Guy In 10 Days. They meet, they accidentally fall in love, and then there’s a party where all of their machinations are about to come to light. But who cares, because Kate Hudson’s pale yellow silk dress is the absolute star of that party. And the movie, And pretty much every prom night since. This dress, with it’s low back and simple lines, has never gone out of style.
Sandra Bullock’s mini bodycon dress in Miss Congeniality
Not every iconic dress on this list is a gown, but every one of them is highly covetable. Like Sandra Bullock’s bodycon purple dress in 2000’s Miss Congeniality. When Bullock’s character, FBI agent Gracie Hart, walks out of her makeover à la Michael Caine in her strapless purple dress looking like a million bucks, everyone wanted it. And wanted that moment. And wanted Michael Caine to give us a makeover.
Angela Bassett’s hot pink maxi skirt and matching bikini top in How Stella Got Her Groove Back
Oh, to be Stella getting her groove back. If you’ve never seen Angela Bassett play Stella Payne in the 1998 movie How Stella Got Her Groove Back, you’re missing out on one of the best looks on this list. To watch Stella go from being an uptight stockbroker to meeting younger man Taye Diggs on a holiday in Montego Bay and transform her wardrobe with this hot pink maxi skirt and matching bikini top. A true ode to Stella embracing her power and also Angela Bassett’s incredible arms.
Julia Roberts’ lavender bridesmaid’s dress in My Best Friend’s Wedding
It might be tough to believe, but Julia Roberts actually made a big comeback when she starred in 1997’s My Best Friend’s Wedding. We hadn’t seen her in rom-coms for a minute, and it was so refreshing to see her big smile and her curls as she joyfully tried to stop her best friend (Dermot Mulroney) from marrying the love of his life (Cameron Diaz).
While Roberts’ character Jules spends much of the movie in jeans and loose blazers, which we also love, her truly perfect lavender bridesmaid’s dress has stayed with us. The neckline, the halter, the silk and crystals. This dress has convinced many a bridesmaid that their dress can be fabulous. Whether that’s true or not remains to be seen.
Jennifer Garner’s multicolored swing dress in 13 Going On 30
OK full disclosure, this dress from 2003’s 13 Going On 30 leans heavily into potential cute Halloween outfit territory. Thanks in no small part to the fact that Jenna Rink (Jennifer Garner) did the full “Thriller” dance in the dress. But this short, swingy, multicolored Versace dress hits a real sentimental note. As Jenna is meant to be a 13-year-old in the body of a 30-year-old woman, it really does look like we would have chosen for ourselves as teenagers. Plus, as she points out to a friend in the elevator before the party, she had “these incredible boobs to fill it out.”
Reese Witherspoon’s hot pink courtroom dress in Legally Blonde
Reese Witherspoon had a veritable closet full of amazing hot pink outfits as law student Elle Woods in the 2001 rom-com Legally Blonde. Dresses, skirts, bikinis, even a pale pink bunny suit for Halloween. But the soft fuscia shirtdress Elle wore when she finally found her footing in the courtroom is our favorite. Because it represented a big moment for Elle. She became her own version of herself in the courtroom. Wearing a true pink shirtdress with some sequined details, cuffs, and a great collar. We would still wear this dress now if we could.
Jennifer Lopez’s strapless gown in Maid In Manhattan
There are some things that don’t really hold up from the Like the stilted chemistry between Jennifer Lopez as hotel maid Marisa and Ralph Fiennes as political golden boy Christopher, for instance. But still, we will never get over her incredible dress. A gauzy, strapless gown in pale chiffon that Lopez wore to a literal ball with her hair in a chignon. Plus, the getting ready montage, where all of the people who cared about her pulled together to transform her, is worth a rewatch. As is the way Lopez’s dress moves in that movie. It’s magic.
Constance Wu’s ethereal baby blue dress in Crazy Rich Asians
The 2018 movie Crazy Rich Asians was full of absolutely stunning fashion. It was, after all, a movie about a hugely wealthy Chinese family hosting a wedding. Which you might think would make it difficult to choose just one incredible standout dress. Not at all. Constance Wu’s character Rachel had The Dress of the movie, an ethereal pastel blue Marchesa dress she wears during her triumphant return to her boyfriend Nick’s (Henry Golding) side at his friend’s wedding after being criticized by his mom (Michelle Yeoh). It was an incredible scene, and an incredible dress.
If you are looking for a showstopper of a dress for an event this summer, let these rom-com classics be your guide. If not for the exact style, but for the feelings they evoke. Romance, fun, and best of all, a true sense of self.