Jane Nichols (Katherine Heigl) has been a bridesmaid for 27 weddings. One night when she is attending two weddings almost simultaneously, she meets Kevin Doyle (James Marsden), who helps her get home but discusses with her his cynical views of marriage. He finds her day planner in the cab they shared. Meanwhile, Jane's sister Tess (Malin Åkerman) arrives from Europe and falls in love with Jane's boss George (Edward Burns) at first sight. Tess pretends to like the same things that George does to get him to like her. Despite being in love with George herself, Jane does not reveal the truth and her sister's courtship progresses rapidly. Soon the new couple announce that they intend to marry in three weeks and Jane becomes the wedding planner.
The reporter who agrees to cover their wedding for the society page turns out to be Kevin, who writes wedding announcements under the pseudonym Malcolm Doyle. After looking at the contents of Jane's planner, he decides to use the contents as material for a piece on the "perennial bridesmaid" and hopefully be promoted to writing investigative pieces about "real" news.
Jane is unaware of Kevin's intentions. When he asks to interview her for his column on Tess, he gets her to try on all 27 bridesmaids dresses in her closet. He takes pictures of her in all of them and sends them with the completed article to his boss. As they get to know each other, Kevin begins to think that Jane is not as one-dimensional as he thought and asks his editor to hold his article so he can "fix" it.
When Kevin finds out that Jane is getting her sister's marriage fixed with the man she loves, he rebukes her. Jane agrees to one drink with Kevin and ends up getting drunk. Kevin and Jane kiss and have sex in the car. The next morning, the two go to a diner and a waitress recognizes Jane. Kevin's editor ran the article on the front page of the 'Commitments' section, despite Kevin and her settling to hold it for a while. When Jane finds out about it, she feels betrayed and is furious at him. Tess then gets angry at Jane for giving Kevin material about her, whom he describes as a bridezilla. The fight escalates when Jane sees that Tess altered their late mother's wedding dress to her own style — the last straw on Tess' string of lies to George and demands on Jane.
Despite the fight, Tess asks Jane to make a slideshow for her engagement party. Jane decides that George should know the truth about Tess and shows pictures of Tess with other men, eating ribs (as she claimed that she is a vegan, like George), holding a cat by the tail, and recoiling from George's dog (she told him that she loves dogs, but actually hates them) — in short, doing all the things she had told George that she never did. After that, Pedro, the child George mentors, tells the crowd that Tess had him clean George's apartment for money. George breaks off the engagement. Jane's friend points out that telling the truth to George and breaking their engagement didn't make her feel better. The next day, Jane confronts Tess to apologize. She is still mad with Jane, as Tess believes that Jane resented her throughout the years. Tess reveals that the reason she stayed in New York was because she got fired from her job and her boyfriend dumped her; she explains that when she met George she'd tried to be like Jane since she fell in love with him.
Later at work, George tells Jane that he appreciates her because she never says no. Remembering that Kevin once said the same thing as a criticism, Jane quits and admits she only stayed at the job because she was in love with George. She discovers after an experimental kiss that she no longer loves him and goes to meet Kevin. She announces in front of a crowd at a wedding he is covering that she is in love with him.
One year later Jane and Kevin are getting married. George and Tess meet again and a hope for a second chance shows. All 27 brides who Jane helped, as well as Tess and Casey (Judy Greer, her best friend), are her bridesmaids, wearing the dresses she once wore as their bridesmaid.Katherine Heigl as Jane Nichols
Peyton Roi List as Young Jane Nichols
James Marsden as Kevin Malcolm Doyle
Malin Åkerman as Tess Nichols
Charli Barcena as Young Tess Nichols
Edward Burns as George
Judy Greer as Casey
Melora Hardin as Maureen
Michael Ziegfeld as Khaleel
Brian Kerwin as Hal Nichols
Maulik Pancholy as Trent
David Castro as Pedro
Krysten Ritter as Gina
Principal photography began on May 10, 2007. The film was primarily shot in the state of Rhode Island. Locations included Rosecliff and Marble House mansions, a beach in Charlestown, East Greenwich, and Providence. Filming also took place during two weeks in New York City.
The film opened at #2 at the North American box office making USD 23 million in its opening weekend behind Cloverfield. As of April 18, 2009, 27 Dresses had grossed $76,808,654 in North America, and $83,450,665 overseas, for a total worldwide gross of $160,259,319.
According to BoxOfficeGuru.com, "The audience for the $30M-budgeted 27 Dresses was overwhelmingly female. Studio research showed that 75% of the crowd consisted of women, but the audience was evenly split between persons over and under 25."
27 Dresses received generally mixed reviews from critics. The review aggregator Rotten Tomatoes reported that 41% of critics gave the film positive reviews, based on 148 reviews with the comment being "The filmmakers perfectly follow the well-worn romantic comedy formula, rendering 27 Dresses clichéd and mostly forgettable." Metacritic reported the film had an average score of 47 out of 100, based on 31 reviews.
The Blu-ray Disc and DVD was released on April 29, 2008 in the United States and July 29 in the United Kingdom.
The movie features a score written by Randy Edelman along with numerous songs from other artists. These songs do not appear on the soundtrack CD, which includes only the Edelman score.