Why 27 Dresses Is the Ultimate Nostalgic Rom-Com

27 Dresses is a romantic comedy from 2008 that’s filled with humour, heartache, and... a lot of bridesmaid dresses. I will be breaking down the plot and characters of this classic in excruciating detail so buckle up. 

Firstly, I need to acknowledge my own bias. I absolutely love this movie. I was eleven when I first watched it and I was immediately obsessed. Although I didn’t understand a lot of the themes and the nuance of the film, the costumes and set design were so beautiful that I was taken with it. I loved the thought of getting to attend weddings all the time and even experimented with the idea of becoming a wedding planner thanks to this movie.

27 Dresses is a romantic comedy centred around Jane Nichols (played by Katherine Heigl), a woman who's been a bridesmaid 27 times but has never been a bride herself. The concept inspired by the often overlooked emotional journey of women who put others before themselves, often without prioritising their own needs and happiness.

The Plot:

Our story begins with a flashback scene of 1986, with a young Jane Nichols, who experiences a life-defining moment at her cousin's wedding. Eight-year-old Jane takes charge when the bride’s dress rips, using the ribbon from her sister's hair to make an impromptu fix. Jane is rewarded for this by being asked to carry the bride’s train as she walks down the aisle. This event marks Jane’s discovery of her ‘true calling’: being there for others on the most important day of their lives. From that point on, weddings become Jane’s passion and purpose.

Flash forward to present-day New York City. Adult Jane is in a bridal shop trying on a dress. The staff are cooing over her, telling her how beautiful she looks and she is basking in their praise. But don’t get the wrong idea—this isn’t her wedding. She’s simply the same size as the bride and is picking up the dress on her behalf. We quickly see that Jane has turned her childhood love of weddings into an unofficial side job.

During the ceremony, we see Jane continuously checking her watch and start to tap her foot nervously. After the formal part of the ceremony, she flees outside and that’s when the audience realise, that night she’s not just attending just one wedding—she’s attending two. With $300 paid upfront to a cab driver, Jane hops between two ceremonies, performing bridesmaid duties at both.

As Jane makes a mad dash to spend time at each of the weddings, she catches the eye of Kevin Doyle, a jaded journalist who witnesses Jane’s double act. Watching her throughout the night, Kevin quickly puts two and two together that Jane has been rushing between two separate weddings. They have a brief but memorable exchange where Kevin’s cynicism about weddings clashes with Jane’s enthusiasm. Unbeknownst to Jane, she accidentally leaves her prized wedding planning filofax in the cab. Kevin, curious about the life of a professional bridesmaid, skims through it, discovering an entire world of meticulous wedding plans that reveal Jane’s borderline obsession.

By day, Jane is an assistant to George, her handsome boss who runs some kind of eco business. Jane’s unrequited crush on George is no secret—she’s always available to help him, whether it’s organising his appointments or getting his morning coffee and breakfast. But George is blissfully unaware. Meanwhile, Kevin, who works at the New York Journal, is pushing to write a feature on the wedding industry, but his boss shuts him down. Until he pitches a new angle—an article about ‘the perpetual bridesmaid,’ based on Jane.

Things take a dramatic turn when Jane’s younger sister, Tess, arrives from Europe. Tess is the complete opposite of Jane—confident, beautiful, and effortlessly charming. Tess’s arrival complicates Jane’s life even further when they both attend a work party, and George, Jane’s George, is instantly smitten with Tess. Jane watches in heartache as her dream man is swept away by her own sister.

In a matter of weeks, Tess and George become an inseparable couple. Jane, as always, stays silent, putting her own feelings aside. Then comes the crushing blow—George proposes to Tess in front of Jane. Jane’s heartbreak is obvious, yet she agrees to be Tess’s maid of honour and take on the daunting task of planning the entire wedding in just three weeks.

Meanwhile, Kevin has been getting closer to Jane, partly for his story and partly because he’s genuinely fascinated by her. When Jane discovers his true identity—he’s Malcolm Doyle, the wedding columnist she’s admired for years—she feels utterly betrayed. Yet Kevin manages to worm his way back into Jane’s good graces, and they spend a night together, singing ‘Benny and the Jets’ on top of a bar and even sharing a kiss.

The next morning, Jane’s newfound happiness shatters when she discovers Kevin’s article about her—complete with photos of her in all 27 bridesmaid dresses—has hit the front page. She feels humiliated and betrayed, not just by Kevin but by the entire world that now sees her as a laughingstock. But instead of focusing on herself, Jane still prioritises Tess’s wedding, even as Tess continues to bulldoze over her feelings, including destroying their late mother’s wedding dress to suit her own tastes.

It all culminates at the engagement party, where Jane finally snaps. Instead of the supportive maid of honour speech she planned, Jane exposes Tess’s lies in a brutal slideshow, revealing unflattering photos and all the secrets Tess hid from George. The engagement is called off, and Tess is furious. Jane, having unleashed years of pent-up frustration, is left feeling alone.

Jane’s outburst, while destructive, becomes a catalyst for change. She quits her job, finally confronts her feelings for George, and begins to shed the ‘always-the-bridesmaid’ label that has defined her for so long. When she and Tess eventually reconcile, it’s clear that Jane has found her voice.

One year later, Jane has turned her life around. She’s standing at the altar on a beautiful beach, marrying Kevin—the man who once mocked her love for weddings but ultimately came to appreciate her for who she is. In a touching final shot, we see Jane’s 27 former brides gracing the ceremony, each wearing the bridesmaid dress they made Jane wear. It’s a picture-perfect ending for a woman who spent so long making everyone else’s dreams come true.

Closing Thoughts:

As an eleven year old watching this movie, my motivations for liking it were pure. I liked the dresses, I was fascinated by weddings and many of the scenes made me laugh. But re-watching this as an adult, I really feel like 27 Dresses is more then just a romantic comedy. It’s a story about self-discovery, sisterhood, and finding your own happiness. Jane’s journey from a self-sacrificing bridesmaid to a bride standing up for herself is one that resonates with anyone who’s ever felt stuck in a role that didn’t let them shine.

The movie is far from perfect and even the romance between Kevin and Jane isn’t always great considering he essentially harasses her into seeing him only so he can write a expose on her. But, I enjoy this movie for the nostalgia. The costumes and sets in this movie are beautiful and I actually think the acting is perfect for this type of movie. It’s funny, charming and a little ridiculous but a great nostalgic watch.