- Fridge Logic: Why wouldn't Jane have become a wedding planner, since she loves weddings so much?
- It's explained that Jane's job was only supposed to be a temporary job since she was fresh out of college and needed a job. However, she fell in love with George and kept the job to be near him.
- Heartwarming Moments: The titular twenty-seven dresses at Jane's wedding at the end, being worn by all the brides whose weddings she had worked so hard for.
- Hilarious in Hindsight: This is the one movie where James Marsden is not the Romantic False Lead.
- Hollywood Homely - And how! Katherine Heigl plays the "plain" sister... the same woman who plays a former underwear model on Grey's Anatomy.
- It's not so much that Jane is the "plain sister". It's that Tess is working as a model and Jane has been actively avoiding dating or presenting herself as a romantic prospect due to her years-long, hopeless infatuation with her boss. She and Kevin are both aware of her attractive appearance, but she's got no interest in exploitng it and he knows she's emotionally unavailable. Until they get hammered, throw caution (and clothes) to the wind, and do it in the car.
- Tear Jerker: Just that broken look on Jane's face when she learns Tess had their late mother's dress cut up. Jane loves and treasures every sentimental memento of their mother, and it's what causes her to finally snap and practically disown Tess as a sister.
YMMV / 27 Dresses