Only days after her wedding to Blake Fielder-Civil in Miami, Florida on 18 May, 2007, Winehouse wore the gingham dress to film the music video for Tears Dry On Their Own, the fourth single released from her critically acclaimed second studio album Back To Black. The video, directed by David La Chapelle and filmed in Los Angeles on 22 May 2007, features Winehouse making her way through Echo Park and includes scenes filmed in a dim hotel room, the Grand Motel at 1479 S La Cienega Blvd. Tears Dry On Their Own was the penultimate music video Winehouse filmed before her untimely death on 23 July 2011. In the month following her death, Back To Black became the biggest selling album in the UK in the 21st Century.
Two days later, Winehouse wore the dress to the 2007 Ivor Novello awards in London, where she accepted the Best Contemporary Song award for Rehab. Tiptoe-ing up to the microphone, she said Thank you all very much, I didn't even have time to get drunk, I've only been here about 15 minutes. Over the course of her short career Winehouse won three Ivor Novello Awards and was the first artist in the history of the awards to be nominated for two awards in the same category.
Four days later Winehouse wore the dress on stage at her much anticipated homecoming concert at Shepherds Bush Empire. Originally billed for 2 February, the concert had been postponed twice due to 'unforeseen circumstances,' the latter postponement reportedly due to Winehouse falling and breaking her tooth. When the concert finally went ahead on 28 May, Winehouse was over thirty minutes late, yet despite mumbling between numbers and barely moving except to shimmy on the spot, she wowed the crowd with her vocal performance. The concert was filmed and released on DVD in November, 2007. The dress features on the cover of the DVD I Told You I Was Trouble: Amy Winehouse, Live in London.
The dress was originally donated by Winehouse to the online charity auction Celebrity Trash, organised by Diesel in 2008, with all proceeds donated to The Livity Trust.