Even before the Confessions II film was debuted this week, we got a first glimpse of Madonna’s style era when she did a surprise Times Square performance in collaboration with Grindr last week. “We started by looking at what she has, what she’s worn, and what she hasn’t,” says Melssen. For the performance, the singer wore her silver Frida Giannini-era Gucci jacket from the first Confessions album, and paired it with custom Dolce corsetry, Swarovski jewelry, vintage Dior sunglasses (from Pechuga Vintage), and silver Saint Laurent boots from Madonna’s own archive. “Those YSL boots have been tried and true for her for a really long time,” says Melssen. “She’s very organized, and those pieces are very important to her. It’s not just clothing—they’re part of her history, and it has defined moments in her career.”
In the short film, Melssen delivered even more pop royalty-worthy looks. Each of the six songs has a distinct fashion feeling to it, and the ensembles were all brought to life by Dolce & Gabbana (some pieces custom-made, others pulled from their or Madonna’s personal archive). “We really looked at it as a film, and understanding what her character would be,” says Melssen. “Each scene had its own distinct style and feeling that was reflected also in the clothes.”
For her track “Good for the Soul,” for one, Madonna emerges in a misty landscape wearing a custom PVC dress by Dolce & Gabbana, with a vintage light pink shrug from Dolce spring 1998 thrown over the top. “It was from her own archive,” says Melssen. For “Danceteria,” she changes into a satiny light-blue Dolce club dress, with opera gloves to match. “It was a custom color to match her Ray of Light album cover,” says Melssen. “She was wearing Dolce on that cover, too, so it felt fun.” (Also fun? The cameos from Kate Moss, Gwendoline Christie, and Benedict Cumberbatch.)

