NEW YORK, 8 December 1997
On 8 December 1997, Madonna attended the Costume Institute Benefit Gala, currently named the Met Gala, honoring Gianni Versace at the Metropolitan Museum of Art in New York City.
For the event, Madonna donned a Versace Spring/Summer 1998 Ready-to-Wear crystal beaded cut out silk evening dress and a pair of silver Dolce & Gabbana sandals from the Spring/Summer 1998 collection. The Met Gala is a fundraising benefit that serves as an opening celebration for the Costume Institute’s annual fashion exhibit. Following the event, the exhibition runs for several months. Each year the event has a theme, and includes a cocktail hour and a formal dinner. The theme for the December 1997-March 1998 exhibition was Gianni Versace. Originally, Madonna was meant to perform, but backed out due to scheduling problems.
LOS ANGELES, 18 January 1998
Giving off strong Pre-Raphaelite vibes, Madonna stunned at the 55th annual Golden Globe Awards in a Balenciaga Fall/Winter 1998 dress, which she accessorized with a vintage necklace from Martin Katz.
The show was held at the Beverly Hilton Hotel in Los Angeles, California on 18 January 1998.
At the ceremony, Madonna presented Jack Nicholson with the “Best Actor in a Motion Picture – Musical or Comedy” award for his work in As Good as It Gets (1997). She attended the event with friend Ingrid Casares, Andy Bird and manager Caresse Henry.
Costume designer Arianne Phillips, who styled Madonna for the occasion, shared the story behind the look in an Instagram post, ‘’After an introduction from Inez and Vinoodh, I met with the insanely talented French designer Nicolas Ghesquière in his studio in Paris after obsessing over his debut collection for Balenciaga. This dress reflected a perfect moment in time. Madonna was a new mother, and she had a new album called “Ray of Light”. Everything felt new and possible, and this look oozed effervescence and femininity with historical references that felt undeniably modern. Madonna was a beaming ray of light.’’
Madonna wore the same Nicolas Ghesquière design for Balenciaga in the April 1998 issue of Spin magazine. Paris’ Palais Galliera showcased the dress as part of its 1997 Fashion Big Bang exhibit in 2023.
MIAMI, 3-4 February 1998
Madonna attended a round of US press junkets to promote her album Ray of Light at Hotel Astor in Miami Beach, Florida between 3-4 February 1998.
For the electronic press kit interview, Madonna chose a blue velvet damask burnout silk ruffle trim top from Voyage.
Voyage was a London-based label, owned by the Mazzilli family. During its heyday, it was described as “the most pretentious shop in Britain”. Voyage opened on Fulham Road in 1991 and closed its doors in 2002. Until 1997, Voyage was open to the public like any normal shop, but since then, access had been restricted to members only. Membership was free, but you could only join if personally invited by its owners. Lacking membership cards, Madonna, Julia Roberts and Naomi Campbell were all, allegedly, turned away.
NEW YORK, 13 February 1998
A day before her special Roxy performance, on 13 February 1998, Madonna was photographed leaving her Harperly Hall apartment in a vintage Mark & Syrie carpet coat, Gucci Spring/Summer 1998 slingback pumps and carrying Prada‘s iconic re-nylon bag.
NEW YORK, 15 March 1998
Madonna and pal Rosie O’Donnell attended the premiere of Wide Awake (1998) at the Ziegfeld Theatre in New York on 13 March 1998. The film is a comedy drama, which stars O’Donnell as Sister Terry, a baseball loving nun.
At the premiere, wore her favourite Atelier Versace coat from the Fall/Winter 1996 collection, which she first wore at the Evita premeire in December 1996.
LOS ANGELES, 22 March 1998
On 22 March 1998, Madonna attended the Miramax pre-Oscar party alongside Ingrid Casares and Demi Moore at the Beverly Wilshire Hotel in Beverly Hills, California in a clear top by Prada and a Jean Paul Gaultier couture coat.
LOS ANGELES, 23 March 1998
Madonna walked the red carpet at the 70th annual Academy Awards in front of the Shrine Auditorium on 23 March 1998 clad in Olivier Theyskens, Jean Paul Gaultier and Dolce & Gabbana.
At the ceremony, Madonna introduced the performances of “Best Original Song” nominees How Do I Live, Miss Misery and My Heart Will Go On. Afterwards, Madonna presented James Horner and Will Jennings with the award for “Best Original Song”. After the show, she attended the Vanity Fair Oscar Party at Morton’s Restaurant in West Hollywood. Her brother, Christopher Ciccone was her date for the evening. Secretly, however, her real date, Andy Bird, was already waiting for her inside Morton’s.
When asked by journalists how she felt on the red carpet, Madonna replied, ”like a princess at a ball”. Her look for the evening, styled by Arianne Phillips, consisted of a black silk robe redingote, designed by Oliver Theyskens which featured a sweeping train adorned with chantilly lace; opening below the waist to reveal a dove-gray ball skirt of multi-layered tulle by Jean Paul Gaultier and Dolce & Gabbana shoes. From that moment on, Olivier Theyskens’ designs gained a considerable amount of recognition. In 1999, the ensemble sold at Christie’s for $79,500.
However, it was the mid-19th century diamond, sapphire and pearl necklace from the Fred Leighton Estate which was la pièce de résistance. The necklace was auctioned by Christie’s in 2007 and sold for a whopping $120,100. Originally, Madonna was going to wear Martin Katz jewellery, just like she did at the 1998 Golden Globes, “On the day of the Oscars her stylist called at 1 p.m. and asked, “Do you have any big diamonds?” I faxed her copies, but she called back and said there wasn’t enough time. The next day, however, the stylist did borrow some jewellery for Madonna to wear in an upcoming video.”, said Katz in an interview for Los Angeles magazine in June 1998.
LOS ANGELES, 4 April 1998
On 4 April 1998, Madonna attended the 11th annual Nickelodeon’s Kids’ Choice Awards at the UCLA Pauley Pavilion in Los Angeles, where she sported the Voyage cardigan from the Vanity Fair photoshoot she did in November 1997 and a pair of Dolce & Gabbana strappy wedges which she first wore at Elizabeth Taylor’s 65th birthday party in February 1997. The show was presented by friend Rosie O’Donnell and Madonna presented the ”Best Film” award to Titanic (1997).
NEW YORK, 2 May 1998
Madonna was photographed by the paparazzi near her Central Park West apartment in Harperly Hall on 2 May 1998 rocking the iconic Vivienne Tam Spring/Summer 1995 red and black Mao portrait print jacket.
NEW YORK, late spring 1998
On a hot late spring day, Madonna was photographed returning to her apartment at Harperly Hall after attending violin lessons wearing a pair of Vivienne Tam trousers from her Spring/Summer 1998 collection.
Madonna was taking violin lessions for a movie role she was preparing for, directed by Wes Craven, 50 Violins, which was supposed to start filming in August 1998.
The movie was based on the life of Roberta Guaspari-Tzavaras, a single mother who started teaching the violin in East Harlem schools to support her family. However, on 17 July 1998, Madonna and Wes Craven mutually agreed to part ways on the project. “Creative differences” were the cause of Madonna’s departure. She was said to have been unhappy with how little the movie had in common with the teacher’s real life. The film was renamed Music of the Heart and Meryl Streep was given Roberta’s role.
NEW YORK, 27 May 1998
Madonna hosted Ingrid Casares’ 34th birthday bash at the Kit Kat Club in Manhattan on 27 May 1998 in a sequin Vivienne Tam top and a custom Esteban Cortázar cowboy hat.
LONDON, late June 1998
Madonna flew out to London in late June 1998 to film the video for Ray of Light’s third single release, Drowned World / Substitute for Love. During her short visit, Madonna was photographed one evening in West London rocking red python trousers from Alexander McQueen‘s Fall/Winter 1998 collection titled Joan. Madonna first wore the trousers for a Rolling Stone photoshoot in May 1998.
NEW YORK, 13 July 1998
After her yoga class, Madonna was photographed by the paprazzi while heading home to Harperley Hall on 13 July 1998 carrying Prada‘s re-nylon bag.
NEW YORK, 25 August 1998
Clad in Anna Molinari for Blumarine, Madonna attended a press junket at the Blue Star Restaurant in Manhattan, New York on 25 August 1998, where she was interviewed for US, Australian, Spanish and Brazilian TV.
For the press junket, Madonna opted for a fur-trimmed cardigan and flower embellished dress, both from the Blumarine’s Fall/Winter 1998 collection, and wore Mehndi tattoos on her left hand as the Ebel photoshoot with Alek Keshishian was coming up.
NEW YORK, late-October 1998
Madonna was photographed out and about on the streets of Manhattan in late October 1998 wearing a Vivienne Tam Fall/Winter 1998 runway look. On that same day, Madonna taped a promo video for a Radio NRJ sweepstake, where fans were given the opportunity to interview her at the Hôtel de Crillon on 9 November 1998. In the video, Madonna can be seen sporting the same outfit.
STOCKHOLM, 14 November 1998
With ruby red painted lips and wearing porcelain-white make-up, Madonna made sure to showcase Hatsumomo’s influence on her sense of style at a press conference in Stockholm, Sweden at the Grand Hôtel. At the 14 November 1998 event, she sparkled in a red leather Gucci by Tom Ford jacket and a pair of red embellished trousers, both from the Spring/Summer 1999 collection. The look’s vibe was taken to the Far East with a pair of white tabi socks and Diavolina Los Angeles thong sandals.
LONDON, 20 November 1998
Madonna rewore the Kyoto-influenced attire from the Stockholm press conference for an interview with Johnny Vaughan in London, England on 20 November 1998.
MICHIGAN, 26 November 1998
On Thanksgiving 1998, Madonna went to Michigan and spent her holidays with her family and siblings. In a polaroid taken during the celebrations, which appeared in Christopher Ciccone’s book Life with My Sister Madonna, Madonna can be seen casually rocking a Blumarine Fall/Winter 1998 dress.
NEW YORK, 29 November 1998
On 29 November 1998, Madonna was photographed while leaving Cipriani Restaurant, after having dinner with Pras from The Fugees, wearing a pair of Gucci Spring/Summer 1999 embellished trousers.
Madonna was also carrying a Versace Spring/Summer 1999 hand painted brown and white pony hair tote bag. Madonna styled the look with a pair of white tabi socks and her favourite Diavolina Los Angeles sandals.
LOS ANGELES, 9 December 1998
At Donatella Versace’s Fire & Ice Ball at Universal Studios in Los Angeles on 9 December 1998, Madonna amazed in an Atelier Versace Fall/Winter 1998 zipper-gyration black leather evening gown. The event benefited the UCLA Women’s Cancer Research Program.
The dress was designed by Versace’s head of design for the couture line at the time, Jørgen Simonsen, who worked with Madonna on her costumes for the Max Factor ad campaign in early 1999.
MIAMI, 31 December 1998
Madonna celebrated New Year’s Eve 1999 in South Beach, Miami in a Blumarine Fall/Winter 1998 fur collar coat. This coat would later make a spectacular comeback during Madonna’s Confessions on a Dance Floor Promo Tour in late 2005.
NEW YORK, 18 January 1999
For her lengthy interview with Larry King at the CNN Studios at Time Warner Center on 18 January 1999, Madonna opted for a black leather Gucci by Tom Ford jacket and a pair of grey embellished trousers, also by Gucci.
NEW YORK, early February 1999
In early February 1999, Madonna sat down with Charlie Rose at her Harperly Hall apartment for an interviewfor CBS’ 60 Minutes. For the chat, Madonna sported a custom-made Versace crystal beaded tunic with blue silk lining and trouser tailleur inspired by the brand’s Fall/Winter 1999 Ready-to-Wear collection.
NEW YORK, 10 February 1999
Madonna donned an Atelier Versace Spring/Summer 1999 overlay while attending a reception commemorating the release of the March 1999 issue of Esquire magazine at the Astra in the D&D Building in New York on 10 February 1999.
The issue, which featured Madonna on the cover, was dedicated to calling attention to AIDS and Madonna made a brief speech, reminding people that the problem of AIDS and HIV remains very real. “There are people that think we’ve found the cure for AIDS and we can all sit back and relax and then there are people who just don’t give a damn. I’m here to say that anyone with a conscience has a responsibility to themselves and to the rest of humanity to not be lulled into this sort of complacency”, declared Madonna in her speech before introducing then-chair of AMFAR, Dr. Mathilde Krim.
LOS ANGELES, 16 February 1999
At the premiere of Guy Ritchie’s British crime comedy film Lock, Stock and Two Smoking Barrels (1998) at Sony Studios on 16 February 1999, Madonna showed up in a top from Alexander McQueen‘s memorable Spring/Summer 1999 collection, No. 13.
Madonna Outfits 