When it comes to timeless beauty and undeniable presence, our Fall/Winter 2025 cover star Monica has always delivered. The multi-platinum singer has never missed a beat when it comes to rocking sleek ‘90s hairstyles and glossy lips. Every era has given us a new look to love—and just like her music, her beauty moments remain iconic.
Back in 1998, she was already giving us queen energy on the American Music Awards red carpet with light purple shimmery eyeshadow, winged eyeliner, and a deep pink lip that set the tone for her bold, glamorous style. By 1999, she kept the momentum going at the 13th Annual Soul Train Music Awards press conference with a sleek high ponytail, bold eyeliner, and glossy lips, exuding elegance and international star power. That same year, at the Kid’s Choice Awards, she switched it up with a striking red lip—proving she could make even a playful carpet moment iconic.
In 2000, she turned heads at the GRAMMY Awards in a short cropped cut reminiscent of Halle Berry in Monster’s Ball, paired with her go-to red lipstick, cementing her status as a beauty risk-taker. By 2010, at the Down to Earth Los Angeles premiere, Monica kept things understated but powerful, pulling her waves back into a ponytail and letting a classic winged liner and red lipstick do all the talking. Seven years later, she reinvented her pixie cut moment with blonde hair, copper eyeshadow, and pink lipstick—a look that felt modern and fearless.
In 2019, she doubled down on her beauty icon status, first at Black Girls Rock! with slicked-back hair and dramatic winged eyeliner, then at Black Women OWN the Conversation at Piedmont Park, where she gave us another twist on the pixie, pairing it with pink-and-black liner for an unexpected edge. This year, at the 2025 Breezy Bowl XX Official Tour After Party, Monica was radiant in long, parted hair with dark pink lipstick and eyeshadow.
Most recently? She graced our Fall/Winter cover, alongside Brandy, in a middle part buss down, a smoky eye, and a mauve lip—perfect for the autumnal season. All-in-all, she continues to prove that nearly three decades into her career, her beauty evolution remains just as iconic as her voice.
In honor of the legend gracing our Fall/Winter cover, here are our favorite beauty moments below.
Monica (Photo by Jim Smeal/Ron Galella Collection via Getty Images)
Monica during “Down To Earth” Los Angeles Premiere at Chinese Theatre in Hollywood, California, United States. (Photo by J. P. Aussenard/WireImage)
Monica during The 13th Annual Soul Train Music Awards – Press Conference at Hotel Nikko in Los Angeles, California, United States. (Photo by SGranitz/WireImage)
Monica during The 13th Annual Soul Train Music Awards at Shrine Auditorium in Los Angeles, California, United States. (Photo by SGranitz/WireImage)
Monica during 16th Annual Essence Awards at The Kodak Theatre in Hollywood, California, United States. (Photo by Jon Kopaloff/FilmMagic)
Monica during AMA ’98 in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Monica during 1999 Kid’s Choice Awards in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Monica at the 1998 Lady of Soul awards in Los Angeles. (Photo by Jeff Kravitz/FilmMagic, Inc)
Monica during Lilith Fair press conference – 1999 at Irving Plaza in New York City, New York, United States. (Photo by Steve Eichner/WireImage)
Monica during 23rd Annual American Music Awards at Shrine Auditorium in Los Angeles, California, United States. (Photo by Jim Smeal/Ron Galella Collection via Getty Images)
Monica during The 12th Annual Soul Train Music Awards at Shrine Auditorium in Los Angeles, California, United States. (Photo by Jim Smeal/Ron Galella Collection via Getty Images)
Monica during Monica on CBS “Early Show” for VH1 Save the Music – June 13, 2003 at CBS Early Show Studio in New York, New York, United States. (Photo by Marc Bryan-Brown/WireImage)
LOS ANGELES, CA – JULY 01: Recording artist Monica attends the BET Awards ’12 at The Shrine Auditorium on July 1, 2012 in Los Angeles, California. (Photo by Frederick M. Brown/Getty Images)
Monica during 2000 GRAMMY Awards at Staples Center in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
LOS ANGELES – 1998: Singer MONICA poses for a portrait in 1998 in Los Angeles, California. (Photo by Harry Langdon/Getty Images)
LOS ANGELES, CA – JUNE 28: Singer Monica attends the 2015 BET Awards on June 28, 2015 in Los Angeles, California. (Photo by Vincent Sandoval/WireImage)
NEW YORK, NY – JUNE 26: Recording artist Monica attends the 2017 NBA Awards at Basketball City – Pier 36 – South Street on June 26, 2017 in New York City. (Photo by Gonzalo Marroquin/Patrick McMullan via Getty Images)
ATLANTA, GA – JANUARY 14: Singer Monica attends Toya Wright’s Baby Shower at Test Kitchen on January 14, 2018 in Atlanta, Georgia.(Photo by Prince Williams/Getty Images)
NEWARK, NJ – AUGUST 25: Singer Monica attends 2019 Black Girls Rock! at NJ Performing Arts Center on August 25, 2019 in Newark, New Jersey. (Photo by Gilbert Carrasquillo/Getty Images)
ATLANTA, GEORGIA – AUGUST 06: Singer Monica poses backstage during the Black Women OWN the Conversation at Piedmont Park Greystone on August 06, 2019 in Atlanta, Georgia. (Photo by Paras Griffin/Getty Images)
ATLANTA, GEORGIA – AUGUST 30: Monica attends Breezy Bowl XX Official Tour After at The Dome Atlanta on August 30, 2025 in Atlanta, Georgia. (Photo by Prince Williams/WireImage)
