Happy birthday, Madonna! It’s hard to fathom that the mom of six turns 59 on August 16. And since she first broke out in 1982 with the hit Everybody, the beauty chameleon has played with just about every look under the sun. Her longtime makeup artist, Gina Brooke, tells Allure that in fact, Madonna isn’t particularly high-maintenance. It takes her “45 minutes” to get ready, and “hair and makeup is done at the same time, always.” So in honor of her big day, here’s a look back at some of the superstar’s most notable style moments.

1987 in Culver City
This has got to be one of our favorite, chill, relaxed Madonna looks ever. A simple high pony and a red lip to punch it up.
1985 in New York
This is peak, signature ’80s Madonna, performing at Live Aid. The hair and makeup is a bit gritty-glam here, with dark liner and red lips.
1985 in Chicago
Like a virgin? Yes please, as Madonna went full bridal while performing in Illinois. The singer pulled back her shaggy waves with that signature headband, and rocked the dark liner/red lips combo.
1989 in Los Angeles
Short hair? Do care. Madonna’s shaggy lob was on trend before lobs were even a thing.
1990 in New York
The singer was all smiles with her sleek hair at the MTV Video Music Awards. Dark, defined lashes and a flushed, moisturized lip gave off a polished but natural vibe.
1996 in Los Angeles
Madonna brought the thunder for the West Coast premiere of Evita. Berry lips, heavily-winged eyeliner and thin brows tied together the dramatic look, which also featured an elaborate updo topped off by an ornate, floral flourished hat.
1999 in Los Angeles
Madonna served sexy ringlets as #HairGoals at the Vanity Fair Oscar party.
2001 in London
This sleek, straight and blown-out look was the call for the singer during the Guy Ritchie years in the UK.
2005 in Tokyo
Madonna rocked a feathered ‘do during her Confessions on a Dance Floor era.
2010 in New York
At work while directing her film W.E., Madonna (naturally) went easy on the glam. “For every day she likes it very specific,” notes Brooke, saying the singer keeps things simple when she’s not on the red carpet.
2011 in New York
Madonna posed for her life at the premiere of her W.E. film. “I would say that she is very detailed” about how she looks, says Brooke. Her large, loose waves were the perfect pairing for this beauty look, completed with winged eyeliner and a nude lip.
2011 in Los Angeles
Madonna and her mini-me Lourdes looked so sweet together on the red carpet for the annual Vanity Fair Oscar party. When it comes to getting ready for major events, “She knows what she likes,” says Brooke. For this one? Stick-straight blonde strands, just enough eye makeup, and nude lips.
2012 in Miami
Madonna went for a full red lip and heavily lined eyes for this particular performance. Retro curls contributed to the bombshell beauty look she had going on from the neck up. But what goes on always comes off. “She’s always had good skin. She was born with great skin. She washes her face. She’s very regimented,” says Brooke.
2012 in New York
Madonna went for mussed and sexy at the launch of her fragrance. Loose curls, lashes, black eyeliner and again, a neutral lip was her pick for the occasion. The singer loves to collaborate on her makeup, but, says Brooke, “She’s extremely specific about how she wants to look.”
2012 in Hollywood
Madonna radiated that enviable inner glow at the Golden Globes, with side-parted hair cascading down in loose waves, and neutral, flattering makeup which let her skin take center stage.
2013 in London
We’re loving this understated look at the Chime for Change event in the UK. In her day-to-day life, says Brooke, “she doesn’t like (makeup) to be heavy. She’d curl her lashes, do mascara and lips and maybe concealer.”
2013 in Las Vegas
Madonna dished out legs for days and moody eyes at the Billboard awards. When it comes to her face, she’s very thorough about what’s going on it. “She’s very particular about products. She wants to know what the ingredients are and how it’s used,” says Brooke.
2013 in New York
We’re loving the chapeau, the scarlet lips and the mega-lashes at the Madonna: The MDNA Tour premiere in Manhattan.
2014 in Los Angeles
Mom and son David are a matched pair at the Grammys. The matte texture to her face really made her red lipstick shine here.
2015 in New York City
Another Met Ball, another of Madonna’s no-holds barred ensembles. This time, with long locks and a scarlet manicure.
2015 in Los Angeles
The heavily-lined eyes coupled with the rosy lips give Madonna that perfect red carpet dewiness at the Grammys. Plus, let’s get into that undo!
2016 in Atlanta
The flowing, wavy hair, coupled with the maroon lip made for a killer look on tour.

2017 in New York
Madonna brought full-on glamour to the Met Ball, with smoky eyes and a greyish nude lip, which paired nicely with the camo print on her gown.

Daring LOOKS Iconic COVER!

The cover star of October’s Harpers Bazaar “The Daring Issue, dress to thrill” Madonna’s stunning look captivates. The iconic cover and photos within were shot by photographer Terry Richardson, I created custom lashes for the shoot, along with the makeup. Click through to my Facebook for more photos! xxGina

Makeup and custom lashes created by me, Gina Brooke.

Makeup and custom lashes created by me, Gina Brooke.