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madge_glee_v031 of 23
The Hello2 of 23
By Abby Gardner
We were all introduced to this NYC-via-Detroit future Queen of Pop in the early ‘80s. She came to define the era with her stacked bangles, streaky highlights, and devil-may-care approach to just about everything.
The Virgin Bride3 of 23
Admit it, you totally made your mom buy some white lace gloves after Madonna's historic Video Music Awards performance. We sure did.
RELATED ON WONDERWALL: Fantasy Casting the Madonna Biopic
The Brows4 of 23
Most colorists wouldn’t let you walk out of the salon with hair this blonde and brows this dark; but what Madonna wants, Madonna gets. In 1987, she made natural eyebrows and platinum hair cool. We wouldn’t suggest trying a contrast this harsh.
The Conehead5 of 23
The Blonde Ambition tour was amazing on so many levels. Cone bra anyone? Jean Paul Gaultier’s designs defined those shows. Along with “Like A Prayer.” And that unforgettable ponytail.
The Marilyn6 of 23
When Madonna and Michael Jackson attended the Oscars together (in 1991), they knew it was going to be a major moment. Channeling her inner Marilyn Monroe in white, diamonds and fur, Madonna did not disappoint. The result? Glam, glam, glam.
The Little Bo Peep7 of 23
Let us just say that we love seeing fashion risks. But this German-Little-Bo-Peep-meets-Tokyo-teen look warrants some discussion, right? As in, “Wow, that’s some cleavage!”
The Fall Girl8 of 23
Thanks to some amazing fake tresses, Madge rocked a modern Brigitte Bardot look at the 1995 VMAs, along with one of the first visible bra moments on the red carpet. But what we also remember is that uncomfortable interaction with Courtney Love.
The Evita9 of 23
No one has probably ever cried for her but boy, did we love how Madonna went all-out Eva Peron for the premiere of the movie. The color, the velvet and the veil are especially fantastic.
The Super Sexy10 of 23
Madonna went sexpot at the 1997 Oscars in a simple (for her) Dolce & Gabbana black dress. Best accessories: that crimson lip and Carlos Leon (Lourdes’ dad).
The Free Spirit11 of 23
Who knew Madonna would have a grunge moment? But she did at the 1998 Golden Globes. We love the messy twists and braids. Now we can see where Mary-Kate and Ashley got their inspiration.
The Body Artist12 of 23
Would most of us have known about henna tattoos if Madonna hadn’t done this? Probably not. We’re happy we learned something new … but we never would have taken it this far.
The Natural13 of 23
The “Ray of Light” video highlights one of Madonna’s best-ever looks. Dark denim + subtle (and wearable) sparkly accessories + natural ringlets = perfection. The abs …we’re still working on.
The Geisha14 of 23
We love that Madonna embraces every culture. But it’s sure hard to keep up with her globe-trotting. This Asian-inspired moment at the Grammys in 1999 was one of her finer worldly moments.
The Cover-Up15 of 23
She might be better known for taking it off than covering it up, but wow did this tweed-trimmed Chanel trench on the red carpet make us all take notice.
The Outspoken16 of 23
A picture is worth a thousand words. But we don’t need more than one to know what was important to Madonna in 2004. Her clothes say it all: Guy Ritchie and Kabbalah. Discuss.
The Flip17 of 23
Madonna’s 2005 tour brought out her inner Farrah Fawcett in the form of a very sassy '70s-inspired feathered hairdo. We loved it and that blinged-out hair band.
The Redux18 of 23
Not many of us can pull off a version of an outfit we once wore 20 years ago — our bodies just haven’t aged that way. Well, Madonna can. Witness this leotard number from 2005 that is eerily reminiscent of her Blonde Ambition tour. Well done, M.
The Real Deal19 of 23
For someone as famous as she is, we don’t often see “off-duty” shots of Madonna. It’s too bad, because we’re fairly obsessed with her flared jeans, leopard-print bag and red leather jacket.
The Herbalist20 of 23
This Gucci party in 2009 was the event of the year in Manhattan. And, of course, Madonna wore the most discussion-worthy dress that made us think about, um, greener pastures. We’ll let you form your own opinions.
The Mad Hatter21 of 23
Madonna’s “Sticky and Sweet” tour wasn’t the first one where we saw her accessorize with a guitar, but the top hat? That was new. We’re still on the fence as to whether it worked to her style benefit.
The Hot Mama22 of 23
Lourdes is fast following in her famous mother’s footsteps as a fashion icon. And what a closet she has had to play dress-up in all these years. Color us very jealous.
The Now23 of 23
Yep, it’s official: Madonna’s done everything. We’ve loved watching her become the woman she is now, in style and life. This shot of her with adopted daughter Mercy sums up much of what we admire about her: She’s chic, charming and charitable.