My All-Time Favorite Madonna Beauty Looks, Because I'm Seeing the Rebel Heart Tour Tonight!

Her skin is perfect and porcelain. Her body defies explanation. She’s unstoppable.
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Her skin is perfect and porcelain. Her body defies explanation. She’s unstoppable.

I’ve always loved Madonna. She’s never been my favorite pop star (hi, Britney!) but the thing is, Madonna is so much more than a pop star. 

The masses can say that she isn’t aging the way society thinks she should be aging, or she’s trying too hard to stay relevant, or whatever, but the fact is that Madonna is 57 years old and changed the pop music landscape—and popular culture—in a huge way, simply by being her strong, ballsy, talented self. In my personal opinion, she’s an icon.

I saw Madonna in concert during her MDNA phase, and while I knew I would be wowed, I wasn’t expecting to be as blown away by her sheer force and power as I was. It helps that I was about 12 feet from her, too. You know those “un-Photoshopped” photos of her that circulate around the internet every so often? She does not look like that at all. She looks absolutely insane. Her skin is perfect and porcelain. Her body defies explanation. She’s unstoppable. She dances like a maniac for two hours. I don’t know how she does it.

I’ll be seeing Madonna again tonight at the St. Paul stop of her Rebel Heart tour and I’m so excited. I even got my nails done in homage to a Madonna manicure of the past, and I’ve been reading old interviews with her every night. 

You can’t talk about Madonna without talking about her ever-changing beauty look, and these are a few of my favorites. 

Breathless Mahoney Madonna

[Buena Vista Pictures]

[Buena Vista Pictures]

Madonna mimicked Marilyn Monroe for a big chunk of her career, but she was never soft and vulnerable like MM. I love how she took the major components of Marilyn’s style—the platinum curls, the gowns with matching furs—and used them to shape her portrayal of Breathless Mahoney in Dick Tracy. She blended the ‘30s, ‘50s and early-‘90s to create an unforgettable look.

1995 VMAs Madonna

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One of my favorite Madonna beauty looks is the one she wore to the 1995 VMAs. You know, the one where a wasted Courtney Love interrupted Madge’s interview with Kurt Loder and Madonna powers through like an ice queen power bitch? I am obsessed with that voluminous ponytail. Khloe Kardashian wears that style all the time now.

Blonde Ambition Madonna

Remember LaserDisc?

Remember LaserDisc?

Speaking of iconic ponytails! During the Blonde Ambition tour of 1990, Madonna wore loads of John Paul Gaultier and MAC’s Russian Red. This is definitely one of her most famous incarnations; when you mention Madonna, someone will eventually reference the Cone Bra era.

Evita Madonna

[Buena Vista Pictures]

[Buena Vista Pictures]

Say what you will about Madonna’s acting career, but she looked stunning in character as Eva Peron in 1996’s Evita. The pencil-thin brows, dramatic red lips and golden blonde hair in a variety of late-1940s styles suited her bone structure perfectly.

Thick-Browed ‘80s Madonna

The Madonna who burst into our collective cultural consciousness in the early ‘80s lacked the polish of later incarnations, but that’s what makes her so charming. She had thick, untweezed brows, blonde hair with dark roots and a big, gap-toothed smile that promised to rule the world.

Late Aughts Madonna

[AP]

[AP]

Madonna took a break from changing it up for awhile in the late aughts and stuck with a flattering combination of touchable golden curls, pale skin and red lips, usually paired with soft, precise black liner. 

It was classic, but she could wear it with crazy Givenchy ensembles and look every bit as cutting-edge as she always has.

Ray of Light Madonna

[Maverick]

[Maverick]

My favorite Madonna beauty look was her Ray of Light period in 1998. 

After the birth of her oldest daughter Lourdes (a doppelgänger of her mother who is attending college in Michigan!), Madonna became involved in Eastern mysticism and also in Kabbalah and released one of her best albums, Ray of Light. She let her hair grow long and wavy and wore less makeup. On the cover of the album, she looks earthy, content, goddess-like. (She’s also wearing xoVain favorite Clinique Black Honey Almost Lipstick!)

Honorable mentions: “Like a Prayer” Madonna, “Express Yourself” Madonna, “Confessions on a Dance Floor” Disco Madonna!

  • Do you love Madonna, or has she never been your thing? 
  • What are your favorite Madonna beauty looks?