BY Eric Rezsnyak
As of this writing, Madonna has released at least 80 music videos, from 1982’s “Everybody” to 2024’s “Popular.” Over those dozens of videos released over four decades, the artist has served up a buffet of memorable looks, many of which inspired fashions and trends in broader pop culture.
In conjunction with our Best Madonna Music Video episode, we’ve gone through her video collection and picked out some of our favorite aesthetics worn by the erstwhile Material Girl. This was no small feat, and a highly subjective list. If we left out YOUR favorite Madonna looks, mention them in the comment section.
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Honorable Mention: “Material Girl”
On the one hand, it is a literally iconic look — this was one of Madonna’s breakout videos, and if you were alive in the 80s, you knew this outfit. But at the same time, it’s not really a Madonna look. This is a 1:1 recreation of the “Diamonds Are a Girl’s Best Friend” number from Gentlemen Prefer Blondes, with Madonna in the exact same outfit as Marilyn Monroe. Incredibly effective, especially the nod to a predecessor blonde bombshell whose sex life captivated the world. But in good conscience, I cannot consider it a Madonna look.
10. “Cherish”
This is purely personal, part of my ongoing #JusticeForCherish crusade. I don’t understand why this video is paid so much dust by pop culture in general. The song is a bop, it was directed by noted photographer Herb Ritts, and Madonna looks amazing in it. This is one of the more stripped-down versions of Madonna that we had seen up to this point (it was released in 1989, still in the first decade of her career), as she wears a simple button-up short dress. But it’s so effective as she splashes around in the surf, accompanied by merpeople. It doesn’t break new ground, as her best looks do, but she exudes vibrancy and joie de vivre.
9. “True Blue”
Another often-overlooked music video, “True Blue” is important because it helped Madonna expand her demographic beyond club kids and teenage girls by embracing the 1950s nostalgia that was EVERYWHERE in the 80s, and appealing to those girls’ moms. Seriously, I vividly remember my mother softening on Madonna because of THIS video. But let’s talk the look: there are a few here, the frilly blue-black polka dot top and the all-black bodysuit. Both are simple, but striking. The real deal here is that shocking white, close-cropped hair, a big departure from the messy, partially dyed locks she had been rocking up to that point. The platinum blonde would be Madonna’s signature hairstyle for much of the late 80s and early 90s, her most influential period.
8. “Die Another Day”
Madonna’s Bond theme is widely derided — as we say on our podcast, everyone is entitled to their wrong opinions — but this video is loaded with cool looks. First and foremost, the monochromatic fencing Madonnas looking effing badass. Super-spy Madonna being tortured is sporting the blend of menswear and athleisure that were her go-to look during that period. And boss-bitch Madonna in a cream-colored suit, aggressively wielding a cane, feels reminiscent of another iconic video later on this list. “Die Another Day” may be a bad movie, but this song and video — especially the aesthetics of it — are solid.
7. “Erotica”
Continuing the trend of Madonna videos/eras that were largely ignored or dismissed, let’s talk “Erotica.” This early-90s album leaned even more into sex, culminating in Madonna’s scandalous Sex book and the “Justify My Love” video, both of which were banned. And you better believe EVERYONE was talking about it. In the “Erotica” video, Madonna takes on the role of Dita, the mistress of a (presumably German) S&M club, wearing a sheer black top with a bright white collar, a playful face mask, a fake gold tooth (before they were cool!), and wielding a riding crop. It is an iconic outfit and arguably brought elements of S&M into the mainstream conversation.
6. “Into the Groove”
The actual clothes worn in 1985’s “Into the Groove” are not exceptional. They are, essentially, NYC streetwear staples from the 1980s. It’s what the best-dressed club kids were wearing for a night out at the time. But this video broadcast that look EVERYWHERE, and suddenly kids all over this country were dressing like Madonna. Young people copying pop stars is nothing new, but Madonna, in part through the power of this video, set the trends for an entire generation of young women. How impactful is the look from this video? I have a tank top from Swish Embassy featuring Madonna’s face from this video and I get comments about it ALL the time. Also, Madonna drying her armpits with a club hand dryer is, honestly, a fucking moment.
5. “Frozen”
This was the lead single off of Ray of Light, which featured a hard reset for Madonna’s entire image. Embracing the spiritual and maternal elements of her persona — she had recently given birth to her first child — Madonna gives us a mystical vibe with the down-tempo, moody “Frozen.” And she does so in style, decked out in several gorgeous gowns by Jean-Paul Gaultier — and that great necklace, also from the designer — wearing henna tattoos on her hands, and that great witch-like hairpiece. It’s beautiful. It’s cool. And she can transform into a doberman. Fashionable AND functional.
4. “Open Your Heart”
Your honor, she’s serving. One of the sexiest outfits Madonna ever wore — which is really saying something — the outfit for “Open Your Heart” is arguably simple, but also quite detailed. Black fishnet stockings, black heels, a bustier with betassled gold nipples, and then long black gloves — the only thing she removes during her peep-show striptease. We also can’t forget the short-black wig, that she removes to, again, that close-cropped platinum hair.
3. “Express Yourself”
My first question here is, Which look from “Express Yourself”? And my answer is: all of them. Madonna has multiple iconic looks from this David Fincher-directed video, including but not limited to the chartreuse gown referenced above; the 1920s-style men’s business suit with the monocle; and of course, who could forget: cone tits. It is an aesthetic FEAST, and I lapped it up like a bowl of milk.
2. “Like a Virgin”
There are two distinct outfits in this Venice-set video, Madonna’s street clothes as she boogies on a gondola (very much the same vein as the looks we referenced in “Into the Groove”) and then the over-the-top 80s wedding she wears to roam about an abandoned villa, waiting to be approached by her man who may or may not be a lion. (Just go with it.) We’re specifically talking about the wedding dress, which would be referenced in Madonna’s “Like a Virgin” performance at the inaugural MTV Video Music Awards, and which was, again, a critical pop-culture landmark for Madonna. The actual details of the dress are not hugely important. But Madonna being swallowed by piles and piles of white satin, taffeta, and lace — that is a key image that has been replicated over and over.
1. “Take a Bow”
Exquisite. Stunning. Flawless. This is Madonna at — as I said in the podcast episode — the peak of her aesthetic power, bringing in top-class designers. Suit by John Galliano. Shoes by Christian Laboutin. Additional clothing by Donatella Versace. Everything about this video feels meticulous, and Madonna looks breathtaking throughout, from her reserved society lady watching in the stands, to a lonely woman writhing in bed wearing some of the sexiest lingerie committed to film, to a beaten and broken woman running to her freedom. Madonna never looked better, and 30+ years after its release, the aesthetics of this video remain as powerful as they were the day it was released. A timeless masterpiece.
