In about a week or so, as her MDNA tour comes to this part of the world, I’ll be watching the Queen of Pop strut her stuff on stage.  It won’t be the first time I’ve seen her up close and personal, but she never ceases to amaze me.  Love her or loathe her, she is a cultural icon the like of which we won’t see again in our lifetimes.

Her ability to push boundaries, reinvent herself and occasionally put out some pretty cracking music is legendary.  She is the subject of university degree courses, a feminist icon and a diva who gives good interview.  She is also a clothes horse, and I have given myself the impossible task of picking out 5 seminal outfits that she’s worn over the last 30 years.  So strap yourself in and get ready to disagree – it’s what the lady herself would want…

1. Desperately Seeking Status: If you’re going to an ‘80s parties and you see someone wearing lace gloves, lightly permed hair, a black string vest, a crucifix and several hundred rubber bracelets, you instantly know who they’ve come as.  For me, Madge’s look in Desperately Seeking Susan (which coincidentally remains her best movie) defined an era.  Having played with the looks from Borderline, Lucky Star and Dress You Up, they all came together in this movie (and the Into The Groove video).  I am sure that when she dies they’ll place a pair of lace gloves and a “Boy Toy” belt on her coffin; but – just so you know – if anyone leaves the Santo Loquasto jacket that Rosanna Arquette wore in the film, I’m nicking it.


2. Live to Surprise: Granted, this is an unusual choice, but for me, it was the first hint at Madge’s chameleonic tendencies.  Having just gotten used to her as a made-up vamp warbling about being Like a Virgin, here was the new Mrs Penn sporting a 1930s style floral dress, with pale make-up and shoulder-length hair singing a ballad.  Live to Tell gave Madonna her third US number one and showed people that her experimental dress sense was only just beginning to emerge.  It might have also given Dolce and Gabbana the licence to continually design an array of floral summer dresses season after season after season.



3. Strike a Pose: Everyone agrees that the Vogue video was pretty revolutionary in its simplicity.  Shot in black and white by David Fincher, it featured Madonna sporting everything from feathers to a see-through lace blouse.  But I think she has rarely looked as classy as she did in this simple, black trouser suit – the antidote to Jean Paul Gaultier.  Not a natural choice for someone to be vogue-ing in, but she werks it nonetheless.  As an aside, I still fail to see how she lost out in the 1990 VMAs to MC Hammer for “Best Dance Video”.  The mind boggles.

4. Ray of Hope: Having been in the wilderness for a few years and having/finding/buying a few kids, Her Madjesty came back in the late nineties with what many regard (including me) as her best album.  Channeling earth-mother hippie chic, she dressed in jeans, denim jacket and simple top and showed that there was someone before Kate Moss who could wear denim on denim.  I don’t know if William Orbit or Jonas Åkerlund had much influence on this look, but for me, the Ray of Light era represented Madge getting it spot on both in terms of her look and her music.

5. Time Goes By: Now when most people think of the Hung Up video, they think of “47-year-old-in-totes-hiddy-leotard-shock”.  Not I: for me, the bit I loved from the Johan Renck video is Madge walking along the street, having finished her warm-up in the dance studio, in skinny jeans, green top and tight leather jacket.  Very reminiscent of a scene from Papa Don’t Preach, but again showed Madonna’s zeitgeisty powers: she got it spot on and influenced a lot of 2005’s looks.  And the fact that she managed to persuade Renck to stop directing Kate Moss’s H&M ad campaign and shoot her video instead couldn’t have hurt: touché!

I’m pretty intrigued to see the costume changes on MDNA: it’ll be interesting to see how quickly the 54 year old can slip into spandex these days.  But whatever she wears, I’m sure we’ll all be polarised afterwards in wondering if she got it right…and I suspect she wouldn’t have it any other way.

About Ant0scar

Ant0scar first came to prominence as the inspiration behind Roland Mouret’s White Collection. Having subsequently turned his attention to writing, he has been twice nominated as best writer on Bohomoth and hopes to soon turn his love of short stories into a Day-Time Emmy Award, an Oscar and possibly a Grammy. When he’s not negotiating lower sauvignon blanc prices, Ant0scar enjoys socializing with Kate Moss, street-dancing and advanced dressage. He lives in exile with his husband on a barge with four imaginary Great Danes, a tarantula and a cardboard cut-out of Beyoncé. He must never be challenged...
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  1. Shiny says:

    J’adore, BOMO.

  2. Jr says:

    How about the Papa Don’t Preach striped top and leather jackets? Or the Keith Haring print skirt in Borderline ? Oh just too many to mention. Don’t know how you cut it to 5.

    • Ant0scar says:

      Agreed – the Haring influence was huge. Cutting it to 5 is impossible…other influences creep in. I mean, if we’re talking costumes, it’s hard to look past this…

  3. jojo says:

    I’m very fond of the Like a Prayer video …the long wavy dark hair and clingy dress.

  4. Guest says:

    Desperately Seeking Susan days were sure fun and bring back fond memories. Unafraid to try funky wear without a care.

    • Jr says:

      And cheap to copy. I did the whole Like A virgin in the gondola for next to
      Nothing. Just some Lycra tights and tubing! Loved it.

  5. Jameson says:

    Express Yourself did it for me. Think I had about 17 versions of that song, and at the time I even altered a suit jacket to fit like the one in the video and somehow even found an eye monocle on a chain. Where I was going to wear that stuff though??? lol
    I can still do all the dance moves though!

  6. Jameson says:

    No, from the actual video, the 2:00 mark.

    Dance moves from the video/concert, MTV awards combined. lol

  7. Jameson says:

    I thought the words from the song were true and inspiring, and kind of engrained in me, don’t go for second best…if the time isn’t right then move on…you’ll do much better on your own…

  8. twiggy twiggy says:

    It still enrages me that Madge lost Best Dance Video to MC HAMMER. It also lost Best Choreography. Twenty years on and whose video has become iconic, though?

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