6 Of Madonna’s Most Iconic Looks Decoded

To celebrate the 30th anniversary of Like A Virgin, we asked writer and Madge expert to talk us through some of the pop icons's most famous looks.

Bedtime Stories, 1994
After the furore caused by 1992’s fetishy, sexcentric Erotica album, Madonna opted for a subtler look for the next one. The gold-toothed-dominatrix persona invented for Erotica was replaced by this soft-focus sex kitten: her makeup is designed to flatter rather than intimidate, the tousled hair suggests she’s just had a pillow-fight rather than a bondage session, and that frothy negligee is straight out of the ‘50s. Shame about the nose ring, but it didn’t last long.

Who’s That Girl? 1987
Hair and eyebrows: she knew how to work them. This is from her 1987 film Who’s That Girl, in which she plays a squeaky-voiced ditz called Nikki Finn, who’s just served a prison sentence on trumped-up charges. Her look here is informed by wide-eyed ingenuousness. The fluffy hair – believe it or not, this was a genuine ‘80s style, kept aloft by clouds of hairspray – denotes innocence, and the ramped-up brows draw attention to her eyes. The film wasn’t a success, and she quickly dropped the look.

Like a Prayer, 1989
Like a Prayer was the first Madonna album that had critics thinking that she might be more than just a spiky pop kitten. Accompanying the more thoughtful music was a full-scale makeover: she went dark and enigmatic, playing down her youthful cuteness (she was 31 at this point, but passed for 10 years younger) and exaggerating her Italian heritage with darker makeup.

Evita, 1996
She made a convincing Eva Peron in the film Evita (and won a Golden Globe for Best Actress for it), partly because her malleable features lent themselves to a look that, in this case, was based on something more than conventional prettiness Madonna-as-Evita radiated strength of character – though her ‘40s and ‘50s wardrobe begat a minor fashion trend.

Holiday, 1983
The look that launched a million wannabes. From a video (never officially released) for the early single Holiday, it shows her in the thrown-together leggings, bracelets and belts that quickly became recognised as her signature style. It was easy to dance in – something that concerned the former dance student and avid club-goer – and, crucially, easy to copy. Millions of teenage girls did.

MTV Awards, 2003
She’s 45 here, and this famous kiss could almost be read as Madonna anointing Britney Spears as her successor, but no mortal being could “succeed” her. Rather, their brief peck was a bit of fun, with the added inducement of guaranteed headlines. Her sleek woman-in-black outfit and pulled-back hair emanate strength and confidence.

Madonna: Ambition. Music. Style, by Caroline Sullivan, Carlton £25, out now.

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