In spring of 1990, Madonna‘s career and creativity was on an upward trajectory. She was already an international icon and had successfully made the transition from ’80s pop star to global megabrand. The singer’s visual component played an arguably huge role in helping her become a phenomenon, as she questioned, pushed and confronted many accepted societal norms. In the early part of her career, this was mainly via her own overt sexuality. Yet unlike many other female artists, Madonna was not simply eye candy.

Madonna’s Coat of Armour

While she became synonymous with wearing ‘underwear as outerwear’ – I have never seen a white men’s tank top and boxers look better than when she dons this combo in 1985’s Desperately Seeking Susan – it was her ability to transform these then daring looks not into something to simply be consumed by the masses, but to make them a coat of armour. I was seized with the overwhelming urge to appear at my junior high school wearing one of my dad’s oversized dress shirt with garters (note: this would not have gone down well with my Italian Catholic mother)- not because I wanted people (boys) to look at me, but because Madonna made her fashion and attitude about showing strength, confidence and a celebration of being a thinking, authentic self.

Madonna in Desperately Seeking Susan
This last part is the hardest to grapple with, as if you dressed like Madge, it was easy to be seen as a blind acolyte helping fuel the multi-million dollar Ciccone machine. But if you were brave enough to scratch below the surface, Madonna was all about questioning gender and expectations, whether that was strutting around proudly in masculine attire or piling on yet another rosary on an already bead-ladled neck. Madonna taught me acceptance, not by TELLING me I had to be different, but by SHOWING. In the aforementioned boxer outfit, she never says, ‘LOOK AT ME BEING SO TRANSGRESSIVE!’ She simply flops around doing her daily Madonna things, as if she was wearing a T-shirt and jeans, not men’s underwear, and a holy piece of jewelry from the Catholic church. This made the [engaged] fan ask themselves, WHY NOT?, or maybe more importantly, WHY? to not question tradition.

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Thanks to Marc