Madonna’s 10 most iconic looks of all time

Growing up, fashion was an all-inclusive experience, but carving out an identity away from the norm was a luxury not every one was ready to embrace. Tidi Benbenisti reminisces about her circa ’80s style icon, Madonna, and how personal style – then and now – calls for breaking boundaries and being brave

Growing up, pop music was never really my thing. As much as my friends crushed on boy bands (past and present), I preferred the likes of Daft Punk, David Morales, Frankie Knuckles, Todd Terry and Teddy Riley. Latino music still rates very high (because Spanish was spoken at home), and a whole lot of disco made me smile (and still does).

But as luck would have it, my music influencers didn’t inspire a collection of branded clothing to be bought from fan clubs or department stores, and so my dedication to their creativity was reflected in my LP and cassettes collection (yes, we are talking a couple of decades back before I even heard of a CD, and a time where downloads would have been associated with removal of furniture off a truck). And it was a project – Dress Like The Icon You Don’t Know – that led me to provocateur Madonna (Louise Ciccone): the aspiring dancer who transformed popular culture and influenced at least two generations with her commercial sound and fearless approach to life, present company included.

Her music (in the ‘80s) was the epitome of pop, but it was her fashion that piqued my interest and her fearless sense of self and style that intrigued me even more.

Before the Icon project, I was a safe dresser. I loved my super-skinny jeans and hotpants. I loathed shoulder pads (and I still do). I wore (black) miniskirts and bodycon dresses (pre-Herve Leger days) with loafers or heels in pastels and brights. These were possibly bold choices but they were not groundbreaking because there were no accompanying fishnet stockings or fingerless lace or leather gloves. And while there were cropped tops, they never revealed my midriff and were always worn over a tank top because my mother would have grounded me well beyond my 21st birthday. My wardrobe wasn’t home to bustiers or coned, fringed bras, not until I was 21. As for paisley, it was too psychedelic for me – until my Icon project research kicked off in earnest with the help of imported music magazines, Smash Hits and Number One.

In the mid to late ‘80s and Madonna’s fashion mood was a mix between ‘50s bee-bop and rebel rock. It was her short-lived marriage to bad boy Sean Penn that inspired True Blue, where she rocked a cropped platinum cut, and the music videos accompanying her chart topping hits True Blue, Papa Don’t Preach and Open Your Heart reflected a bold new take on self-expression.

Her looks segued from pretty (in a flared blue dress worn over black cropped leggings) to androgynous (cropped suit, jacket sleeves pushed up above her elbows, hat). She did street-style cool in nautical stripes, boyfriend jeans (probably her ex’s) and a biker jacket. In the days of Lucky Star and Holiday, she offered an accessible rock-meets-Goth look that was rebellious but not offensive. Those cut-off fishnet stockings teamed with a miniskirt and a cropped slogan Tee, layered with stacked rubber and leather bracelets and one supersized long earring, were fashion-forward.

Then I saw the music clip for Dress You Up In My Love, from her Like A Virgin world tour. I had all the necessary pieces hanging in my wardrobe, from the cropped lace leggings and the matching lace miniskirt to multiple necklaces and stacked bracelets (sans the crucifix); bed hair came naturally to me; and a brown eye pencil helped recreate the beauty spot above the lip. The only thing I needed was the one print I didn’t dig (psychedelic, man).

Madonna’s paisley jacket was as colourful and overwhelming as you could get. But there was something almost regal (wait, she would become pop royalty) and unequivocally bold that made it covetable. It terrified me, but at the same time no one in my circle of friends had. And so I gave my mother a reference I found in a magazine and off she went to find a paisley print and lining as close to the Madonna version as she could, to be sewn to my exact measurements.

In the week leading up to the Icon presentation, I needed extra courage to embrace the paisley bit. Only Madonna could pull off such creative chaos, and I was but a student trying to get a decent grade from a teacher who wasn’t my fan on a good day. Then I remembered how self-confidence took the Michigan native from obscurity to chart-topping star and I felt inspired to at least give it a try. one week later …

A single supersized long earring was the final touch before I entered the classroom. Anxiously I pressed play (miming to Dress You Up In My Love), and pretended the classroom was the stage and my classmates were my adoring fans. Determination and chutzpah resulted in plenty of laughter, and courage earned me an A. It also transformed me into a more adventurous dresser, who was not afraid to take a walk on the wild side of style.

The thing about Madonna and her style sensibility is that she doesn’t just walk the new path, she maps it out, constructs it, and calls in style engineers and briefs them on how it needs to be done. Pushing boundaries, raising the bar, daring to do and embracing one’s liberty to be her true self, unlike anyone else, is her trademark. It’s this very sense of freedom that I tend to forget to apply to my daily life, and which I need to be reminded of from time to time. And I do when I shop; I look at how items are displayed in the windows or on my screen, and ask myself: Is this me? Do I really want to look like that? How does this item work with my style sensibility? I sometimes suffer epic fashion fails, and it takes bravery to admit that, and sometimes I am asked ‘where did you buy that?’ No matter which side of the velvet rope I find myself on, I am content knowing that I felt confident in the way that I dressed and looked when I left the house… And if I made people laugh, oh, well, embarrassment makes way for the idea that I did some good, too. But, knowing that I can always switch things up wear those shoes with another outfit, or team the white blouse with skinny jeans instead – is a freedom, and that’s key to a happy (and style-savvy) life.

Today, I find inspiration in other places and faces, but one thing remains true in my fashion time capsule: Madonna, often controversial and provocative, has revolutionised the way I look at life, being a woman, expressing myself verbally and with fashion.

And for the paisley, along the way, I added more wearable pieces into my wardrobe. This summer I acquired a sundress adorned with paisley and, for winter 2016, I have a kaftan dress embellished with the twisted droplet in burgundy and mauve.

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