I learnt quickly while growing up that appearances do matter. My school teachers seemed eternally suspicious of me, as if waiting to discover some illicit agenda behind my antics that amounted to no worse than getting lost in Stephenie Meyer's seminal works in the middle of a lesson, or seeking respite from accountancy lessons in the institute’s art studio. The resulting punishments never seemed to fit the crime.
One day I realised why. A teacher commented that my thick kohl-lined eyes and eye-wateringly short skirts had already established the brightness of my future (without any actual evidence to back this theory up). The comment had the opposite of its intended effect—I still revel in being branded difficult based on how I present myself to the world. Chalk it up to a congenital penchant for challenging authority.
In this pursuit, I try to live up to the examples set by the sartorial rebels I admire, from author Fran Lebowitz and designer Miuccia Prada to actor Marlene Dietrich. They are all prime examples of ‘difficult women’ who represent beautiful contradictions in fashion that would perhaps make most people with conventional sensibilities baulk. As the author Cheryl Strayed explains, they are “brave enough to express the full range of one’s humanity and be ambitious, defiant, incorrigible and slightly badass”.
These ‘difficult women’ represent beautiful contradictions in fashion that would make most people with conventional sensibilities baulk
Lebowitz’s acerbic wit is matched by her sharply tailored suits, custom-made on Savile Row by Anderson & Sheppard—coincidentally, the same tailors who crafted Dietrich’s signature look. The bestselling author hasn’t deviated from her trademark uniform in five decades, rejecting ephemeral trends and traditionally feminine mores with equal disdain. The result? An aesthete who approaches fashion brain- first, one who doesn’t feel the need to minimise herself just so others feel comfortable in their prejudice. It’s a motto Prada would agree with. Her namesake brand has achieved cult status for challenging the notion of ‘pretty’, and the designer herself sticks to her favoured pencil skirts and finely knit jumpers, even when posing as the cover star for Vogue. Despite feeling torn between the contradictions of her day job designing luxury products and her political activism, she’s rarely apologised for where her inner compass has steered her. The member of the difficult women’s club admits that not wanting to do what everyone else is doing is “probably really deeply a part of myself ”.
When the world zigs, difficult women zag. “When I started to wear what made me feel good rather than [be guided] by what the world thought I should look like, I discovered my identity,” explains Seema Anand. The internet’s favourite sex educator wears handloom saris and extravagant bindis— hallmarks of the demure Indian beauty—while insisting on Instagram that women prioritise their orgasms.
For these women who have dedicated their lives to going against the grain, clothes have proven to be a beautiful armour that furthers their agenda. Thanks to them, fashion still feels like a healthy ecosystem that contains all shapes and sizes and allows them co-exist together. In my life, I’ve learnt that it is a much happier endeavour to look for validation within than to try to fit in. As I walk to work, my combination of a white button-down shirt paired with knee-high socks printed with hearts still raises many eyebrows on the streets. But I am committed to building a wardrobe that defies public approval, especially on what a Vogue editor should look like. It’s satisfying to team a flirty micro-mini skirt with a boxy men’s shirt rather than giving in to the symbiotic relationship the skirt has with a form-flattering tank top. After all, originality trumps obeisance.
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