Wearing heeled boots to play frisbee amidst uneven ground and dog poop.

I don’t usually wear heels in Singapore for a few reasons. Practically speaking, since I only passed my driving test three days before flying off, it was a pain to walk out and take public transport with the soles of my feet contorted for the whole day. I’m significantly taller than some of my closest friends and I can feel a little crick in my neck looking down at (not on) them for extended periods of time. And once I wear any heels higher than an inch or two, I pass the 175cm (or 5′9 for my imperial friends) barrier and get weird stares on the street. 

Maybe I was imagining it, maybe it wasn’t quite to that extent. Maybe my fly was down or I had food all down my front and that’s why people were giving me weird looks. Fact is, though, that when I’m in Singapore I feel constantly observed and judged on my appearance by societal eyes peering disapprovingly over a pair of precariously perched norm-framed glasses. This particular kind of judgment is made not so much based on how attractive a person is, but more based on how a person’s appearance seemingly reflects their personality and morals. 

We are all, to some extent, guilty of perpetuating this. A point of note when we were doing The Great Gatsby (oh what a surprise) in Commerce class was that Nick Carraway states that he has a tendency to reserve judgment, but in no way does this make him an impartial observer. In the same vein, even if we do reserve our direct judgments, we convey our valuations through other social cues. Stares, for one, and questioning looks. Innocuous-sounding questions that peel back a layer to reveal criticism stewing underneath. Whispers of ‘what on earth is she wearing’, ‘no sense of style’ and ‘so trashy’ flying like little bees from bonnet to bonnet. 

This kind of judgment is obviously nothing new, nor is it anything that can be stamped out by the hand of anti-discrimination based on pure decree. I’m guilty of it, you’re guilty of it, everyone’s guilty of it except maybe the Dalai Lama. (Confession: I spelt that as llama at first.) 

The degree of it is totally different here in New York, though. It’s to be expected - capital of liberalism, hotpot of flowing creativity, bastion of diversity and all the other slogans Jay-Z basically listed in Empire State of Mind. Part of it’s probably also that people are too busy doing their own thing to really care how crazy you look, and having bright purple pants or a top hat isn’t nearly as out there as the pigeon man in Washington Square Park or the back of a guy’s trench imploring the world to fuck itself. 

And maybe it’s just my idealism talking, but part of it’s probably also that they take an outfit or appearance for what it is instead of what they think it is. I’ve been getting a lot more compliments on outfits here than back home, even from random strangers, and it (feeds my ego) reflects both the culture of affirmation and attitude that people take, as well as how much more conducive the environment is. I dress in whatever I feel looks good rather than a compromise between that and what I think other people will deem appropriate, and consequently I feel a lot more comfortable and content. It’s not about wearing a tutu to class to catch attention or dripping brand names as evidence of exercising a parent’s credit card. It’s not about showing skin or wearing tight-fitting clothes, it’s about wearing something other than the national uniform of shorts-tops-flip-flops and not feeling silently persecuted for it. Here, I wear my 2.5 inch-heeled boots almost daily and no one bats an eye. 

Definitely, the weather has a large part to play - no one can really be bothered to dress in a style other than comfortable when avoiding sweat stains and melting makeup is the priority. But back home, there’s almost an aversion to being well dressed even without these taking concerns into consideration. The question “Why are you so well dressed?” is almost an accusation of inappropriateness despite the complimentary-sounding description. I’ve been asked repeatedly “Why are you wearing heels when you’re already so tall?” as though something’s wrong with wearing heels once you’re past a certain base height. It’s not because of a conscious maliciousness, but more an ingrained alarm system that blares a lot more sensitively in some places than others. 

I can’t blame my dressing in either environment solely on the environment, and I can’t deny my own role of merely perpetuating and echoing the atmosphere of each environment. And looking back at my ramble, so many of the statements I’ve written are so general that I can probably lead a few armies soon. But I’m going to try to take whatever comfort and self-confidence I derive from dressing freely here back home and wear heels whenever the hell I want without caring about judgment. And hopefully when I care less about judgment I’ll project less of my own judgment, and maybe one day there’ll be one less pair of eyes peering through those glasses.

Who says wearing heels restricts movement? 

Top and pants | Zara

Sunglasses | Ray-Bans

Photos | Fede, Jason