If there was a meme or a gif of a woman whipping off her bra while ‘Young Hearts Run Free’ plays in the background, it would be me. And I believe that I’m in the majority here. 

I’m one of those women who deliberately buys items of clothing if it can allow me to function braless (ruffle tops, I see you). I fully embrace my small boob privilege as much as I can help it. When I do wear bras, my rule of thumb is to wear whatever that helps me forget it’s there. No pinch of underwire, no scratchy bits, no padding to accumulate a valley of sweat rivulets. 

I wasn’t always so laissez-faire about lingerie. In fact, there was a time where my cute-bra obsession manifested in overflowing drawers. I was in my early twenties, figuring life out, and my bras reflected that: bras with multifunctional straps which I only wore one way, neon bras that were practically luminescent, sporty chic bras a la #mycalvins, push up bras for my modest cleavage, lacy concoctions that quickly looked worse for wear after they went through the wash. 

Lingerie shopping wasn’t cheap, but a lot less guilt-ridden than my other purchases. It’s underwear, I whispered to myself as I ran my hands over racks. You wear it everyday, plus you’re buying something that makes you feel good. Lingerie is self-love, I said. Lingerie is empowerment. 

It took me awhile (and too many dollars and too many bras) to realise that I didn’t exactly believe that. I adopted this mentality largely due to my consumption of ever-present lingerie ads both on and offline, and the growing movement of mindfulness and self-care. But while I did acknowledge that some lingerie flattered my body more than others, I wasn’t sure if it made me feel more confident, or powerful. If it wasn’t a special occasion, my everyday bras were an afterthought.

Underwear is a funny thing. For something that no one sees except yourself and possibly a significant other, society has been undeniably preoccupied with women’s underwear. Clothing has always been gendered, but arguably none more so than underwear, because for a long time, it was aligned with how people believed a woman should look. 

Allow me a (very brief!) history lesson. There were the wasp-waist corsets of the 1890s, and the S-curve corsets that pushed the bust up and the bottom back. The corset evolved again to flatten and slim hips for that 1920s flapper girl, boyish silhouette. 

It didn’t stop there: there were corsets with built-in pockets for women working in the auxiliary air force in World War 2, the bullet bra in the 1940s, and the pin-up girls in the 1950s. 1968 was the year the ‘bra-burning’ trope was born at a protest against misogyny and the Miss America pageant. And believe it or not, in the 1970s a bra was invented with fake nipples for “that sensual no-bra-look”. Google to believe it.

I can remember the first time I bought lingerie for someone other than myself. A well-intentioned older friend, scandalised when she saw drawers of my non-matching granny underwear, thought she would do my then-boyfriend a favour. She took me shopping, chose lingerie that I would never have picked for myself, and told me: “He’s going to loooooove this!” Tongue-tied by awkwardness, buoyed by her enthusiasm, I bought bras that I don’t remember and doubt I have worn past the year we were together. I remember the flush of heat above my collar when my ex thanked our friend in a manner that read: I’m joking, but not really. 

Looking back, we were both (literally) buying into the message of lingerie being bought for the person who would be seeing it, and not for the person actually wearing it. 

But can you blame us, considering the barrage of mass media that enforced this belief years ago? One of the most famous (or infamous) billboards was a Wonderbra billboard poster in 1994, rumoured to have caused traffic accidents because of gawking pedestrians and drivers. It featured model Eva Herzigova in a push-up plunge bra, looking down at her cleavage and smiling in coy delight. The poster read: “Hello boys”. 

Deemed iconic in the 1990s, it was given an overhaul in 2019, on the ad’s 25th anniversary. The new advert shows a model wearing a strapless bra making direct eye contact with the camera, with the text, “Hello me!” It was meant to herald “female self-empowerment”. Instead, it was mocked for celebrating an ad that carried a message which was sexist and archaic.  

“So much of the old ads about pleasing men resonated with me so badly that now I automatically ignore all lingerie ads,” one said. “I can’t get away from the fact that lingerie is also bought for the other person — it’s just too ingrained in me to believe I’m buying it only because I think it looks good,” another shared. 

This association is understandable, but also unfortunate, considering the commendable, concerted effort that has been made by underwear brands around the world. The key messages now are comfort, body confidence, and representation. Push up bras are making way for bralettes, T-shirt bras, and activewear, brands like Savage x Fenty are embracing diversity in models, and there has also been an increase in inclusivity with the sale of underwear bottoms for pre-surgery transgender women and bras to accommodate a wider bust. 

It’s an ethos echoed by local lingerie labels, whom I reached out to find out more about their brand messaging. “A lot of Instagram followers notice us because of our body positive brand message. However, they stay because they know we are committed to that cause,” says Chow Li Ying, the woman behind Our Bralette Club, which also offers custom-sized bralettes. “Good-looking things always sell, but the foundation of all our designs is always comfort.” 

Kate Low of Perk by Kate notes how lingerie has changed significantly in the last few years, and because of choice: “We now have a choice in designs — I can choose pieces that fit me, instead of feeling like I’m suffocating. 

Both shared anecdotes about customers with different needs and at different life stages (a nursing mum, a breast cancer survivor, a pregnant woman) who have shared how important lingerie has played in making themselves feel better about their body. 

Cynics should pause, because this was also reflected in some of the women I spoke to. While there were those who cared only for comfort, there were women who shared about the personal relationship they have with their underwear. One explained that whenever she felt down and defeated, she would put on flattering lingerie, even if she was alone at home. One said, “I love my lingerie. If I’m not wearing the right bra and feeling supported, I just want to go home.” Another shared that when she has a big day at work, she plans her entire outfit, lingerie included. “The outside must match the inside,” she quipped. “Pretty lingerie empowers me.” 

Ultimately, when it comes to something as personal as our undergarments, it’s unsurprising that the opinions run the gamut from ambivalence to emotional. What we wear closest to our skin is how we feel when we look in the mirror. For some, it’s that zing when you see yourself and think, I didn’t think I could look this good. For another, mirrors are only for after you’ve put the entire outfit on.

But the comment that stayed with me was from Sheryl Lim, founder of SUSY + BAE. When asked if she thought lingerie was empowering, she said:

Hold that thought, I said. What do you mean? 

She shared a story about being teased for being flat-chested in school, and for a period of time, thought maybe she didn’t have to wear a bra anyway. She told herself she didn’t care. But after eventually opening up to wearing bras that fit and flattered, she began to feel feminine, and realised that it was something she had always wanted to feel. “I hadn’t felt that way before. It empowered me because I let myself feel this way. I’m not that flat-chested girl — I’m a woman.” 

I had previously thought that because I didn’t get that lingerie zsa zsa zsu, it meant that I wasn’t fussed, or perhaps it just wasn’t the right bra. It’s a likely combination of the two, but it could also be me. I wasn’t expecting anything from lingerie other than pretty and functional (comfortable? Check. Not seen under my white top? Check.). But what if I allowed myself to consider that it could be transformative? What if I allowed myself to stand, just for a minute, in front of the mirror in underwear, and ask myself, what feels good? What looks good? What does my body look like, curves gently clasped in cotton, satin, or lace? 

In writing this, I realised that the fact that I cared so little about my undergarments just goes to show how far the industry has come. Ask me the same question a few decades ago and I would have a vastly different answer. It’s not to say that there isn’t a long way to go. When I heard about a friend having to buy ill-fitting boys’ underwear because there aren’t enough gender neutral ones on the market, it was a reminder of how we sorely need more inclusivity. We can celebrate the wins, and use them as ballast to do more. 

So I thought about what did make me feel good. A colourful sports bra that keeps the jiggle in. My period underwear, because it makes for one less thing to worry about. A kaftan, billowy enough to hide a food baby and an army of kittens. Things that help me get through the day as a woman. How odd, that underwear wasn’t a consideration for me. 

The next morning, I took my time to stand in front of my drawers to choose and put on a matching set of lingerie. I stood in front of the mirror. In the absence of social media, white noise about what I should look like, thoughts about what my partner might think if he saw me, I looked at my reflection. I thought: hello, me.

Writer's Note:

My name is Clara, and you can find me at @clarahow on the Dayre app. On my personal account, I write about the relationships I have with food, my body, and the compulsive need to document OOTDs.

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