Musings of a Singaporean Transgender

It's been quite a few years since Isabelle first stepped out in public. I still remember the thumping in my chest, the fear of being recognised as a guy wearing a dress, the shame when someone stares at me for longer than usual and the euphoria of unexpected validation. But mostly the fear, which wells up from the gut up to your throat and paralyses both the mind and body. The first time out in public was so very scary. But I've gone out in public many times since that faithful Halloween of 2018 and I feel a lot less stressed when I do so now as Isabelle. 

Don't get me wrong, going out en-femme still has its stressful moments. Stepping out and returning home as Isabelle is always the most stressful because I really don't want my neighbours to see me. I still don't like eating out as Isabelle because I'll be seated in close proximity with other patrons who can gawk at me with impunity (more importantly, the long hair really gets in the way). And being stared by multiple uncles/aunties in quick succession at the shopping malls still throws me off a bit. But I'm no longer uptight about stepping out and feel relaxed most of the time. There are a number of reasons why this is so. I've gained more experience being out in public and honestly, Singapore's a pretty good place to crossdress since it is safe and people generally mind their own business. I've improved my skills since 2018 and confident that my style allows me to blend in the best I can. I'm also a bit older too, so there is the element of YOLO where I don't really care as much about whether people realise I am a guy in a dress or not. To top it off, mandatory mask wearing due to the Covid pandemic has allowed me to hide my manly lower jaw and larger nose, which helps me to blend in even more. 

Although being in public puts a crossdresser in a "riskier" position of being recognised as male, a lot of this risk isn't consequential unless it is a partner/friend/relative/colleague who recognises you. And usually if it is your friend, I'd think they'll generally be understanding and supportive of what you do. The upside of going out in public en-femme is that I get to do a lot more regular day to day things as a woman, with shopping right at the top of the list. It also creates opportunity for validation, which is something that so many of us crave. These moments are usually fleeting and insignificant to any other observer, but to us crossdressers who aren't fully out yet, it means a lot. Even something simple like being called Ma'am by the bouncer at the club during my first time out in public was validating. My makeup was middling at best, my wig was unnaturally shiny and I could barely navigate in my 4 inch heels, but it still felt great. 

I've since had multiple occasions where I interacted with other people who seem to be perfectly comfortable with Isabelle. A sales assistant giving me a small nod and smile when I picked out items to try in the changing room. The bridal studio's makeup artists and photographers who were casually chatting with me throughout the entire photoshoot, occasionally telling me that my female self looks pretty decent (service for the paying customer perhaps. But the comments didn't come across to me as fake). I've also had a lot more close encounters with random strangers recently when I visited iWan Selfie Studio in March 2022, due to the relatively small studio and the close proximity which I have to be in with other patrons. I don't attempt to use a "girl-voice", so whenever I spoke everyone else in the room would be able to clearly tell I was a guy, but none really bat an eyelid about it. Most of the ladies just gave me a smile when we occasionally made eye contact and went back to busy themselves with dressing up and taking selfies/tiktok videos. 

Two episodes at the selfie studio were especially validating. The first was when I overheard a bunch of 3 young chinese gals commenting among themselves about wanting to take photos in the 2D themed room I was in. I wasn't too keen on the room so I told them they could use it and one of the girls went "Ehhhhh, 你是男生!" (the Chinese equivalent of "Omg you're a guy?!"). Inside I thought to myself, YESSSS I passed 😆 (the ladies were quite self-absorbed so they probably didn't pay me much attention earlier). Another episode was during my 3rd visit to the selfie studio on a weekday, when a gaggle of aunties in their 50s who were just done with their session were hanging around the lobby and chatting with the owner about the package prices. I had picked out a sequined bodycon dress which fitted me surprisingly well and started taking photos in the kaleidoscope tunnel. A few of the ladies started observing, commenting to each other out loud about my slim figure, about the poses I did, how experienced I must be, about the more professional mirrorless camera used (It was very Singaporean auntie behaviour). I was so embarrassed and taken aback when 4 of them suddenly whipped out their own phones to take photos of me, that I stopped my own selfie-taking to engage in a bit of a conversation with the curious aunties. It turned out they truly thought my look was well put together and just wanted to take some photos (unacceptable from a personal privacy standpoint, but understandable when you view them as harmless Singaporean aunties with a compulsion to take photos of anything and everything). One of them requested for me to take a selfie with her, while another requested for me to do a twin pose with her in the kaleidoscope tunnel, both of whom I obliged. Another eagerly showed me the slow-motion view she took in the starry theme room and told me I absolutely had to do the same thing. They were also genuinely interested to find out how I remotely controlled my mirrorless camera using my phone. I resumed my phototaking, which got a few more ooos and ahhs from the aunties before they left for their belated lunch.

To suddenly have random people wanting to take photos with me because they thought I looked pretty was incredibly weird but trippy. I've never had so many compliments about my looks in my entire life, which threw me off but definitely felt validating. I know this all sounds superficial, but there is a tinge of pride when I think of the effort I put in to pass and how far I have come since my pre-coming out days. When I shared the strange episode with my wife later on, she quipped that I was the drag queen in a sequin dress that everyone wanted to take a photo of post-performance (LOL 😂). Perhaps that was the reason why they wanted to take photos of/with me. I'm uncertain if the aunties figured out that I was a guy or not though. Some of them surely did but never mentioned to me. But being able to just engage people normally without them sounding weirded out or giving me a puzzled stare is great. 

I wouldn't start putting myself in situations where I have close encounters with others, like going to a bar and actively chatting with others. Although most people wouldn't mind, not everyone is so accepting of crossdressing behaviour.  Nor do I want to be out to my family/friends yet, and sure as hell not to my work colleagues (Knowing about my dual-life as Isabelle still remain a "need-to-know-only" basis). But I'd continue to do more regular things as Isabelle and enjoy every moment of being her without a care of being clocked (up to a point). And if there is a need to strike up a conversation with others in my baritone, I definitely wouldn't mind doing so.

Although this seems to be an easy question to answer, I do get asked more frequently that I expected. They're mainly asked by those in the closet, although some who have a bit more experience dressing up do ask me occasionally as well. 

There are some dedicated clothing shops for crossdressers online, originating in the USA or United Kingdom. However, I do find that these shops seem to be a product of an older era, when it was much hard to buy items online and anonymous delivery or self-collect from delivery lockers (e.g. POPStations, Ninja Collect, Blu, etc) was not an option. Marketed towards crossdressers, the range of available styles are narrower and tend to be a lot pricier for equivalent items sold in regular brick and mortar shops for women. Nevertheless, they do have certain specalised products which can be very good (e.g. high quality silicone hippads), niche outfits that appeal to certain segments of the community (e.g. 100% satin or latex maid outfits, super frilly petticoats, ballet stilettos) or outfits for crossdressers with very large and masculine physiques. For regular day to day clothing however, you're better off buying from the large number of options that women have. I've tried to list down the various choices available to crossdressers and why you may want to go for them.

For crossdressers who have started to step out in public, big clothing chains such as Zara, Mango, Cotton On, H&M, Uniqlo, etc, are fantastic to shop at. The selection is massive, there are frequent discounts and the clothes are regularly refreshed so you can come back in a few months to whole new range (yes, fast fashion isn't great for the environment I know). One of the best parts is that sales assistants generally don't both you, and because of the large floor area you can do your shopping without bumping into other patrons. Not that it really matters too much, since the ladies in such shops are usually absorbed in picking out clothes, while the men are just wandering around in boredom or scrolling through their phones. 

Unfortunately, if you're still in the closet, you may need to purchase clothes without being able to try them, which is a real bummer as the clothes may not fit well. Return policies are quite liberal, but that means walking up to the counter staff again in guy mode to ask for your slinky sequin dress to be exchanged for a larger size. Very nerve wracking for the newbie crossdresser.

I haven't gone into such small shops because I still feel nervous about interacting with sales assistants using my guy voice as Isabelle, and I know I will feel obliged to at least buy something if the sales assistant is super friendly and accommodating. To save my wallet, I've largely avoided such small shops. But I know crossdressers who have done so and they find the experience great. You'll get the full attention of the sales assistant who is eager to help you out and let you try on the clothes, in order to close a deal. I think sales assistants are also usually bored out of their minds.

Just because shops are smaller does not mean that you will not be able to find clothes that you like. The benefit of smaller shops are that the clothes could potentially be cheaper, negotiation is possible and they may hold certain range of clothing not typically found in the big clothing chains (e.g. Taiwanese styles, Evening/bridal wear, some can tailor make outfits if you're willing to pay for it, etc). 

Oh free returns are really the best when it comes to online shopping. Zalora and Asos were such important platforms that helped me to try on a wide range of outfits when I was still in the closet and unable to shop in person. I was able to order a larger selection of clothes and only keep the outfits that looked good on me, which helped to keep my crossdressing expenditure down. They helped me to gradually figure out the types of outfits that worked for my body shape and allowed me to explore styles that I would normally have not picked as a 1st or 2nd choice. In addition, the selection from these shops are massive and sells everything a girl needs; you can buy dresses, tops, skirts, pants, undergarments, sleepwear, accessories, makeup, brushes, bags, etc from either sites. Currently, around 80% of Isabelle's wardrobe is purchased from Zalora and Asos, which is pretty significant. Zalora has amazing delivery speeds locally; there were days that I got the package the next day even though I didn't sign up for next day deliveries. Buying from Asos will mean you get your goodies a bit longer, as they need to be shipped from overseas. Asos also tends to be more expensive than Zalora, although the quality and range of their clothes can be even larger (e.g. I could never find proper sequin dresses on Zalora, but Asos has loads of them).

Zalora did change it's free returns policy in 2021 to a conditional free returns policy of minimum $50 purchase however, probably due to the large number of people abusing the free delivery and returns policy. To make sure I qualify for free returns, I usually make a massive order from Zalora (like 15 outfits) and throw in some guy clothes I actually need for good measure. This way, all it takes is for me to keep 2 outfits to cross the $50 threshold. 

(This is the model, not me)

Point of caution though, unlike Zalora and Asos, such shops may have fancier packaging and sometimes state the contents of the package within them. If you currently live with your parents and the shop you want to buy from is unable to deliver them to a self-collection delivery locker, you may want to give the shop a miss. 

There are a few downsides with using these platforms though. If you don't like an item or there are defects, returning such purchases can be a pain in the butt, especially for Taobao. Although some crossdressers like to buy dresses from Taobao, I find shopping on the platform tiring as cheaper shops have the bad habit of using photos nicked from other places, while more expensive shops with better quality clothes can end up being pricier that buying locally. As such, I only buy items from Taobao that I cannot get from local shops, such as wigs, cosplays, breastforms, clip-on earrings, unique lingerie and large sized high-heel shoes (Local shops only sell up to size 41, while I am a size 43). I generally treat my purchases from Taobao as disposable. 

Do take note that Lazada and Shopee has this bad habit of stating the contents of the package on the delivery label, which is very annoying if you live with your parents and are delivering to your home. Taobao does not have this problem. The other downside of using Taobao, Lazada and Shopee apps, especially if you do so on your guy mode phone, is that ads for items your browsed on these apps will bleed all over the place. I've seen cheongsams and wigs recommended to me when I was reading the news on my BBC app. Not great if trying to be discreet.

I added Shien to this category, as it feels like an English-language site for clothes sold on Taobao; massive range of clothes and budget friendly, but quality is a dice roll and the photo of models look like it was nicked from somewhere. I personally haven't bought any clothes from Shein, but I have heard a mix of good and bad feedback from other crossdressers. 

I've done my fair share of browsing on Carousell and find quite a number of clothes from popular local clothing brands being sold. This means that if you're hankering for a particular outfit from a local clothing brand, there is a chance you'll find it on Carousell. The downside of course is that the seller may not have your size. In addition, I find that the listing price has a tendency of being only at a slight discount from the original price it was retailed at. Nevertheless, being a 2nd hand online shop, a good deal is bound to pop up every now and then.

Refash is a decent option for buying clothing on the cheap if you don't mind wearing something second hand. Their selection is decent and the price is wallet friendly too, which is very important for us occasional girls. The downside of Refash however is that you have to shop in person and it is like trawling through the bargain bin; you don't know what you'll be getting and if you do see something you like, it is the only piece and there's a chance it might not fit. So go in with zero expectations and you might turn out to be lucky.

After a while, you'll come to realise that buying clothes isn't the difficult part for crossdressers. It's making the most of your money and spending them on items that fit you properly, rather than wasting money on outfits that don't look good. It is important to know your body type, measurements and styles that flatter your body, rather than outfits that look great on a svelte, doe-eyed model in her early 20s. Pretty girls can wear a gunny sack and still pull it off, so if you do buy clothes online, try to cover the model's face, or try to imagine whether the outfit will still look good if it were 1 to 3 sizes larger. Takes a bit of practice and wasting some money buying stuff that doesn't work, but you'll get there eventually.