Crossdressers who are still in the closet usually tell me that although they want to go out in public, they are very afraid of doing so. I fully understand how incredibly scary taking the first step out in public can be. I was once in your shoes, overwhelmed with fear and constantly worrying that people will recognise that I am a guy (I blogged about my first time). Fast forward 3 years and after massive improvements in my hair, makeup and dress sense, people on the street still easily recognise that I am a crossdresser. But my anxiety is no longer a blaring siren in my ears nor does it paralyse me. It is still there for sure, but it is now just a niggling thought that I largely ignore. We are lucky that Singapore is a safe place to crossdress. The primary hurdle we need to overcome is the irrational fear that exists all in the brain. So fellow sister who is still in the closet. Assuming you have mustered the courage to finally take the plunge, here are some suggestions on where to go. (While some crossdressers do go to HDB carparks in the middle of the night, I'm not going to suggest it. You're unlikely to see anyone there, but it is a horrible first time location. What are you going to do? Walk up and down the carpark ramp in your stilettos while you melt in your wig?)

This is an awesome starting ground. Although getting to the bar itself might be a bit more challenging, once you're in the venue you can really relax a bit and be yourself. My first time out in public was to an LGBT friendly bar on the Halloween weekend. Even though I was sort of dragged out there and was so scared I was barely conversational, it did feel like a safe space, especially after the drag queens turned up. Although you are unlikely to meet other crossdressers (the community is tiny), a friendly transwoman or drag queen might decide to chit chat and give you a bit of encouragement.

If you're feeling a bit more daring, you could head to Clarke Quay. Try to aim for the Halloween weekend, since it is an excuse to dress up and be a bit sexier. Do remember to practice walking in your killer heels at home and bring out some plasters, or you'll be holding your heels and walking barefooted before the night is over.

As scary as going out in bright daylight sounds, shopping malls are pretty ok places to crossdress. Most people are there on errands and will mind their own business. If you want to be a bit tactical, pick a large mall with big name brands (e.g. H&M, Zara) and go there on weekdays when the shops open (typically 10am or 11am, depending on the shop). There's barely a crowd because most people are working or in school, and sales assistant really don't care about whether you are LGBT or not. Boutique shops can be a bit more unnerving since it is smaller and the sales assistants might follow you around, but remind yourself that they are just being friendly.  

Selfie studios are kind of a new thing in Singapore. While this is a confined space that isn't exactly a "public" location, you will still need to interact with the owners of the place and possibly give a shy smile to other customers you see there. The good thing is that the owners usually don't care whether you are male, female or transgender as long as you are a respectful, paying customer, and anyone you see there wouldn't bat an eyelid about your crossdressing, since they'll likely be in costume too. Note that selfie studios usually charge by the hour. 

This might be scary, but it may just be the fastest way to make friends (I recently saw a Trivia night organised by the Katong Queers that looks really fun). I've also heard of group meet ups in the LGBTQ community for BBQ, board games and other very casual, non-bar/clubbing events. While I haven't joined any, with the LGBTQ community opening up more and more in Singapore, I think this could be a good starting point. 

I feel that cosplay is akin to a gateway drug for crossdressers going out in public. While I personally haven't gone to any events, quite a number of local crossdressers start off here. It can be a bit scary for a first timer, but with everyone just dressed up as their favourite anime character and having fun taking photos, it is a pretty safe starting point. Taobao has also significantly lowered the barriers of entry to cosplay since you can just buy off the shelf costumes. Might need a bit more courage than say....a carpark in the middle of the night. But you know, carpe diem right?