Getting Out and About: Some Top Tips

This post will be added as a permanent page but in the meantime I thought you would like to see it as an ordinary blog post as well.

Many trans people feel the need to get out and about as their true selves but are often held back by fear and uncertainty. Will the local populace gather with pitchforks and torches ready to chase you down the street with your broken stiletto in one hand and your mascara infused tears streaming down your cheeks? Or will the local police station’s ‘Tranny Squad’ be lying in wait  ready to grab you the second you step out of the front door?

These are very real concerns. I know. I had them. But they are almost always totally unfounded. The truth is as long as you are careful, confident and dress and act ‘appropriately’ you are going to be perfectly safe ninety-nine percent of the time (obviously local conditions may vary). Crossdressing is no longer a crime (in the vast majority of places) and in any event, law enforcement is so stretched that they barely have time to deal with real offenders, let alone harass innocent crossdressers. Disclaimer: the fashion police are another story entirely. Watch out for them, they will make your life a misery for even the slightest transgression. This photo with the dodgy Princess Leia-esque hair clips is a perfect example. The fashion police still have this picture on file and I live in constant fear that they will issue a warrant for my arrest!


Owners , staff and managers of most establishments are only too keen to have a paying customer regardless of what that person is wearing and most members of the public are too self absorbed to notice anybody else.

Getting out is thus a very real possibility. Having said that you will have concerns and these need to be dealt with. I am therefore pleased to present my ‘top tips for getting out and about’ that I hope will make life easier for some of you.

Make sure you plan. Plan thoroughly and leave as little to chance as possible. The following are things you may want to consider. When will you leave, where will you go, how will you get there, what will you do whilst out, what will you wear (I probably shouldn’t have to mention this but still), when will you come back, how will you get back, is your planned outfit appropriate for your age, the venue, the time of day etc, how will you pay for things, where will you change, will you go alone or with someone else, if so who?

The more you plan the easier things become. You are going to be nervous. You will get in a flap. The fewer decisions you have to make, the better. But be prepared to be flexible. Plans may need some changes be at peace with that. Have some ‘plan Bs’ ready in case of problems that may arise. You will not be able to anticipate every problem, that is also ok.

Choose your outfit carefully. You don’t want to be all glammed up ready for a night of dancing in a micro mini if  all you are doing is popping down to the grocery store. This will draw unwelcome attention. This doesn’t mean you need to be a slob, just dress appropriately for the time and place. If necessary take some time to scope the place out and see what other women are wearing at the time of day you intend visiting. Make sure you feel comfortable. You may experience some discomfort as a result of being ‘a fish out of water’, so don’t make this worse by wearing clothes that scratch and itch or are just plain uncomfortable.

If you are worried about how you will be received at a venue, there is nothing wrong with phoning ahead? This worked for me once or twice. I was worried that I may be walking into a lion’s den so I e-mailed and told them who and what I was and asked them if they had a problem. The big win for this is that when you do arrive the manager will usually treat you well and make you feel at home which helps if you are feeling anxious. It will also allay any fears you may have had and give you some confidence. You can also discuss troubling issues such as toilet usage, other clients and their possible concerns etc which gives you and your host a chance to think things through in the cool light of day, rather than in the midst of a potentially awkward and conflict fueled situation.

As a first timer it is always a good idea to choose your venue carefully. You want to find a place where you will feel welcome and not feel like you are sticking out like a sore thumb. Depending on your tolerance for attention you also do not want to be a curiosity. For my first time out, I found a local trans friendly gay bar and went on a night that had been designated as a trans party night. I was one of many trans people out that night. All of whom went out of their way to make me feel welcome. I did not stand out as there were plenty of us around and most were way more flamboyantly dressed than me. I thus blended into the background and had a chance to feel at home.

As part of your preparation have some fun shopping. Choose the right outfit. Look for fashion advice (if you have no-one to ask,  Google is  your friend). Look at pictures to figure out what will work as an outfit and then set aside some time to practice. Practice your makeup, check your outfit (take some selfies and make sure it works on you, what looks good on a supermodel may not work for you and mirrors don’t always give you the best impression). Finally practice walking in your shoes and make sure they fit. Don’t forget little details like jewelry, handbags and nails as these really finish a look off.

Of course it is best if you have someone who can help you with your look but we are not all so lucky, so in the absence of a female or trans friend to assist with make up, look up makeup tutorials on YouTube and you may even consider finding a professional to help, but I realise that this is probably a step too far for the person just starting out.

Set aside plenty of time to get ready. Depending on your level of preparation this can take a lot longer than you expect. An informal survey seems to suggest that most of us take around two hours to get ready for a trip out. Your first time may well take longer as you may need to redo things once or thrice. You have been warned. Start as early as possible. Take your time. Have fun. Most importantly, relax.

Make sure you have everything you need before you start. Also make sure you have all your clean up products before you start. Nobody wants to be running to an all night pharmacy at 2 am to get nail polish remover!

Make sure you plan your route from the house to your car (or whatever transport you are using) and that you remember small details like having keys, money, driver’s licenses etc and that you remember to lock the door behind you. You will be in an altered mental state. You will be nervous and excited. You will almost certainly have around 50 kiloliters of adrenalin coursing through your body. Mundane details will get forgotten so keep them at the front of your mind as much as possible. Don’t forget your phone, money or driver’s license. Seriously these are easy to forget especially if you are changing from ‘man wallet’ to your purse and handbag. If you are driving take your license. Sure, the picture doesn’t match and if you are stopped you will have some explaining to do. However if you don’t have a license and you are stopped you will get a fine and you may even get hauled off to jail whilst they figure things out. The fewer excuses you give them to make your life tricky the better. Most police won’t even look twice at you. They are too busy dealing with the real baddies out there.

You may want to consider bringing an emergency kit with you. I have never done this but some of my friends do. Basically it is a small back pack with a quick change of clothes (jeans, cross trainers and baggy shirt) and some basic makeup removal kit (wet wipes work well I am told). This will allow you to do a quick change in your car if needed. It may give you some confidence and allows an escape route if needed. But as I say I have never used this.

Please take some time to consider how you are going to pay for things. Handing over a credit card could be problematic, especially if it has ‘Mr’ on it. Credit cards may also result in a sales assistant asking for photographic identification (especially if the ‘Mr’ on the card is at odds with the ‘Ms’ in front of them). Cash may be an option but it could also make you the target of a potential mugging. So be careful.

When you are out remember that you are to all intents and purposes unrecognisable. No-one is going to associate the woman in front of them with the man they may know. You will just look too different. Obviously some details may still cause problems for you. I have already alluded to handing over credit cards and photographic identification, but there are other things that may get people to associate the woman they see with the man they know. Chief of these is your car, especially if it is an unusual vehicle or has been customised in some way, so watch out for that. being out with someone can also pose problems here. If someone identifies your partner and then sees  you, you may have an issue. Tattoos, scars and other identifiers could also be problematic so consider covering these if you can. Your voice is also going to be a problem but there is not much that can be done about that, at least not without years of practice.

Given that you are probably not going to be identified you are free to have fun. You can be yourself and not worry about being caught, even if someone you know is in the same mall or night club. So let your hair down, relax and most importantly smile.

Some things to remember that will help your presentation. Try to do everything in a ladylike fashion, don’t stride out when walking, don’t shout out across the mall to a friend etc. There is of course nothing intrinsically wrong with any of these acts but if you want to blend as a woman you will want to try and behave as a woman behaves. Bending down is tricky as is any action that you do reflexively so stay in the moment and think about everything you are doing.

As far as choosing places to go, the world really is pretty much your oyster. Obviously you will want to avoid inherently dangerous places. I always try and avoid places where large numbers of straight young men congregate to drink alcohol. The chances of stumbling across an inebriated  transphobic guy with a point to prove are simply too high and the consumption of alcohol seldom makes people more tolerant and accepting of diversity. But if you stick to places where a single woman out on her own feels safe you are probably going to be fine.

As noted above trans friendly gay clubs and bars are good starting points as they are accepting of trans people and you will feel safer and more comfortable. Just be careful, not all gay clubs are necessarily trans friendly, so you may want to do some research before arriving. Also, remember to be respectful towards those around you. It is really not cool to arrive at a gay bar and then crack homophobic jokes or make silly comments. This will not endear you to the other clients and will damage the chances of other transwomen being accepted at that venue. I have also been out to restaurants, casinos, shopping malls, the beach and theaters. I have always felt safe and have seldom had even slightly negative experiences. The casino (which has a shopping mall, cinemas and restaurants in the same complex) proved a surprisingly good choice. There is so much security that nobody is going to be aggressive with you and if there is a problem help is very close at hand. I suspect that museums, art galleries and other attractions will also be good choices.

A word of caution (and this is purely a personal thing) it may be a good idea to avoid places with high concentrations of children. The reasons are manifold. Firstly parents are justifiably concerned with their children’s safety and any threat to them will be met head on. Due to societal prejudices crossdressers and  other trans people are still sometimes considered to be perverts and we thus constitute a possible threat. We are unlikely to change this view in a conflict situation so it is best to avoid the conflict. Secondly children are almost certainly more likely to ‘clock’ you than an adult. Adults tend to believe what they see: looks like a woman, smells like a woman, it is a woman. whereas children are more critical and as they are still figuring out facial features they are more likely to see what lies under the presentation. Finally take your outing as an opportunity to do what you want to do for you. Speaking as a parent, this means doing non-child stuff. Go and see that art exhibition, or whatever else you fancy.

I hope this rather long list of top tips has helped. Shortly, I will also be posting a list of places that are worth visiting dressed. Obviously this list will only be of relevance to those in or visiting South Africa and Gauteng but it may help some others with ideas.


Add yours →

  1. Danielle I’m going to add four words to one of your sentences:
    “Your voice is also going to be a problem but there’s not much that can be done about that, at least not without years of practice”…so start practising now!
    You won’t get to the stage of being able to pass on the phone for years, if ever (I’m certainly not there), but it doesn’t take too much effort to get to a stage where the voice isn’t immediately jarring in person. If passing is your goal, there’s not a great deal of point putting in so much effort to make yourself physically passable if you’re then going to open your mouth and turn into Barry White.

    Liked by 2 people

  2. Sorry that autocorrected to Danielle instead of Daniella

    Liked by 1 person

  3. I see you wearing a pair of shorts. Then I remember, your not in the northern hemisphere. I solved the I’d and money issue for myself, just started carrying a purse all the time. It usual stays in the car until I get home aside from my wallet.


  4. A good blog Daniella. This is all good advice and by and large advice I have given to myself. I do agree with Kirsty re the voice. Yes it is difficult to alter our voice, God knows I find it very hard and I doubt very much if I fool anyone with it, but I suppose if it is soft enough people generally will accept what they see over what they hear. Also you are so right that if we make the effort to blend, well blend maybe is not the best term, but to be an average woman and not someones idea of a teenage supermodel, you pass through society with little or no notice being taken. Yes too many people are too wrapped up in their own wee world to notice very much.

    Liked by 1 person

  5. Good post Daniella! Lots of good thoughts for those of us not very experienced with going out. I look forward to more of this.

    Liked by 1 person

  6. I have this to say. From my experiences, at least for now, I’d have to categorize as experimental rather than social. Mostly under the blanket of darkness and the dreary, surreal world of 3 AM suburban America. They were also a total adrenaline rush and a most EPIC opportunity to sharpen some people watching skills. I have had no issues yet. I am not trying to pass. I am enjoy being gracefully aloof. If you have not had the utter pleasure of seeing some the true sites along the highway of the Human experience? Occasion a large 24/7/365 store and be not shocked at what walks out from behind the next aisle! Fear not gentle citizen. Most of them are probably on medications! 🙂 I am probably not the most uncharacteristic patron they’ll see that night. I pretty much refuse to leave the house if my makeup isn’t spot on! I have found the people I interact with to be perfectly ordinary in they’re manner. It’s a good time to interact with the night shift. They are on the downhill side of the shift and looking forward to go home and just throwing it. It’s what they do. Pretty much every single one smiles and offers a greeting. Little parts of my Universe are working EXACTLY like they are supposed too! Seasons Greetings to all. Very Brightest Blessings for a HAPPY, Safe and Prosperous New Year.

    Liked by 2 people

  7. Really important post here! This is really an inspiring post. We all have to be open and patient enough to consider every thing fairly while taking any kind of action.

    Liked by 1 person

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