Getting Out and About: Top Tips

Chapter One

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. 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.

Chapter Two

Ok so you have read Chapter One and you are ready to go P A R T Y like a rock star. Just one problem you have nowhere to go! Not true, there are a multitude of places that will be only too happy to have you. What follows is a list of suggested places that are worth visiting dressed. Obviously it is heavily biassed by my geographic location (Johannesburg, South Africa) but hopefully it may spark some ideas for other people and provide some useful guiding principles as well.

The Basics
In my opinion it is best to avoid places where large numbers of single, young, heteronormative, cisgender men will gather. These people often drink alcohol and alcohol seldom encourages tolerance and a respect for diversity. They may identify you as trans and want to prove a point or worse one my be attracted to you, find out you are trans and feel a need to assert and (re)prove his manliness. These situations seldom end well for the transperson. You may be able to ‘handle yourself’ but wearing false nails, a wig, clothing that is unfamiliar and ‘fussy’ will reduce your ability to fight back. Heels will not only hamper your ability to fight (lack of balance, inability to kick etc) but they will also make it impossible to run away. Bottom line avoid conflict.
You want to be as comfortable as possible. This must be a fun experience for you. You therefore need to strike a balance between the familiar and anonymity. You do not want to go somewhere where you will be embarrassed if a waitress, proprietor etc recognises you. You also do not want to be constantly looking over your shoulder to see if friends, family or neighbours are there as well. Conversely if you go somewhere totally alien to you, you may feel awkward and uncomfortable in your surroundings. So if you are a beer and pretzels kind of guy, be careful about going to an upmarket cocktail or wine bar first time out (by all means build up to it if you wish but a more familiar environment may be better for your first time out).
Make sure you dress appropriately. If you wear that LBD with bling shoes and all the jewelry in your wardrobe to the supermarket, you will feel uncomfortable and you will draw attention to yourself. Attention the first timer can almost certainly do without.
Consider researching some LGBT friendly venues in your area. Make sure they are T friendly, not all LGB people are necessarily T friendly. You will almost certainly be surprised at how many palces are in fact LGBT friendly.
Consider going with a friend. I know this is not always possible for the first timer but if you have a close friend and ally you will almost certainly have more fun than on your own. Also something that struck me is that women (at least South African women) tend not to go anywhere on their own. You will blend in much better if you are with someone.
Finally, be prepared… It is a necessary requirement for Boy Scouts, Girl Guides and trans people!

Venues I have visited
Shopping Malls
I have been to Sandton City, Sandton Square, Rosebank Mall, Campus Square, Thrupps Illovo Centre, the V&A Waterfront and Cresta Mall. These are all malls in close proximity to my home (within a few kilometers) and are also where I shop normally. They are all relatively ‘liberal’ in character with a diverse crowd. Rosebank and Cresta in particular seem to have a fair number of lesbian and gay people who do not feel uncomfortable holding hands in these malls so I have assumed being trans is pretty safe too. They are relatively safe malls with security guards and a good reputation. I have eaten at restaurants, shopped for clothes, gifts and gift cards, watched movies and generally had a good time at these venues. I have had one or two less than ideal experiences but I have never been insulted, felt threatened or unsafe at any time. People have merely clocked me, and moved on. I have never been misgendered (in fact I have always been called “ma’am” or “ladies”)  either so well done to all the staff and patrons of these malls. I have never used the public toilets at these malls as I have never needed to. I do however prefer to avoid public toilets and go at home if at all possible. Some of the restaurants I have frequented include Doppio Zero, Piza e Vino (sic) and Mugg and Bean to name a few. I have shopped at a range of shops from Mr Price and PnP Clothing, through to Edgars, Woolworths and Stuttafords. I have not (yet) visited any boutiques.

I have been to see The Rocky Horror Picture Show at the Pieter Torien Theatre at Monte Casino and Swan Lake at the Civic Theatre. I was very impressed with the Monte Casino complex and pleasantly surprised at how accepting everyone was. The security personnel were professional and welcoming and did not misgender me and were happy for me to be searched by the female security guard. we had a very good meal at a restaurant in the casino complex and then went to the theatre. Here I had to use the public toilets and I had no problems using the ladies’ room. Although we were lucky in that we arrived early before there was a queue which did materialise whilst I was in the cubicle. I did not make use of the facilities in the Civic Theatre although my friend Jenny did. The staff at the Civic Theatre were less ‘cool’ than the staff at the Civic Theatre who were very eager to take photographs of the  ‘trannies in their midst’. But other than that all was good.
Our fellow theatre goers were very accepting and I felt no issues. Obviously Rocky Horror patrons are probably a fairly ‘cool’ bunch of people who would be happy to see the odd transgender person around. The ballet crowd  was different. It was almost exclusively female and even though we deliberately chose the later 8 pm show there were a lot of children (almost all girls) present. I was a little surprised by this as we have only ever taken our girls to the matinee shows. I simply did my best to blend in and not present too scary a prospect to the children. I do not recall any problems and I suspect that they were all too excited to pay much attention to me. Apart from that this was a good place to go dressed, perhaps a midweek 8 pm show would have less children and be a safer bet.

LGBT Friendly Spots
I have visited Trouble and Amuse on numerous occasions and have without fail had a fabulous time every time. Both venues are wonderfully welcoming of a diverse group of people. My wife has felt safe and welcome at all times as have I. I can heartily recommend these venues to anyone looking to get out and about in a safe and welcoming environment.
When in Cape Town I visited Beefcakes and I had a lovely time despite being on my own. The staff made sure everyone had a great time and that we partied hard, even though it was a weeknight. I have not been to the Johannesburg venues but I assume they work to the same formula. The cocktails were seriously good. No seriously the cocktails were good! And for those of you so inclined the waiters are all good looking young men, very friendly and witty and seem to know just how to give you a good experience. Also (again for those so inclined) their clothing is, shall we say, minimal… The pricing is however on the high side so be prepared to feel a lot poorer the next morning.
In Durban I stopped off at The Lounge. It was alright and maybe being midweek made it a bit underwhelming, but I did not feel welcome and I did not find the place very interesting. I left soon after arriving.
Amuse is very nice as the toilets are not segregated. Trouble has men’s and women’s toilets and I have always used the ladies’ room without incident.

Other Venues
In Kwa-Zulu Natal I have visited the promenade on the beach front in Umhlanga Rocks and the Moyo restaurant in Durban. I felt a little out of place on the beachfront but that was because I had dressed for a night out and had stopped off  at the beach before heading into Durban. I was thus rather overdressed. In truth as Durban is a rather relaxed city, I was overdressed for a night out so my outfit was a over the top for the beach. Such is life.

Places I Would Like to Visit
There are a number of places on my bucket list that I think will be good alternatives to the usual fare. Some of these are:
The Goodman GalleryMuseum Africathe Market TheatreGreensleeves Medieval KingdomLindfield HouseThe SaxonCirca Art GalleryLilliesleaf Farm, a concert at the Linder Auditorium, the Blues Roomthe Barnyard Theatre, the restaurants in 54 on Bath,  Stelle restaurant in Parkview, a spa for some pampering amongst other things.

I hope this has been useful. Feel free to contact me through my contact me page if you want more information.

Please excuse all the toilet stuff, but this can be a highly relevant piece of information when the need strikes!


Add yours →

  1. Thank you for sharing Daniella. For a non-trans person, your post has helped me understand your reality. You are beautiful.

    Liked by 1 person

  2. Thanks for the advice lovely lady.

    Can you please provide trans friendly bars/clubs in Gauteng?

    Liked by 1 person

    • Amuse Cafe in Linden is always a good spot. Open 6 nights a week. Chilled during the week with games evenings, poetry readings, quizzes etc and live bands and shows on weekends. There is a cover charge for most performances, but games nights etc are free. The kitchen is open every night and the cafe opens at 3. Full bar available.
      Trouble in Randpark Ridge is open on Wednesday and Saturday nights. Full bar with great cocktails and a kitchen (as yet untried). Good DJs and a fantastic vibe. Wednesdays are karaoke nights, Saturdays are party nights. Great dance floor with pool tables. Very nice place with trans people, gays, lesbians, straights, bi all welcome, all cool. They host a regular transgender party night every last Saturday of the month. No cover charge, ever.
      Babylon in Illovo is good by repute. I have never been.
      Beefcakes in Illovo and Bedfordview will be happy to have you… Always keen on trans people and you will feel and be safe. Beefcakes is ALWAYS a party… Even if there are only a few people there,the drag queens and waiters make sure everyone has a fantastic night.
      I have heard that there are a few other good spots, eg in Pretoria, but I myself have never ventured that far north dressed.
      I have also heard of a trans friendly gay bar on the east rand, but again I have never been…
      As far as restaurants, I have been to Mugg and Bean, Piza e Vino, Moyo etc as well as other restaurants in Sandton, Illovo and Monte Casino (sorry I forget the names) with no issues…
      Wherever I have been (with the exception of the restaurant at the Civic Theatre) the waiters have been professional and discreet with no problems ever. But the waiters at Beefcakes are by far the best. Highly professional, highly service oriented etc
      Perhaps I should draw up a more comprehensive list with reviews?
      Something to work on!
      Thanks for the idea.


  3. What a lovely post with all those useful tips! 🙂 Thanks, ~Sara

    Liked by 1 person

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