Lessons Learned: Part VI – Going Out


When it comes to be being somewhere on the Trans spectrum, there’s the question about going out. I’ve mentioned support groups and shopping previously, yet stepping out can be quite another thing, IMO. In some ways, getting outside feels like ability, confidence, style, and self acceptance coming together as one.

BTW, I don’t think you have to have a full house on those, and – dare I say – you decide when you’re ready. Maybe you’re still learning to dress or find your style, and your self acceptance isn’t there yet. But, so what? You want to get out there, you do that. You don’t need anyone’s permission (unless you’re borrowing the car 😉). Sometimes, you just have to take a deep breath and get out there.


Before we get to your manicured hand resting on the front door handle, let’s rev back a bit. Feel free to make that tape recorder gobbldigook noise if it helps. 🙂 Kids, you may need to ask your folks what a tape recorder is 😉

Thinking about this from a coaching angle, what’s your goal? Specifically, where are you headed? What might you need to get there? What might you need to have from a clothes/makeup point of view? What about when you arrive?

When it comes to planning things, having a rough idea of what you want is a good thing. IMO, try not to have a perfect day planned, because life isn’t like that. Instead, be flexible and don’t get caught up in the details too much. Equally, try not to have no plan either. That can lead to you driving around, not feeling that this stop is quite right, and you don’t get out at all. Cue much frustration and possibly disappointment.

So, having a place in mind can help you prepare mentally. It’s not a bad thing to have a backup plan either. That may be down to weather or a shift in the day you can go. That’s as true for what you might wear, when you might leave, and where your night go.

Let’s walk through a few examples. 🙂

Visiting a support group

There’s some truth, I feel, in the first step being the hardest. Yes, you are going to meet trans people like you and yes, these are likely to be strangers. Throw into the mix that your admitting to yourself that you are this way. Well, that’s a lot to take in! That’s before we get to the practicalities and the great of judgment on your abilities/outfit.

However, fear not, young padawans: a good support group is there to help. They’ll listen to you, not judge you, welcome you, and help you gain confidence in yourself. I think the socialisation in the real world helps let you see how others cope, do things, and it can help you find that this aspect of ourselves is completely fine. If you’re starting out, I can’t recommend going to a support group enough… and not just because I help run one 😉

Jokes aside, a group will have your back and having that place where you can be you is so important. It’s not fake flattery, BTW. If you ask for help about an outfit, expect kind and honest feedback.

What might you need? At one level, just your usual clothes and your courage. You don’t have to dress on your first visit. Looks of folk don’t and there’s no shame in that. Equally, you might have your first wig, a few outfits, and you’re learning around makeup. The key things here are courage and have the self belief that your doing your best right now. Sir, that may change, but be kind to yourself.

A walk in the park

A daytime trip means fitting in. Well, it does if you don’t want to draw attention to yourself. I’m not talking about passing, I’m talking about looking like you belong. If people think you’re part of the everyday, they are more likely to look by you, and you can go about your business.

If the park is busy, this may play to your advantage. You may be lost in the numbers, even if this gives you the willies (aka the heebie-jeebies / the fear).

But back to blending in. Jeans, fiat shoes, and a casual cost will be okay. The key thing is seeing what other women (or men) of your age wear where there. Oh, taking the dog with you? When did you last see a dog walker in their best heeled boots and cute skirt? If you want the latter, leave the former. 🙂

If the park is more urban, you might be able to use the On the Way to the Office vibe or Just Out for Lunch schtick. That may let you switch the jeans and shoes to a skirt and heels. Just remember you’re going for office style, do leave the stilettos in the cupboard this time.

A trip to the shops

I think this depends on where you are headed. Popping out to a distant village or out of town retail park will mean you’ll see less people, but perhaps not gain the anonymity of city crowds.

Out of town is good to help gain confidence. Parking should be fairly easy and you can easily nip back to the car to drop off any purchases.

If you’re heading to a big town, do plan your route and maybe do a bit of research on the gap between car park and shops. When is rush hour, the school run, or other big event that might effect the traffic? Also, re the time of day and location: this will effect your blending in choice. Leave the high glam stuff behind for now and consider what shoppers your age will have on. Office level or smartish can work well here, just as can jeans plus cute top. Heels are lovely, yes, just make sure you can walk in them and that they are broken in before any reasonable walking is attempted. You might find a boot, flat pump, or Mary Jane more forgiving.

If you are planning on trying anything on, do think about how off-and-on-able your outfit it. Tights: nude, as they go with everything, or black opaques? Which works for the season and shopping? Try not to forget a hairbrush and possibly a lippy too.

Remember to be polite and have confidence that you belong. You are valid and you’ve every right to be out enjoying yourself. Scuttling from car to shop will make you stand out more, so try to fake it till you make it.

A night out

If we stay with pub, club, or restaurant; each of those venues has its own dress code.

Some pubs, like some restaurants, are very casual, while some are quite fancy. It’s that delicate line of being neither over dressed not underdressed. If meeting with friends, ask their advice if you’ve not been. Failing that maybe check the place out beforehand if that’s doable.

On the night itself, think about travel and the gap between venue and parking. Will you need a coat or maybe a taxi? If it’s windy week you need a hairbrush or an umbrella of its raining? Do you have a bag and a purse for your keys and cards? How will you pay for the meal? Will you split the bill? You may need cash for that. As much as shapewear can be our friend, how will you fair if sat down or eating? Perhaps something to practice.

As to clubbing, shoes you can dance in (if you’re a dancer 🙂), an outfit that you feel works for you (conference), and that’ll let you in the venue. Oh, you might need ID to get into some clubs, so check in advance. A set of ear plugs might not be a bad idea as some sound systems can be very loud.

If you’re going with friends, having someone to watch your handbag is awesome. If not, consider how you keep your card and money safe on you. Oh, do be careful when drinking. Not just the amount, but don’t leave a drink unattended and come back to it, that may not be safe.

What else?

There’s more than those few examples – like long distance travel, staying overnight, etc. – but let’s go with the basics.

You’ll have noticed I’ve written a few times about picking the outfit that will blend in. It’s not about dressing down, but I do think it’s about wearing clothes that help you fit in. If you’re more a skirt and heels person, that’s fine: adjust your day out to fit. Equally, if you love jeans and a cute top, own that look and enjoy your day. There’s plenty of ways to be. Try not to worry about folk looking at you, chances are they are stuck in their own head, thinking about their own little world.

If you are driving anywhere, make sure your car is fuelled and – this might seem a bit daft – know where you’re going. What I mean is, have an idea of which town you’re headed to. This can avoid you driving around, looking for the perfect spot to stop. Do that thinking well before you are dressed and out. When you’re out, drive carefully, sensibly, and enjoy the journey to your destination. There’s no need to take risks as you can always come back another day.

If you’re taking public transport, don’t forget your money and know your route there and back. If you can, try to avoid complicated routes, unless you like riding around all day 🙂 Oh, keep an eye on the time, as spending an hour at the bus stop isn’t a lot of fun. If you’re male to female, do think about your personal safety. It’s not that buses aren’t safe: just try to avoid being the lone woman waiting at a dark corner for the bus. There’s nothing wrong with waiting in a nearby café, or mixing your journey up with a taxi ride.

With all of that our of the way, we can fast forward to you opening that front door and taking a step outside. Hear the sound of your shoes as you walk, enjoy the sun in your face, and possibly the breeze on your legs. You’ve got this. Go have fun. ❤️

L x


  1. One piece of useful advice when venturing out for the first or first few times is to scout your route first. If you can’t dress at home, or can’t be seen leaving or entering the house while dressed then make a note of the locations of any gender neutral public toilets which might find in market squares, parks, car parks, or (more rarely) shopping centres. Churches, if open, may be good too. Check if they have enough space to change comfortably, and ideally enough lighting and a mirror for makeup. If not, remember to take a good sized mirror of your own. Always pack a bag of makeup wipes and a spare pair of flats, especially if you’re not used to walking any distance in heels. (Walking outside is a lot different to strutting your living room).
    Make sure your wig is comfortable and secure and will stay that way. (One trick I learned is to sew the top of of a holdup stocking round the inside the headband so it grips and holds securely.)
    Dress comfortably.
    I agree with Lynn about groups, and not feeling you have to go dressed first time. I didn’t dress until my fifth or sixth meeting, and when Susie finally appeared she was greeted with smiles and hugs all round (bring back those pre-Covid days). By the end of the evening I was and happy and comfortable to wander down to bar on my own to get the next round of drinks in.

    1. Sage advice, Susie. Thanks for sharing. Knowing the area is a good idea. See also, “know your exits” 😁 Having a set of wipes certainly helps. That and clothes you can change into quickly, or pop over your outfit until you get home safely.

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