I don’t profess to be an expert here. Far from it, in fact, as every single contributor here has far more experience of being in the outside world than me. If I have any advantage over them, it’s the fact that my memories of stepping out for the first time are more recent than theirs as my trips out only started in November 2020. In fact, in my closeted days, I would feel more than a hint of envy at those who had the guts to go out into the world in their feminine finest, never for one moment thinking that one day it would be me. In fact, I’d read Kandi’s posts each day and think ‘I could never do that’. And yet in the space of five years, I’ve evolved from someone taking their first faltering steps to someone who no longer fears interactions with others and happily does anything and everything in her feminine persona.
All of this clearly didn’t happen overnight and, like the preceding two posts in this series, this is very much aimed at readers who are in the closet, wanting to spread their feminine wings beyond the confines of their house but remain very apprehensive about the whole idea. To bring this series to a close, I’d like to offer up a five point plan put together from my own experiences which has been instrumental in getting me to where I am today.
1. See the world through ‘her’ eyes.
As a closeted CDer, I used to deal with my urges at home with the curtains tightly closed. No one could see in and I couldn’t see out. It gave me the sense of security that I desperately needed but as time went on, I realised that if I was going to go out, ‘she’ needed to inhabit the same world that ‘he’ did. So one day, I got myself dressed up and went to the front door, pulled back the privacy curtain and looked through it into the outside world – the world that ‘he’ routinely occupied but ‘she’ had never dared see, never mind set foot in.
Unsurprisingly, the world outside my house looked exactly the same through ‘her’ eyes as it did through ‘his’ and it provided a much needed preview of what to expect when I finally did take a deep breath and open the door just two days later. Sportsmen and sportswomen use visualisation a lot – imagining themselves winning a race, achieving a record breaking jump or negotiating a challenging course – so it’s no surprise that it helps in our world too. By seeing the world through ‘her’ eyes and imagining myself walking in it, it became much easier when the time finally came.
2. Be the best you can possibly be.
Being out in the world requires confidence in yourself and there’s no better source of that confidence than looking in the mirror and being happy with the person smiling back. Inevitably, that means hair and makeup for us. It’s very easy to make a complete hash of makeup application, particularly if you don’t have a decent understanding of what goes where and how it should be applied. If ever something epitomises the expression ‘less is more’, it’s makeup application where overuse of the blusher and lipstick can quickly make you look like Ronald McDonald.
Fortunately, help is at hand in the form of YouTube videos and it’s reasonably easy to get the basics nailed down fairly quickly. What helped me was understanding that it wasn’t a case of putting on makeup but, rather applying individual elements such as foundation, eyeliner and lipstick etc. Some things are easy – lipstick being the obvious one as most of us have watched female relatives apply it – and others are a lot more difficult to do well. A particular challenge I faced was eyeshadow, not least as I can’t wear my glasses to apply it and being very long sighted, I found it difficult to focus on where the brush was actually going. It’s also good to notice how women approach makeup application – I still remember a woman I saw sitting opposite me on the train whose eyeshadow was just a single shade, quite dark and just on the lids. It looked good, was simple and gave me inspiration for something I could replicate on myself.
And if you mess up, don’t be afraid to wipe it off and have another go. Brows are a particular bugbear of mine and it normally takes two or three tries before I’m happy. I just wipe off the mess, touch up the foundation and try again till I’m happy. And false eyelashes became a lot easier when I invested in proper lash glue rather than trying to improvise (using a tip I got from the internet which, for avoidance of doubt, did NOT involve superglue!).
And just a note about hair. A decent wig is a game changer – many of us, including me, start with cheap wigs from Amazon and the like but it doesn’t cost the earth to get one that’s of far better quality – my Noriko Carrie cost under £100. There are a range of online sellers with good inventory and regular special offers but spending a bit more at bricks and mortar stores can pay dividends as the wig will be properly styled when it is sold to you. It’s also an opportunity to try before you buy because, sadly, the wig that looks amazing on a model may not deliver on its promises in reality.
3. Review your wardrobe.
Like many, I started with a bodycon dress and stiletto courts/pumps. It’s a style I still love but one that few women wear these days other than in high end offices and where evening elegance is required. A walk down the local high street gives more than enough evidence of its more or less complete absence from women’s daily wear wardrobes. I learned the hard way that being overdressed for the environment does not make being out and about a particularly pleasurable experience and realised I needed a rethink.
In my post ‘One Giant Leap – The Capsule Has Landed’ (https://kandis-land.com/one-giant-leap-the-capsule-has-landed/), I extolled the virtues of ‘capsule wardrobes’ – a small collection of clothes, shoes and accessories that can be mixed and matched into outfits suitable for a range of situations and that’s been transformative for me. Whilst my ‘stash’ has evolved more through good luck than good planning, I’m now able to put together a range of outfits from very casual to formal and no longer feel out of place wherever I happen to be. And that has proved to be a real confidence booster.
Furthermore, as you gain in confidence, planning an outfit for a particular outing is part of the fun.
4. Get shoes that fit.
In the same way that I learned the hard way about the perils of being overdressed, I was taught a similar lesson about shoes. My early outings were always characterised by extreme discomfort in my feet after walking even a few yards. I initially thought it must be the heel height – I do rather like my heels, particularly stilettos – and whilst I was happy to make some compromises with my outfits, ditching the heels was not an option as far as I was concerned. I tried lower heels which helped but my opportunities to go out are limited and when I do go out, I like to feel good and heels are a key factor in that.
In the UK, the upper limit of most women’s styles tends to be size 8 and I can get my feet into most shoes this size. However, I normally take a UK9 and I wondered whether trying to find women’s shoes in a similar size would help. It wasn’t easy but I finally found a pair of reasonably priced (i.e. cheap!) heeled boots in that size and decided to give them a go. It was like walking on air compared to what I’d previously been used to.
They weren’t particularly stylish though so I looked around for footwear more in keeping with my preferred style and found a pair of knee high boots on Amazon and the most gorgeous pair of pointed stiletto ankle boots available click & collect locally, both in size 9. The heels on each are in the range 3”-4” but I have managed to walk over a mile in both without problems.
It’s much easier to feel confident when I have no worries about my feet!
5. Find a friend.
I prefer to fly solo on my outings. The more of us that congregate in one place, the more likely it is that we’ll draw attention to ourselves and I prefer to blend in rather than stand out. However, I was lucky enough to be able to be accompanied by another CDer who had none of the hangups I did at a critical stage in my evolution.
Any CDer who goes into the outside world will be only too happy to reassure you that you’ll be fine but that’s not easy to believe when the mere prospect of being confronted by humanity fills you with terror. When an online friend suggested meeting IRL, I tried to decline saying I wasn’t ready but she wouldn’t take no for an answer and every objection I raised was calmly dismantled. In the end, I just gave up and agreed.
What I learned first hand on that afternoon which was just afternoon tea and a chat in a hotel was that people genuinely don’t care these days. The waitress took our order, checked that everything was OK and treated us no differently than I would expect to be treated if I had been dressed in my normal garb. Another member of staff asked us how we were when we left the restaurant and everything just felt so normal. Just a few weeks later, I was in a shop queueing up to pay for tissues and then a café for tea and a pastry. Maybe in time I would have done those things without the baptism of fire with the other CDer but there’s nothing better than being shown that there really isn’t anything to be worried about.
Bonus tip – be her
The preceding five tips are designed to help you make your first tentative steps out. This one is really only viable when you’re used to being out.
Because of limitations at home, these days I usually need a night alone in a hotel to be able to unleash the inner woman. But this normally means booking the hotel in my legal name, turning up as ‘him’ then getting changed and apprehensively walking past the receptionist hoping that they won’t connect female me with the guy who checked in an hour or so earlier. I don’t operate under any illusions that I ‘pass’ but, equally, I don’t want to be seen as a fetishistic CDer up to no good on a night away!
And so for my most recent night away, I booked the hotel in the name of Ms Amanda Johnson and announced myself as her when I arrived. I have never felt more relaxed in this persona and for the whole time, felt that female me had the right to be there. I was proud to be me and if the staff wanted to talk about me behind my back, I was the ‘transgender person’ or something similar, not ‘that scruffy guy who checked in an hour ago’! You can read more about my adventures in my ‘Living The Dream’ series of posts.
And I’m happy to be referred to as a transgender person or even a crossdresser. Because being seen as one of us means that I can be an ambassador for our community and hopefully represent us in a positive way.
-o-O-o-
There’s something quite wonderful when we finally fully discover ourselves and find what we may have spent years, if not decades, looking for. Being in the outside world is a logical step in our journey but it’s not always easy, either plucking up the courage to do it or when we finally make that step and feel uncomfortable in our surroundings. And what to me is second nature nowadays was inconceivable when I started trying to accept this side of myself.
Perhaps the biggest lesson I’ve learned is to stop worrying about things I can’t control and focus on the things that I can. If someone wants to point and smirk, there’s nothing I can do to stop them. But I can put my heart and soul into presenting myself in a way that society expects and, in so doing, those points and smirks may well not happen. Most of all, though, it’s about enjoying the ride because even the smallest sign of acceptance – a smile or a door held open – makes it all worthwhile.









13 Responses
Having been going out for years, i find that once i put my ‘hair’ on its like the flick of a switch and mentally the balance tips from male to female. Although i have anxiety issues i am rarely anxious as Helen – the worrying tips you mention i have to apply more when presenting male!
Some tips from my experiences
Wigs – not just quality but well cared for. I’ve had loads over the years but now find using Ellen Wille wig shampoo and balm helps wigs last longer, and i’m wearing them most days. Its around £20 on Amazon, one bottle of each.
Shoes – i am a UK 8 but had issues with cellulitis that has left my left foot quite swollen on top. I buy most of my shoes in Shoezone, the Lilley and Skinner range goes up to 9, and i have lots of their flatties, i’m wearing some pretty wedges from there today. Next also say they go to 9. Yours Shops go up to 10 in boots (also Evans online) but i still can’t get into them. Yours do lovely larger size jewellery too.
Finally, for our US sisters, male me was in New York a couple of weeks ago, and a Primark was opening on 34 St opposite Macys – great shop for fast and cheap fashion.
Helen, thank you for sharing your thoughts and great advice.
Shoezone and Next are great places for us in the UK – I’ve had size 9s from both and it was a game changer for me after years of just about being able to cram my feet into 8s. What I never realised until I had shoes that fitted was how much more enjoyable being out and about was as a result.
Thank you for the wig advice too. I have to confess that I abuse mine more out of necessity (because it has to be hidden away) and it’s well overdue for a bit of TLC.
Amanda,
I have to highlight “shoes that fit”. When I was trying on my first high heels in the clearance isle of a DSW, a woman also trying on shoes near me told me “life’s too short for shoes that hurt.” Very wise words that I have lived by for over a decade. I wear high heels all the time when out, somethings for 16 hours straight. If you are paying attention to the pain in your feet, you are eliminating your enjoyment of being out while also drawing attention to yourself.
Cali, great advice thanks. Before I discovered that fabulous shoes were available in UK9 (US11) outings only lasted a few minutes before my feet were killing me in my size 8s. I always assumed it was the heel height and going for a lower heel did help a bit. But since I found size 9s, I’ve walked over a mile in 3″ heels on several occasions and enjoyed the experience too.
Another great source of larger size women’s shoes in elegant styles relevant to both sides of The Atlantic is Amazon,
Mandy,
I’m size 10(us)and somethings size 11. I have a high arch and narrow heels, so my feet fit women shoes and not men’s. I search many sites looking for shoes. Very disappointed that I can’t find the shoes in brick and mortar stores since I return 9 out of every 10 shoes I order on-line and none of the shoes I try on first.
The whole sizing thing is a minefield. In my normal life, I take a UK9 which is apparently equivalent to a UK8.5 women’s (not that these are easy to find) which, according to the conversion tables I found online, is a US 9.5 men’s and US 10.5 women’s – so a women’s size 9 in the UK is larger than a men’s size 9 but, in the US, a women’s 9 is smaller than a men’s 9.
I did buy what I thought was a pair of women’s size 9s from Amazon but was quite shocked to see 11 stamped on the sole before realising that despite this being the UK, the shoes were seemingly imported from, or at least produced for, the US. They were also a bit too big because my size is actually equivalent to a women’s UK8.5/US10.5!
To make matters worse, here we also have to contend with European sizes which, for my size is 43.5 men’s or 41 women’s.
All of that, of course, is incidental if shops don’t stock large sizes. One chain here – Deichmann is a crossdresser’s dream. The shoes are displayed in their boxes so no picking up the display shoe and asking the assistant if they have it in your size but there’s one big problem – practically all of the heels they sell stop at size 7. It’s particularly distressing as many of their styles are to die for (which, of course, does not mean that I want my feet to kill me!).
As the other correspondants state getting the right shoes is a key element in going out and being comfortable. High heels look great in your mirror in your apartment but can be a torture when out and having to negotiate city centres with cobble stone, tram tracks and broken paving.
I also have problems with sizing as in Belgium womens shoes usual only go up to size 41, so I tend to buy shoes I. The Netherland and UK which offer sizes 42 and 43. I have a couple of kitten heel shoes and some ankle and knee length boots which give me a range of options.
I then to go for a block heel boot if I know I will have a fair bit of walking – our town centres are notorious unfriendly to heels, and more elegant heels if we are going somewhere more refined and the walking will be on even surfaces
Tanja, thank you for giving us the European perspective!
I have to confess to a little envy at this point – I’ve been to some lovely towns in Belgium and the surrounding countries but, sadly, the cobblestones and tram tracks in many British towns were replaced by concrete (as were most of the buildings) in the mid 20th century. I can understand the problems with heels, though, although we do have our fair share of broken paving here too.
I just had a look at the Belgian Amazon site and the selection of larger size shoes seems far wider than on Amazon UK. Obviously buying online can be a bit hit and miss but, as you say, our options reduce significantly as the size increases.
Amanda,
I also envy you as in the UK, Marks & Spenser have some really nice shoes in larger sizes, that are well made and at reasonable prices.
I have some boots I purchased online but tend to pick up shoes from boxed up stores like Van Haren and hope they fit or get in the sales in a larger store when in Eindhoven or Rotterdam, and they alway seem to have the larger sizes. There is a very famous shoe store for crossdressers in the Cool District of Rotterdam, but I find them expensive and a bit ‘draggy’ – definitely not what to wear to blend in 🙂
Where Marks and Spencer really excel is in larger size clothing. I’m not particularly large but what I often find is that clothes that should fit me according to the shop’s sizing guide are still too small. M&S, though, usually have a full range of sizes from the most petite to things that are far too big for me.
At one time we also had Evans which catered for the larger woman. Their stores have gone now (although their clothes are available via ‘Yours’) but the mother of one of our staff members worked in one of the Evans shops about a decade ago and said that she was always seeing crossdressers or guys ‘shopping for my wife who’s about the same size as me’!
Amanda ,
To take up Helen’s point about good quality wigs and their aftercare . Obviously I wear one everyday so I had to spend slightly more and buy monocaps ( because they’re light weight and breathable ) usually from Valentine Wigs , at the moment I wear a Noriko Ryan in creamy toffee R . No matter how much you spend they all have a limited life most don’t expect them to last more than a year , I push mine to about 18 months to two years . I’ve tried most shampoos and conditioners and still find Johnson’s baby shampoo and a Loreal conditioner works fine I also style them with rollers and let them dry naturally over night once a week . Nowdays if I’m spending time away I will take two which means I can wear one in the day and slip the second on for evenings , this allow me to rinse the other through if needed .
I agree shoes are a nightmare , from very early on I realised you have to try them on , which can be fun in male mode . I miss Brantano as they usually stocked up to a UK size 9 , I’m lucky taking a size 8 . Women’s feet are getting bigger , very often Matalan sell out of size 8s first . I still regularly check out charity shops , the point being someone else has worn them in , most of my boots were found that way . For everyday easy wear shoes I often buy Cotton Traders , they’re always a wide fit and have a nice sized heel , just today I’ve been to my art group and then done my chores around town in some pretty CT sandals , to go with a cream summer skirt and yellow/gold Tshirt .
Teresa, thank you for the advice.
As regards shoes, the only saving grace is that a women’s size 8 is bigger than a men’s which probably explains how I can wear the former but not the latter. That’s not to say that they’re comfortable for anything more than a very short walk and anything more than a low heel just adds to the discomfort. Once I found 9s, everything changed but, unfortunately size 9 shoes are too big and are hard to keep on – I tried those sticky things inside the heel but without much success. Boots though are a different story as the design means they don’t come off. Ideally I think I need an 8.5 but they’re even rarer than 9s.
My wig is well overdue for a bit of TLC – the difficulty is keeping it hidden while it dries but I definitely need to do something with it.
Amanda,
I do wonder what the hotel staff or cabin steward thought when they caught sight of the wig stands when cleaning my room . We shouldn’t forget that many of the wig outlets supply women for various reasons so it wouldn’t be the first time they have seen a wig on a stand while cleaning .
When washed in tepid water they should be allowed to dry naturally , I soon discovered even a warm hair dryer can cause the wig fibres to shed .