Shop hopping

It’s been ages since I got new clothes. I think I’ve probably got as much as I want in my wardrobe now. Maybe I’ve found my ‘look’ and I’m happy with it? Or maybe I’m not going out as much as I used to, and now I can just re-use my old favourites? (It’s always a huge relief to find I can still fit into a dress I bought four or five years ago…)

When I first started building up my wardrobe (after deciding what clothes and footwear to go for), I just went with my girlfriend and built up a modest stock of cheap underwear and basic skirts and tops from local shops. For solo shopping trips, I’d go to shops on the other side of town where there was no chance of bumping into anyone I knew. (The easiest trips were to fancy dress shops – it’s not like you have to explain yourself…)

I'm so bad at snooker, I can't even hold the cue properly...

One of my earliest and favourite purchases.

I’ve always been determined to work within a strict budget – so a large part of Twist’s wardrobe comes from second-hand charity shops. These tend to be slightly opportunistic or impulsive purchases – I’ll see something on a mannequin and think “Hell, yes!” and (assuming it’s about the right size) buy it because if it doesn’t work out, at least I haven’t blown vast amounts of money on it. More often than not, I have a ‘look’ in mind and scout around seeing if there’s anything that comes vaguely close to it.

You never know quite who’s going to be behind the till. On an early venture, I spied a slinky dress in a window that was perfect, and went inside. It was packed with little old ladies rummaging through winter coats, but I apologised my way through the crowd to the cashier and told her I wanted to buy That Dress in the window. She had a mischievous look in her eye.

She opened up the display and shouted back to me, “IS THIS THE DRESS YOU WANT, SIR?”

I was damned if I was going to let her try to out-sass me or try to make me feel foolish, even in guy mode. So I shouted back with a cheery smile and a thumbs-up.


I don’t think anyone else in the shop was paying the slightest attention to either of us.

"We're not flying; we're falling with style!"

The zipper on this dress was… eh, ‘flying low’…

On another occasion I was looking for a vintage 60’s-style dress for a photoshoot (the one in the old fashioned airliner; apart from having to avoid a children’s party, that shoot passed without incident and the photos can be seen sprinkled throughout the gallery).

I found exactly what I was after in a charity shop in a very genteel, prim, proper part of town. The sweet little old lady (Edinburgh’s second-hand shops contain no other sort) behind the till struck me as the kind of woman who was probably schooled by Miss Jean Brodie.

She rung it up and said, “There you are sir, one ladies’ dress.”

And I got to use the Eddie Izzard line, “It’s not a ladies’ dress – it’s mine!”

I thanked her and packed it into my bag. She just blinked, speechless. I think I was a bit too modern for her tastes.

(It turned out the dress was too small, so I had to figure out how to pose without showing the gaping zipper at the side.)

When it comes to charity shops, I go for the secular ones – health, animal welfare, and social support. The only shop I refuse to donate to or buy from on principle is the Salvation Army (because it’s just not a very nice organisation).

castle gardens

Splashing out…

I have splashed out occasionally. On a trip to Orlando five years back, we got an idea of the political divide between two stores.

The first was an upmarket dress shop; lots of stuff I’d love to have tried out, but the sales assistant was a middle-aged woman with big hair who struck me as the type who was Afraid Of Change and would vote accordingly.

She asked my girlfriend if she was interested in anything.

“Nah, we’re here for him.”

The saleslady laughed politely.

“No, seriously, it’s for me. I like to rock a dress from time to time,” I told her.

“Well, you don’t seem the type!”

“Don’t I? Damn. I’ll have to try harder.”

Uncertainty crossed her eyes.

“Let me know if you see anything you like,” she told my girlfriend, and left us alone. We departed about five seconds afterwards.

Instead, I found a couple of slinky purple dresses – one sparkly, one not – in American Apparel. I’m guessing it was a couple of college kids running the shop, and they were totally fine with me buying dresses. Kids today, huh?

Sing when you're whinnying?

Got milk?

Personally, I try not to buy stuff online – I like to actually see what the hell I’m getting first – but last year I succumbed to the temptations of a sale at Black Milk. Their range is of the tight’n’stretchy variety, so It takes a bit of dietary punishment to wear them confidently. I could go nuts clicking on purchases, but then a little voice has to restrain me: just when, precisely, do intend to wear a PVC skater dress?

Sometimes, the idea of wearing something is far better than the reality of it.



And a one, and a two…

Gender-neutral toilets already exist. Every home has one, (unless there are two and the ladies and gents of the house retire to different ones?). And anyone classed as ‘disabled’ might also feel that they’ve been de-sexed as well, since the wheelchair sign applies to mode of transport rather than genitalia.

Even so, when I go out cross-dressed I plan ahead a bit. I try not to eat or drink too much beforehand, to minimise any trips to the smallest room in the building. It can also depend on what I’ve chosen to wear for the evening; sometimes there might be a bit of structural engineering works to undo before I can -you know- do anything.

I like to have some idea of where I’m going – ideally, does it have a disabled toilet? I can justify this on the grounds that when cross-dressed, biology and presentation cancel each other out, making me gender-neutral. Also, if I can’t run in heels, breathe in a corset, or eat big meals (it might wreck my makeup), I’ll pretend that they all count as a disabilities.

Sometimes, I don’t have that option. As always, I think I have it easier than anyone who’s transitioning (and at the mercy of short-sighted local laws when caught short). I identify as a guy; I’m a bloke; a dude (but I refuse to think of myself as ‘manly’); it’s just that I’m wearing a skirt. So I’ll use the gents’ toilets, thank you.

These situations are where I get all brazen (I won’t say ‘cocky’…). At a restaurant with friends, I went to the gents to fix my lipstick after the meal. A guy walked in after me and immediately went into Embarrassed Brit Mode (imagine a young Hugh Grant doing his flustered-and-stuttering routine).

Gent: “Oh, christ! I’m terribly sorry! I thought this was the gents!”

Me: “Nah, you’re okay; this is the gents. I’m just doing my makeup.”

Gent: “Um… um… …” [leaves, unrelieved]

I don’t know if this would work for anyone else – there are some places I wouldn’t even dare – but acting like what you’re doing is nothing out of the ordinary is a great way to convince people that it really isn’t anything out of the ordinary.

Mind you, there was another meal where I attended in a red Star Trek dress, and it took about thirty seconds to convince the diners who came in after me that they were actually in the right toilet. I think the trick is to take advantage of the awkwardness and be proactive with it. If someone else feels awkward, that doesn’t mean you have to as well. You can’t show weakness when you look fabulous.

On the other hand, if I’m in a pub setting where I haven’t been before, and there isn’t a disabled toilet, I can either nurse my drinks very slowly, or rely on the goodwill of female friends to check the coast is clear in the ladies’ toilets (that’s happened before as well).

If any readers live in a jurisdiction where toilets have somehow become sexualised, I dearly hope things change soon. Apart from death and taxes, needing to have a pee is something else none of us can escape from, and I see no reason why this should be made difficult for anyone.

The best solution I’ve seen is this:


“She told me to walk this wayyyyy…”

One thing I wondered about when I started cross-dressing was what the hell I was going to put on my feet. It wasn’t long before I realised why certain women go nuts when it comes to footwear.

Shoo away
The first thing a cross-dresser should know is that you don’t have to wear heels. Really; you don’t. Take a look at a busy street in the middle of the day and see if you can figure out the proportion of women wearing heels. It’s pretty damn low. Heels are uncomfortable, impractical, and unsuitable for a variety of surfaces and gradients.

If you’re starting out, it’s a better idea to figure out what style of footwear goes with the rest of the clothes you’re acquiring (a quick, handy guide can be found here). Does the colour match your outfit? Or will you take the easy option and just go with all-black footwear?

How much into crossdressing do you want to go? Do you want to have a different pair of shoes for every outfit, or do you just want a few different styles that will cover all possibilities? (I ended up with just three pairs of boots -one flat, one with stiletto heels and one with insane four-inch heels- and two pairs of heeled shoes.)

It’s also worth considering where you’re going and how much walking or standing about you’re going to do. I can attest that walking on cobbles in heels is a bit of a sod, and that if you’re going to climb eight storeys of stairs in stilletto heels, you’re going to have a bad time. The longest I spent in heels was 14 hours, and I regretted it for days afterwards. So, if you want to try to look glamorous, go ahead; just be aware that you’ll pay for it…

These boots were made for walkin’
Even with only fifteen dots on a black background as a guide, it’s possible for us to identify the differences between a ‘male’ and ‘female’ gait. So, if you really wanted to present yourself as ‘feminine’ as possible, you’d have to learn how to alter the way you walk. This doesn’t mean walking like a runway model, but it could mean making some subtle adjustments to your, pace, stride and posture. (If you want to play about with different walk styles from the comfort of your chair, I strongly recommend giving the BioMotionLab walk simulator a go.)

Brought to heel
Personally, I think there’s something oddly empowering about walking around in heels. There’s the gain in height, the loud clack (or scrape) as they hit the ground, and the shift in posture they bring. And if you can walk in heels confidently, you’ll earn minor kudos. Bear in mind that men are heavier than women, so heels may not support your weight. And, like most things in life, don’t overdo it.

One tip I was given for learning to walk in heels was to do vacuuming around the house in them; in the process, your feet and ankle joints will go through a full range of motion in them, helping you to acclimatise. And you’ll have clean floors, too, so hey – that’s a bonus. My girlfriend once returned to find me doing this, and you can imagine her surprise. Not that I was wearing heels; that I was doing the vacuuming.

If you’re at all unsure, film yourself and see how you look. Try to find something that feels comfortable; if your gait is natural and easy, you won’t draw attention to yourself in a bad way.

Sometimes, though, you just need to make a complete tit of yourself in public in order to learn to do better the next time. This is me walking in smooth-soled heels on the polished, curving deck of a boat:


Assuming you’re not wanting to stay at home and cross-dress quietly, it’s usually a good idea to figure out what sort of ‘look’ suits you.

Tarting yourself up before going out isn’t really an impulsive, snap decision to make. After all, you’ve been practising putting on makeup and choosing what to wear, but does it suit you? Are you at all worried that the skirt is too short? Or that you look like a guy in a dress rather than someone more ambiguous or even feminine? Will people stop and stare and ask you, “Dude… what the fuck?

There’s a lot you can miss looking in the mirror, so you can give yourself permission to take a selfie. Really, it’s OK. Take pictures of yourself standing, sitting, walking about even. The main thing is, when you look at the pictures or movie clips, would you say to yourself, “Dude, what the fuck?” If you would, if you have a niggle in the back of your mind that maybe you shouldn’t go out looking like that, then don’t. Only head out once you’re wearing something you feel works for you. Put your mind at ease as much as possible. If something doesn’t look good, try to figure out why.

For my part, it helped me reject a whole load of skirts, tops and dresses I got from charity shops to see if I could make them work. The one on the left, below, is from my not-quite-ready-to-go-public days. I wore it for a few selfies before realising I hated the colour and style – and that just because something looks good on a mannequin, it doesn’t mean it’d look good on me; picking up basic stuff like this took a bit of trial and error. As for the one on the right, I figured out very quickly that skirt length is important when you’re sitting down…

Figuring out what not to wear is just as important as figuring out what to wear...

Figuring out what not to wear is just as important as figuring out what to wear…

Looking at selfies also made me hypercritical about my makeup and posture and how much fat I should lose. But it was worth it; by the time I did go out, I was as confident about my appearance as I could be without getting independent feedback.

Now, I’m a vain, loudmouth attention-slut (when I’m in a good mood and things are going well), so I’ve had pictures taken in all sorts of places just so I can have a record of different looks I’ve tried. A lot of these were done really early on summer mornings, or in quiet locations, or sometimes both. The main thing is, there was plenty of time and space to get poses, backgrounds and angles right (or at least, ‘right’ enough, given I was freezing my arse off and didn’t want to completely exhaust my girlfriend’s patience).

The trouble is, taking photos in public can cause problems when there are other people about. If you’re wanting to try something cute, having onlookers can be a bit inhibiting. Worse than that, if you’re on private property (cinemas, shops and the like count as this), people can ask you to leave, which is awkward. Strictly speaking, you need permission to take photos in a shopping centre (for example) because it’s private property. In practice, you can take photos until you’re asked to stop (and security guards *will* ask, because it’s an easy way to demonstrate they’re doing their jobs). They can ask you to leave, or escort you out, but they can’t take your camera, ask to see or delete photos or detain you. You can take photos from the pavement (but not the car park), though.

Personally, I think it’s worth taking pictures when you’re out cross-dressed. Give yourself something to look back on. Give yourself something so you can see how your ‘look’ has developed from the early days. Give yourself a record of something you’ve never done before!

Boldly going where no man... uh... never mind.

Boldly going where no man… uh… never mind.

Going Out…

Following on from the previous post, once you’ve ‘come out’ as a crossdresser, are you going to stay hidden at home, or will you dare to venture out in public?

It can be a nerve-wracking thought, given that you’ve no idea how people will react (depending on location, you may have more or less reason to fear hostile or mocking responses). Before going out for the first time, make sure you’re as presentable as you think you can be. I wanted to blend in rather than stand out, so no fancy dress, no party wigs, no trying to look sexy – just normal street clothes.

I went for a walk around the block with my girlfriend at about 10pm (it was a safe neighbourhood), just to get accustomed to the idea of being all dressed up and out in public. It was dark and there were very few people about, but I could at least gauge their reactions and be confident that if things went wrong, they wouldn’t create a scene and I was just 5 minutes from safety (I wore flat knee-high boots in case I felt the need to run).

All these preparations and worries and… nothing happened. We walked about for ten minutes. I think we passed a couple of dozen people at most. There were maybe a couple of girls who did a double take, but nobody paid me any attention. I was a bit miffed. Relieved, but miffed. But it was a start. We went out again to watch New Year fireworks (bit awkward; strangers wishing me a happy new year, and me not wanting to reply because I hadn’t given thought to putting on a feminine voice.)

Next time out was a meal with friends. I decided that I was just going to be me, but in a skirt (and this is the approach I’ve taken ever since). I would meet one of them in the city centre and then we’d go to the restaurant together. The walk from home to the city centre, on a busy evening, felt like one of the the most terrifying things I’ve done.

I was hypervigilant, checking everyone’s reactions. Guys would look at my legs and chest, but not my face. Women were more likely to do a double-take (partly because my wig was styled, partly because I didn’t move in a feminine way, and partly because all the makeup in the world couldn’t hide the fear). I think one figured it out and gave me a sly smile. And that was it. Nobody pointed and screamed like Donald Sutherland in Invasion of the Body Snatchers, anyway (and I guess that’s what I was worried about).

The meal itself was fine. Once my friends got over the surprise of seeing me in makeup and a skirt, chat was fairly normal. (“So, how long have you been like this?” ~”Like what?”) One highlight was seeing diners at another table staring at me, then conferring, and then nodding or shaking their heads as they tried to figure out if I was a girl or a boy. On my own, that would be a concern. Surrounded by friends, it wasn’t a problem (and they were able to give feedback on how I could do better the next time).

It gave me the confidence to do it again, but with a different wig, and trying out different looks. The more you go out cross-dressed, the less fearful you are, each time. It also gets to be slightly less exhilarating, and more mundane, too. Do it often enough, and it isn’t something ‘special’, it’s just another part of your wardrobe. (Although I have been saved a couple of times when my girlfriend asked, “Bloody hell, you’re not going out looking like that, are you?!”)

First time out...

First time out…