transretrogurl

I’ve been dark lately so time to cheer up with a little humour. As a fifty year old man with little to no actual fashion sense (in drab) I’m getting used to the delight and fun of shopping for women’s clothes. Well, not for women’s clothes as such, but for Sarah’s clothes.

And as such my choices for outfits can be, well, a little odd at time. This is because a: I have no experience of clothes shopping contrary to popular belief and b: I’m an impulsive buyer.

Being an impulsive buyer means I’ve bought a lot of stuff, some of it just sublime and wonderful and some of it, well, ‘questionable’ would be being kind.

Now normally we feminine-few band of sisters tend to only show and share the best of our pictures because, well, we don’t have a huge amount of confidence due to being in the wrong skin/gender/toilet-according-to-some-bigots so our online presence is mostly the best of our pictures, often enhanced digitally because why not, the world is doing it.

But for every wonderful shot, at least for me, there are a number where I’ve got it wrong. And hence the title of this blog – I’m going to share some of the wildest and funniest mistakes I’ve made in the spirit of openness and hopefully as a measure to cheer people up.

Caveat – these mistakes were mine and mine alone. Cindy at Boys Will Be Girls will always help and assist but I can be wilful at times. And to be honest they are not mistakes, just near-misses; I actually like a lot of these looks but they don’t get the circulation of the other ones because they didn’t quite work. But see for yourself, everyone’s tastes are different….

1: Off to Clown College….

Pictured – you may have to turn the contrast down on your monitor/iPad. Or put some sunglasses on.

I like this frock a lot but it is way too busy. It’s the kind of print that needs oodles of tattoos to make work in an ironic retro way and subtlety isn’t really it’s main selling point.

We refer to this as the ‘clown’ look which is a little unfair. But funny.

2: Soviet-Era Receptionist

Pictured – may I see your papers, comrade?

Nice enough frock but a little restrained and uniformesque. Needs a wooly hat with the red star of Mother Russia to top it off methinks. Again, I like the frock but the result was a little too uniform to be fun. Although a day in it behind a desk wouldn’t be that bad an experience.

3: 1970’s Dance Diva Disaster

Pictured – just need a 1970s pimp in full pimp costume and the picture is complete

There’s a reason you very, very rarely see me in trousers enfemm. For a start I’m tall and a little bloke shaped, which means the tight catsuits and leggings are not designed for someone of my leg length and body girth.

With this outfit I decided to go for it but went for a very large size just so I could get my torso in it and give the legs at least half a chance to be covered. But it didn’t quite work – the most difficult part of it was, and not being crude, that these outfits are designed for people without external bits and pieces. Even tucked this outfit was like wearing cheesewire when I bent down, with the crotch area trying very hard to be inside me. Comfortable is not a description I’d give it.

Plus Cindy has taken to calling the wig the ‘Brian May; one which makes us laugh but takes away a bit of the femininity of it all.

4: Dressing up in Mummy’s clothes

Pictured – I’ll be the first to admit it. I’m not a size 22. Even if I think I am because I haven’t exercised. Of course, Cindy thinks I can fit into a size 14 but that’s the other end of madness

Another Kitty frock I’m afraid. There’s a bit of history to this one – this is the first of the Taffeta ones I bought and I was feeling pretty crap about myself when I bought it. I’d been modelling a number of Kittys and always went for size 20; they tend to size up a little small and the size 20, I thought, was my size. Well, turns out a size 20 has a lot of give when I put it on and we always combined them with a belt – in fact now I can get away with a size 18 in a Kitty quite easily.

But I’d convinced myself I was overweight and bought the size 22. Whoops. It was a very high quality tent. Me and Cindy tend to refer to this as the ‘sack cloth’ moment. However I did return it and get a properly sized one and the results were wonderful.

Pictured – the correct sized frock 🙂

5: Everything that was wrong about 1970s fashion in one picture

Pictured – sometimes retro fashions need to be left in the past.

Really not sure what I was thinking here other than ‘why not find the worst example of a 1970s maxi dress and then don’t wear tights as it could be one of those ‘mothers who is embracing women’s lib’ kind of scenarios’.

I did a session where we did minimal makeup to see what Sarah would look like if she wore normal women’s makeup. Turns out I look exactly like my mother did in the 1970s right down to the expression she had when she first caught me pinching and wearing her clothes.

Still fun doing it though.

6: Cowgirl – Yippy-ay-Nay Muddyfunsters….

Pictured – and the other end of the size spectrum. When your dress won’t cover your boobs

I bought this outfit on a whim and like all women’s fashions you seriously roll the dice when it comes to sizing. When it arrived I whipped it out of the packaging and tried it on in the bathroom and, whilst it was a snug fit, it fit fine.

Of course you kinda forget when you’re trying on stuff in ‘middle mode’, which is what I call it when I throw on a frock for sizing and make very careful not to look above the neck in the mirror, that you’re sizing the frock against the male shape. And, aside from a little bit of beer boobs I don’t have any swellings where women have swellings.

Fast forward to the session and once the boobs were on there was no way that frock was going to do up. No way in heaven. Plus it was made of a material that had absolutely no give in it, so we had to settle for a very slutty cowgirl.

7: The 1960s, when a mini-dress was barely a t-shirt

Pictured – desperately trying to make the frock just an inch or so longer. And failing.

Turns out the 60s were pretty much a decade of sexual discovery and excess and nothing is more obvious about that statement by the lack of length of a proper 1960s minidress. I bought this one because I loved the pattern and collar and assumed, wrongly, that it would be a complete dress. Instead it was barely a belt. All of the pose were of me desperately trying not to show my knickers, which I guess was the actual point of a minidress in the first place.

8: When the disguise is actually too good

Pictured – for some reason this was uncomfortably convincing. Go figure….

This is an odd one to find on the Ms.Near Miss pile because the look worked, but it worked too well.

Let me explain that as it sounds but isn’t immodest. I dress for the ‘click’ as I said a couple of blog posts ago, that moment when your entire body and soul does a little squee at seeing something completely different in the mirror. This look actually made me uncomfortable because it is how I would be if I was a woman.

The kinda submissive, quiet cute look of the outfit just had me staring in the mirror and thinking ‘hellfire, I could transition and be this person every day’ and that caught me out. This look wasn’t escapist fantasy, it was a glimpse of another life and that broke the moment a bit.

Anyway, I have probably three photos from this look that I use occasionally. The rest are tucked away for when I’m feeling odd.

9: ‘Let’s stop doing glamorous poses for a second, I want to look like your middle-aged mum cleaning up after you’

Pictured – you kids never clean up after yourself and always leave it to your father or me to do

Sometimes the camera catches you at just the wrong moment. This is one of those. Granted, it’s a funny picture, but not one to fuel the glamour obsessed woman inside.

Still funny though.

10: ‘You need to plug it in, dear’

Pictured – I have a PhD in AI and have written multiple systems to analyse sentiment in text and predict behaviour based on it. And yet I don’t seem to realise you need to plug the vacuum in

Tongue in cheek but wow, you wouldn’t believe the number of direct messages and mails I got from helpful men explaining how to use a vacuum. It was like they couldn’t focus on the fact it’s a gorgeous floral frock or a portrait of domesticity. And a lot of those messages were completely genuine.

I know how a vacuum works. Now.

11: This year’s contender for the ‘what on earth were you thinking, Sarah?’ award

Pictured – ‘let’s take a picture of Sarah on the toilet reading a Cosmo because, err, umm, err’

My underpants were firmly up and it was completely in jest but still, misfire, misfire, misfire.

Again, funny though….

12: Dressing for the funeral of a friend

Pictured – the range of poses and emotions you can show when dressed for a funeral are…..limited

Seemed like such a good idea in my head – get a posh black frilly high necked blouse, pinch one of Cindy’s pencil leather skirts, use the short ‘Jane Fonda’ style wig and let’s see what Sarah would look like if she was going to a funeral.

Problem with that scenario is that you can’t pose ‘all fun’. Something about the solemnity of the idea makes it seem irreverent so I ended up with some (very nice) pictures of a solemn looking Sarah.

Nice blouse though.

13: Be *very* careful what you read…..

Pictured – the picture that launched one hundred emails

So, I grabbed a copy of Cosmo which I’ve never read in my life for a prop as part of a ‘ditzy secretary’ look I was thinking of. Cindy provided a wonderful frock and a look, and whilst taking the pictures I was skimming the articles when I came across this one.

That smile on my face is a look of humour but unfortunately most of the viewers of the photo, which has been taken down off of the Social Media site where I put it, took it as an invitation.

I lost count of the number of emails and messages from men asking a: if I would peg them or b: if they could peg me.

Not my finest moment of sense.

Still funny though.

And that’s pretty much it for this post – thanks for sticking with me, I wanted to try something a little different and it’s always nice to smile at yourself occasionally. Of course I have hundreds more of these type of photos – you don’t have 17k pictures taken of yourself without looking like you’re sneezing or mid fart some of the time. But I’ll save those for when we need a laugh again.

Stay beautiful and remember that we’re not perfect. Just mostly perfect. Most of the time.

Pictured – and sometimes you are allowed to make questionable fashion decisions. Just for the hell of it…..