[Fashion] A retro re-discovery with lots of Squeeeee.

So, a little secret, just between us. I was thinking of winding back on the Sarah time, not for any real reason not to do it, but because it is a stressful way of life, regardless of how much I let the inner girl gush about it. Real life is a drag, pardon the expression, and I’ve left all the little stuff become the big stuff. So, I had a two day session planned, as a little 50th birthday present to myself, where I’d give Sarah one last bit of fun before quietly putting her back in the pink room.

It’s a side effect of depression and I’ve talked a lot about the purge/binge/purge cycle, but this felt different, a little sadder. But, dear reader, don’t be down, because, well, something odd happened at the sessions. Something clicked, something rose to the surface that I had kind of forgotten in the four months since I last slipped on the stockings and fidgeted awkwardly while Cindy, of Boys Will Be Girls fame, desperately fought with my wriggling face to do her magic. Something I’d genuinely let fall by the wayside a bit, which is ironic given the name and original nature of this blog.

I remembered how very, very much I love dressing in retro fashions.


Pictured – as evidenced in *every* one of the pictures of this look.

Amusingly, it only came back to the surface because Cindy, bless her cotton socks, had got her hands on some tools to do Victory Rolls. And it was as simple as that, on with a 1940s emerald green beautiful frock, up with the hair into the wonderful 1940s style, on with the sensible yet sexy heels and my breath caught in my throat. *This* is why I started the blog, this is why I shave the Chewbacca fur off, this is why I go through the hassle of travelling so far with such heavy luggage.

And wow, was it worth it. It was an epiphany of the most gorgeous sort, a pink, perfumed mist coming down into my mind and the love for it all was back.

So, before I give you a long and probably very boring look at the styles we did in the last two days, eighteen hours of retro posing, laughing and letting the loveliness flow back into her veins, I need to state what happens next.

Retro. From now on, Sarah is that kind of girl, the one who always wears the flowing 1940s and 1950s frocks, the one with the ruby red lipstick, the old fashioned but simply beautiful red nails, the coiffured hair.

Why? Because the feeling I have when I am Sarah and wrapped in retro clothing is simply indescribably wonderful.

So, I’m not going to put away my feminine things but instead when I need to feel better, when I need to feel that the world isn’t a terrible place, I’ll be throwing on a comfortable frock and heels, and going back 75 odd years…..

Anyway, the session ๐Ÿ™‚

Look 1: Pink Housewife Fun


Pictured – Pink Housewife but I think I see a bit of Meryl Streep in there ๐Ÿ™‚

This was my ‘warmup’ frock for the first day – I did a look a while back with a 1970s style housewife frock, pink again, and I loved the look. I found this dress on Joanie Clothing and the combination of the frills at the front, the gold buttons and the lace top of the frock, combined with the style and shortness just made it cute.

Chuck in a tight pair of Pink heels, which reminded me how hard women have it in terms of (non) comfortable footwear, my Queen of Hearts anklet (a gift from a lovely friend), pink nails and a makeup that mixed retro and a gorgeous set of pinks, and it was a serious bit of pink girlie time.


Pictured – ‘I hear hubby’s keys in the front door!’ ๐Ÿ™‚

Mindset behind it? Love channeling the stay at home housewife look and the frock was surprisingly comfortable. When wearing it Sarah wanted to pull herself in a bit, if that makes sense – legs tight together, shoulders in tight. Lots of fun and great starter dress.

Look 2 – My First Collectif Clothing dress, by Sarah, aged 9


Pictured – ‘Squee’ for all the wrong reasons ๐Ÿ™‚

So, this one was a lot of fun but a little odd – I saw this outfit (it’s actually a separate top and dress) advertised on the Collectif Clothing site and fell in love with it, but….. to be honest….. who is this actually aimed at? When I put the outfit on and had a twirl in front of Cindy I asked that very question, and with a brief pause we both said…. ‘Transvestites’.

I’m not sure what modern woman would be comfy wearing this to work, for example. It has somewhat of a little girl (you think???) look to it that just makes it an odd little combo. But I’m not complaining, it was gorgeously cute to model and a lot of fun to pose in.


Pictured – also would go well as a square-dancing frock…

The combination of the collar, which is a gorgeous twist on a Peter Pan, and the puff sleeves give it that ‘girlie-girl’ look, and combined with power-blue gingham it just screams cutie-pie, which does take me back, inevitably, to just who this is aimed at?

Crossdressers. ๐Ÿ˜‰

As they say, if the flowing skirt and puffy sleeved blouse fit…..

Look 3 – Not in Kansas any more Toto


Pictured – ‘insert the obsession with Judy Garland that many of us have here’

Yeah, we couldn’t resist it – Cindy has a little stuffed Toto in a basket and we thought the outfit was *very* Dorothy, so a quick change of hair, couple of pigtails, and the ‘who is this aimed at’ outfit really took on a different look.


Pictured – yup, perfect for the modern executive woman who wants to make a statement in the boardroom

Look 4 – Grace, the robot 1950s fashion inspired Mom from ‘The Umbrella Academy’


Pictured – Yeah, I thought having her reading that fantastic book of 1950s housewife articles, ‘What Every Woman Should Know’, would be fun as well….

So, I found myself watching the Umbrella Academy a month or so ago on Netflix, and while it was a superb sci-fi/superheroes story I found myself getting very obsessed, and a little hot under the cover, at the sight of the ‘Grace’ character. She is a robot created by the man who founds the academy, designed to be a mother figure for the children who are brought in, and is always immaculately dressed in 1950s housewife outfits.

So watching that series was a little hard whenever she was on. And, in my usual fixated fashion, I thought it would be great to roleplay her, a modern take on the Stepford Wife paradigm I love so much (again, for all the wrong reasons).

So I tracked down a gorgeous couple of 1950s dresses, one in a mint green, the other in a bright yellow, both the same style. For this session I brought the mint one, and, combined again with a Victory Roll inspired hairstyle, copious amounts of fluffy petticoats and some very hard to walk in heels, I became Grace. And yeah, it was as good as I thought it would be.


Pictured – ‘Now behave children, it’s time for bed’

The material on this frock was gorgeous, a kind of satiny/shimmery feel that made it feel slightly cold against the skin. I also love the buttons on the cuffs, a very 40s/50s thing that adds a degree of femininity to the outfit for some reason.

Kinda fell in love with this look, but there were even better ones to come in the session.

Look 5 – Amy Winehouse as a 1950s Diner Waitress


Pictured – ‘Fries and a shake, sir? What flavour shake? Bootie? Behave!’

So, while doing the Grace look it occurred to me that if I added an apron and some accessories that mint green frock would make a lovely Diner Uniform, very like the Twin Peaks ones (yeah, I used to watch Twin Peaks and get distracted over how nice the Diner uniforms were).

So Cindy did her magic with an up-do, put a lovely scarf in the hair, gave me a pad and pen, tied an apron on and et voila, Amy Winehouse as a waitress, which ticks two of my secret fantasies at once.


Pictured – ‘Your beers sir. Does it come with a smile? Depends on the size of your tip.’

It was a lovely look – we also did some wonderful candid shots that were astounding. I don’t think I pass well (no crossdresser with confidence issues, stubble you can shave metal with and a foot or so taller than the average woman does really), but some of the candid shots, especially ‘waitress take a break and has a piece of fruit’ seemed to catch something vulnerable and feminine I hadn’t seen before. And I loved seeing that.


Pictured – Little secret? I was starving so the banana eating was a cheat to get some food. Yeah, I know it’s phallic but it tasted deliciious

Look 6 – The Banker’s Wife, revisited


Pictured – the blackmailed man ๐Ÿ˜‰

Yeah, it’s a tranny cliche, but the ‘Banker’s Wife’ set of pictures I’ve done over the last couple of sessions have been a hoot. The whole premise is a man is blackmailed by his unscrupulous bank manager into acting as the manager’s wife for some official functions. Gives me a chance to play with the more mature look, and the more conservative dress style.

So this frock was from Joanie Clothing, a full button up dress with a belt – we combined it with what we call the ‘Jane Fonda’ wig (because to me it looks like the hairstyle Hanoi Jane had in 9-to-5) and did a shoot where I did my best to look sullen.


Pictured – ‘The Kept Woman’. Ahh, one can dream ๐Ÿ˜‰

Bit of a giggle as always…



Pictured – speechless. This is the way I always wanted to look but thought it was impossible to get my middle-aged, poorly treated body to look like. Guess I was wrong. Wow.

Yeah, the next look was something else. I get a thrill when the wig goes on and when I see the final complete outfit in Cindy’s well lit dressing mirror, but this was something else.

I actually asked Vivien of Vivien of Holloway if they would ever do an animal print Kitty, and two months later one appeared. I actually sat on the website the day it was released, credit card in one hand, the other bashing the refresh button until the item appeared as available, then rushed to get an order in. And then had to wait four months to try it on.


Pictured – worth the wait. Completely.

I was not disappointed. I love all the Kitty frocks – the styling, the shoulder pads, it all plays to my love of the retro female form and shape, but this one was something else. Cindy outdid herself with the hair – a gorgeously long red-head look with Victory Rolls.

This is one of those outfits that took my breath away when I looked in the mirror, and raised the question that if I ever got into a situation where I was thinking of transitioning, this is how I would dress every day. The look just reminded me of all the retro-styled women I’ve seen who are obviously over the moon to dress that way. The smile, the light in the eyes, it says it all.


Pictured – call it narcissism but I love her look *so* much it hurts ๐Ÿ™‚ย 

This will be a revisited look – and also this outfit was the moment I decided retro is the thing I want to do all the time, and Sarah wouldn’t be going back into her pink flat at the back of the middle-aged man’s mind.


Pictured – Thanks darling xxx

Look 8 – The Insane Impulse Buy

Fun story around this. So, I got to London on the Wednesday, did a day in work, finished at around 17:00 and had a sudden impulse to actually go to the Vivien of Holloway shop and buy a dress for the next day.

It was rush hour, so it was a daft idea to start with. Add the fact the shop closes at 18:00 and, more importantly, due to my mental anguish (and IBS lately) I’ve developed an anxiety issue with going into a shop andย actually having to talk to people and yeah, it was an idea of the daftest nature. But I thought, what the hell, let’s try it and see.


Pictured – spoiler alert. I bought a dress there. End spoiler alert.

So, the Tube was *packed* and I had to travel from Monument to Kings Cross, then hop on the Piccadilly up to Holloway Road. Masses of people at Kings Cross and my anxiety was spasming all over the shop, if you’ll pardon the phrase.

Eventually I got out of the Holloway Road Tube station, it was twenty-five minutes to six, the shop itself is two and half minutes down the road, so I yomped on down, found the place, opened the door and stepped in.

Heaven. That’s the only word for it. The staff were fully retro-ed up in gorgeous Kittys, the walls of the shop were packed with rack upon rack of floral, pink, yellow, blue dresses, shelves with hats, flowers for the hair, handbags. And of course, I was stood there, scruffy jeans and hoodie, stubble, obviously not the usual clientele even though I’ve spent WAY too much on Vivien frocks over the last ten years.

They were preparing to close but one of the staff smiled pleasantly in a kind of ‘what are you doing here’ way and asked if I needed help. I trotted out the standard cross-dresser lie – I was looking for somethingย for the wife. And then I kinda shot myself in the foot because when she asked what kind of thingย my wife would like I immediately said ‘Runaround Sue, the new print’ before my brain could put the brakes on.


Pictured – You know, very similar to this one. *cough*

I’m pretty sure the lovely woman who served me read me then but she was nice enough to play along. ‘What size is you wife?’ she asked, and again, before the brakes could be applied, I blurted out ’34 inch waist, usually a 20 in your sizes’. Doh.

With a very subtle ‘you’re very good to know that’ the lady lead me over to the Runaround Sues and there was a size 20 in the lovely new Pink pattern, which I grabbed and took to the counter.

So far so good, I had enough money in the wallet (although I described it as a ‘purse’ when I posted to the Vivien Facebook page that I had bought a frock, from Sarah’s FB of course), handed it across and asked ‘do you have a bag’.

I swear she had the moment of an amused glint when she said ‘Of course, when you buy a dress you get a complementary Tote bag’.

Oh dear. So, I ended up travelling back on the Tube to the hotel, grizzled bloke in jeans and a hoodie, carrying a gayly coloured Viv of Holloway tote bag, proudly proclaiming ‘the best 40s and 50s women’s fashions!’ in bright pink.


Pictured – this very bag. Nothing says ‘I am a closet cross-dresser’ louder than clutching this on a packed Tube and looking guilty….

Anyway, *what* a dress. The fit is perfect – it has a single zip from the bottom of the shoulder blades to just above the hip, the collar is fixed (which is a little challenge to squeeze your head in when you have a face full of warpaint on), but the flow of the dress is lovely. Cindy combined the look with the ‘Svetlana’ hair, which is a lace-front blonde number, and it just worked a treat.

Having literally just rediscovered my overpowering love for retro this outfit just made it so much better.


Pictured – *totally* worth the terror, uncomfortableness and panic attacksย 

Look 9 – Re-visiting the Banker’s Wife Frock.


Pictured – deliciously prim and proper

This was the last look of the first day and having done retro all day I fancied something a little different. This frock is a favourite of mine, for a lot of the wrong reasons – it’s very 1980s, very mumsy, very mature lady, but I love dipping into that character.

Instead of using the Jane Fonda wig we used the one we had used for the mousy housewife, and I did the usual set of looking forlorn.


Pictured – I’ve been practising letting the wrists go limp….. seems to work nicely ๐Ÿ™‚

Plus I have a soft spot for the frock, it’s always a lot of fun to wear….

And that was day one – day two was a slightly shorter session, eight hours instead of ten, and I decided overnight I wanted to do another pure retro session. That epiphany around loving, or rediscovering my love of the retro fashion really got me excited. Sooooo….

Look 10 – Retro Perfection….


Just wow. I asked Cindy if we could redo the Victory Roll look, and I’d bought one of my 1940s tea dresses, a look I’ve done before (and I love this dress so much). But the combination of the red hair, the Victory Rolls, and the outfit just took my breath away.

I’m seriously starting to think that I was a woman in a previous life, around the 1940s, because those style dresses just reach into my soul. The fit, the way the skirt flares, the buttons, the collar, just everything. And the colour of that frock just reeks 1940s in a glorious way.


I did a lot of squeeing internally with this look, and it shows in the pictures – those are genuine smiles, and the use of the V for Victory symbol just adds something.

The main picture of this blog is a B&W version of one of the outside pictures, and I love it. Also did the one below, which could double as a picture from an article on the 40s (in my humble opinion, of course ๐Ÿ™‚ ).


Look 11 – 1950s Uber Glamour…


Pictured – channeling my inner 1950s film starlet

Another impulse buy, this time online – I have worn the Taffeta Kittys from Vivien of Holloway a number of times, but when I bought them the colour range was fixed to single colours (I had the lovely metallic purple one). Recently Viv brought out this dress, which is silver base with black stripes, and it’s just completely gorgeous.

Also, because of the material, it stands out as you wear it, as if you have a petticoat on, which is disconcerting at first but when you get used to it is a lovely effect. Add in the fact the material is like delicately iced satin against your skin, and you really feel luxurious wearing it.


Pictured – it’s all in her eyes….

Serious amount of squeeness, to the point I thought we had to pose an ‘advert’ style look for Vivien of Holloway, using the bag that gave me so much grief on the Tube in a way that redeemed it perfectly….


Pictured – and I posted this to the official VoH Facebook site because, well, this is my extreme sport ๐Ÿ™‚

Look 12 – The first of my GORGEOUS birthday presents from my darling friend


Pictured – the *perfect* party frock for Sarah

I may have mentioned it was my 50th birthday last week. A couple of times at least. Drab me didn’t celebrate, brusquely nodding at people when they congratulated him on managing not to die for half a century. But Sarah, different matter. A lovely friend of mine decided she needed to get something special, and she did. Two gorgeous vintage style frocks from a speciality shop.

What was lovely about this, and I was touched to the point of a tear or two, was that they fit perfectly, they were a wonderful modern take on retro that worked to a treat and, I dare to say it, they were items of clothing bought by someone who loves Sarah, and that was touching.

Do I have something in my eye? Yes, that’s definitely it…


Pictured – and as for my my darling friend? The first and last dances are yours, sweetieย 

This frock was the first of the two I tried on – green satin with a perfect little floral motif. Lovely.

Look 13 – The other part of my glorious birthday present


Pictured – happiness in a gorgeous party frock. Yet when I look in the mirror in drab mode I see a fat person. Go figure…..

The second frock my darling friend gave me was as lovely – this time we combined it with the hairstyle that has come to be part of the Sarah look. Chuck in a red rose for her hair, and retro party wonderfulness.

Both this one and the one before were perfect fits and felt gorgeous against the skin, I highly recommend having a peek at the website for the shop at https://misssamanthasvintage.co.uk/


Again, a wonderful birthday present that bought tears to my eyes. And given the amount of mascara, false lashes (top and bottom) that was an interesting experience ๐Ÿ™‚

Look 14 and the Final One – the return of Svetlana


Pictured – rocking the East European prostitute look, he says in a completely un-PC way

For the last look of the two days we decided to have a bit of fun and break Svetlana, Russian mail-order bride from the Ukraine with a very bad grasp of the English language, back for a quick visit.

Cindy painstakingly added 80s style blue eyeshadow over the retro makeup to give it more of a modern look, squeezed me into what she called a dress but what I was sure was actually just a belt and, to add amazement, a size 10 cool jacket. Yup, you read that right, a size bleedin ten. Putting this in context, when I started coming to Cindy’s I’d comfortably fill out a size 22 frock and still look like a sausage about to explode, so no-one was more surprised than me when it actually went on. I did claim that I have magic powers that allow me to fit into whatever piece of sized female clothing I have a soft spot for, but still, a size ten? Yowser.


Pictured – again, just let the wrists go limp in a way that would have got you pummelled at school in the 1970s

Anyway, lots of fun ensued with use of the patented ‘resting bitch’ face, combined with Svetlana’s world-weariness of being a purchased wife. Always good to finish the session on something delightfully sexist, but as I’ve said before, I’m not sure sexism comes into it when you are doing it to yourself, if you’ll pardon the expression…..


Pictured – Da, that is blue darlink.

And that was that, an hour after that gorgeous picture was taken I was standing in the crowds at Euston, amongst drunken football fans, harried families heading home, everyone lonely yet surrounded, but I was happy, happier than I’ve been in a long time.

Why? Because I’m a fifty year old man with a lot of demons, but I’m also the woman below, and the woman below is just so deliciously wonderful to be and to know. And you know, I want to have more adventures with her, she’s a lot of fun.


Pictured – me. xxxxx

Stay beautiful, stay true to yourself, and remember that the only person you have to be comfortable with is the one that shares your skin.

3 thoughts on “[Fashion] A retro re-discovery with lots of Squeeeee.

  1. Oh this is wonderful Sarah! ๐Ÿ™‚XXX
    A beautifully well written post.
    I admit that I was a bit surprised (and worried!) that hairy masculinity had almost got the better of you. But I am sooo glad that it didn’t! ๐Ÿ˜Š ๐Ÿ˜˜ XXX
    I am delighted to hear that you have rediscovered your inner retro girl sweetie. ๐Ÿ™‚ I think she is a totally intrinsic part of you and to deny her would be detrimental to your wellbeing.
    All of your outfits look spectacularly gorgeous! I totally agree about the animal print VOH dress! Stunning beyond words! ๐Ÿ˜Š XXXX
    You just keep being you Sarah. ๐Ÿ™‚
    Stay safe sweetie. ๐Ÿ˜˜

    Liked by 1 person

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