[Frock Tales] To Posh, or not to Posh, that is the question

“Whether tis nobler in the mind to suffer the slingbacks and arrows of outrageous fashion….”; yeah, I’ll stop the pseudo Buttshakespeare and just get on with chatting about a gorgeous couple of outfits Cindy picked for me.

As I’ve said before, many many times, I have a weird sense of fashion when it comes to Sarah. Weird is contextual of course, most 52 year old biological males don’t spend an inordinate amount of time surfing retro fashion websites, trying to work out the difference between a US and a UK size 14 (they are different for your info, a US size 14 has a 32in waist which is about the same as a UK 16 – now you know). But Sarah, i.e. me (I did promise to not to the third person any more a while back but I still get the little twinges of guilt about talking about frocks and *me* which is mad) loves nothing more than getting a spam email from sites like “Retro-Stage”, who do the most gorgeous 1950’s Xmas dresses – just saying.

Pictured – Xmas is coming up, just saying.

I turn up for a session with a much too heavy backpack full of the flounciest, frilliest, puffy-sleeve-iest dresses, florals, polka-dots, the works. And Cindy, bless her, has to bend herself in interesting ways to get as many different angles and poses of me in said frocks.

I always feel a little guilty as retro isn’t that popular amongst girls like us; please feel free to correct me (I love getting others to fall in love with the petticoat-enhanced swing dresses). Cindy’s extensive wardrobe for her clients is full of modern things, club dresses, office outfits and the like. And she has the perfect eye for what looks good; to me if it flares as I walk, or has padded shoulders in a forties way, I think it’ll look good. I have convinced myself I can’t pull of normal, modern styles, mostly because in my time before I discovered someone who can actually make me look good I wore those kind of things, so my association is a slightly overweight me wearing makeup that looks like it was done by a hamfisted talentless makeup artist (i.e. me).

Pictured – yeah, I used to try and do my own makeup; this is circa 1995…

So I let Cindy have ‘dealer’s choices’, and she never fails to get it right. I’m always taken aback, even now after a ridiculous number of sessions, with her ability to choose exactly the right look. She gets this odd head tilt and you know she’s going to squeeze you into something you thought was a belt but turns out to be dress, and it’s always fabulous.

With this session I’d modelled a couple of gorgeous 50’s housewife outfits (see previous fashion blog). After four hours or so of swanning around in petticoats and pearls I thought it was fair to let Cindy have a shot, and again she hit the mark.

I’m going to get flamed for this, but I don’t get flared skirts. They are lovely but to me they are just a skirt. Correction, I *didn’t* get flared skirts until Cindy showed me the one in these outfits, a golden one. Gold! Dribble.

So the first look she went for was a ‘posh tottie at the races’ look. A white jumper combined with a very pretty white belt, the gold flared skirt, a gorgeous little white high-collar jacket and a lovely seventies style wig, with some flips. Throw in some white high heels and again my breath disappeared when I stared at the woman in the mirror. For a couple of years I was breathless all the time because I needed a corset done very, very tight to get near to an hourglass figure, but with this one the weight loss was starting to take effect so I had a 50’s style girdle along with a stomach clincher (yeah, modern on the outside, retro underneath).

Pictured – GOLD! Just right for a posh tottie on the pull.

A quick mention of the heels. When I was growing up the girls all wore power-dress suits to nightclubs, aside from the metal fans (tight black jeans, cut off t-shirts and leather jackets for those girls), and white heels were, well, the sign of a little bit of sluttiness. And that has stuck with me, so putting on white heels always feels a little, well, naughty. I know, little things, but still, seeing this woman in the mirror and tottering on white heels got my mind racing a little.

Pictured – nothing slutty about leaning in slightly to show the top of the cleavage. Nothing at all. Cough.

The look was wonderful; we did some shots as it was and then added a white fascinator and a glass of champagne for that ‘rich tottie’ look. Exactly the type of woman who’d never look at the drab version of me; and the slightly (cough) bitter person inside me was secretly thrilled that I could pull off the look. Again, sailing into kinkier waters, I can imagine having this look and going to a busy pub in London, perhaps Canary Wharf, and just seeing what happens. Actually forget that, we all got screwed by bankers back in 2008 and I can’t imagine it’s any better physically.

Pictured – the thought of sleeping with a rich banker seems to give her issues

I loved the look so much we decided to keep the foundations but go for a different type of girl; we kept the skirt and white jumper but added a denim jacket and accessories more suitable for an American ‘Valley Girl’. Again, another type of girl who would cross the road to avoid making eye contact with the dishevelled rock fan look Mr.Drab has and again, so much fun to go over to their side for a bit.

Pictured – “Oh Chantelle, that handbag is so YOU!”

It was getting later in the day and I was feeling a little braver than normal so we took Valley Girl out of the apartment and down to the door. I’ve talked in length about my (seriously irrational) fear of being outside as a woman, and even standing with a closed door between me and the real world gave me that hot, metal thrill all the way through my digestive tract. Some people like that feeling. I’m growing to like it.

Pictured – I was just waiting for the door to click behind me, or to hear someone coming down from the upper floors, and I would have shot back up the steps and into Cindy’s place at a high speed, regardless of heels…

I love the difference between the two women Cindy created. You get the feeling posh tottie would look down her nose at Valley Girl. And Valley Girl would laugh at posh tottie as she walked away.

Way too much fun, and way too easy to slip into those mindsets. Cindy’s Dealer’s Choices are hypnotically delightful. Maybe I should do some more….

Stay beautiful and if you get the chance, let an expert tell you what style would work for you. Plus retro of course; everyone should do retro at least once.

Pictured – “So, the boyfriend was like, lose the sunglasses doll, I like to see your eyes when you’re pleasuring me, and I was like, no way!”

9 thoughts on “[Frock Tales] To Posh, or not to Posh, that is the question

  1. Another great post and touching on a subject I always find great fun to think about – would ‘he’ and ‘she’ ever have been romantically involved had they met in the real world! I can say with 100% certainly that male me would have had a major crush on female me (actually, he does!) but, short of a miracle, it would never have been reciprocated! Would love to hear your thoughts here too.

    I love the two looks by the way!

    Liked by 1 person

    1. Drab me definitely adores Sarah; I often say that CDs/T-Girls always dress the way they want women to dress. As for reciprocating, no way, Sarah could do much better πŸ˜‰πŸ˜β€οΈ


      1. I feel the same. I can only speak for myself but the paradox I wrestle with is that whilst I learned long ago that, to stand any chance with the type of woman that I admire (and want to emulate) I would need to dress in a consistent way – i.e. suit/tie and smart casual – I am happiest just looking scruffy. And so begins the self-fulfilling prophesy!

        Liked by 1 person

  2. Absolutely love this post sweetie! 😊
    I know that Retro is still your first fashion love – and rightly so! But it is lovely to see you in different fashion choices that Cindy makes for you. And you are of course so right. Her eye for style and what works is exceptionally keen! 😁
    I love these two looks Sarah. πŸ™‚ I think posh totty would be perfectly at home screaming at the Gee-gees at Goodwood and that valley girl also wouldn’t look out of place around Sloane Square. πŸ™‚
    I these that there sophisticated non – retro looks should definitely be a part of your feminine repertoire Sarah. πŸ™‚ 😘 ❀️

    Take care my wonderful (posh! πŸ˜‰) friend. 😘 πŸ’‹ ❀️


    Liked by 1 person

  3. Hi Sarah,
    I too love the Retro look but I do take myself to fabulous events such as Goodwood Revival where I am able to wear my outfits in public and have a fabulous time. I’m sure you would love it too once you got over your β€˜fear of flying in heels in public’.
    Like you I enjoy the fabulous dresses and accessories from the 40’s and 50’s, which give an element of nostalgic glamor to the way we dress.

    looking forward to more of your dressing adventures and musing.

    Dawn x

    Liked by 1 person

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