[Fashion] Good Lord, Goodwood….

Ooo, I’m going to gush a lot in this post. I’m not an ‘outside girl’, I get easily terrified if I’m away from the safety of male clothes, even though I bemoan them all the time and secretly, or not so secretly, yearn for the chance to be out and about in, gasp, the real world in a lovely frock, and being out always seems to bring out the worst in me. My anxiety and fears that someone will point, laugh or, given the current climate, attack me have had too large an input into my behaviour for too long.

I love dressing up in retro clothes. Yeah, I’ve not been shy in saying it, but I spend an inordinate amount of time on Instagram looking at the wonderful pictures from women who get a chance to go to events fully in character, and I always sigh wistfully with a ‘nah, not for me’ mindset.

Pictured – yeah, I may have mentioned my love of retro fashions just a little bit before….

So when a dear, dear friend of mine suggested earlier in the year that we both frock-up as vintage housewives and spend a whole day at the Goodwood Revival it triggered all my best, and to be honest cleanest, fantasies. And I said yes.

I have literally spent nigh on every day since that fateful conversation, up until this last Saturday, terrified at the idea. I’ve never been out for more than a couple of hours, and when I have it’s always been somewhere container. The thought of throwing on a gorgeous 1940’s tea dress and then being unable to hide was amazingly scary.

In addition the day would entail a number of firsts; I’ve never been to Brighton, never walked through a hotel lobby in a dress and heels, had no idea where Goodwood was compared to Brighton other than it was a bit of a drive.

Pictured – Looking through my archives for retro images is an easy task. I have worn a lot of 1940’s dresses

Luckily my friend, who has the same kind of military grade OCD that I have, took it on herself to organise everything. Again, this was new for me; I’m used, and comfortable, with owning all the responsibilities. I was handing off that, and I’m going to be completely honest, I woke up pretty much every day for the last two month with a rush of ‘Oh God, what I am doing?’. I convinced myself that there were too many moving parts to the plan, and that, at the end of the day, in the bright lights of natural sunshine compared to the closeted and safe photo studios I work in normally, I’d look like a Rugby Player in drag.

To cut a long whinge short, I was terrified of the whole idea. But I still wanted to do it. Just the once. A chance to be one of those women, in public, enjoying the experience and dressing to be seen was something I have craved for so long but, because of my caution (/cowardice) have never tried.

And then a week before the event, the Queen dies.

Having served in the military and been brought up in a Royalist house I always thought the Queen would be there forever. And it changed the landscape of the preparation; now I’d have to get into London at the height of the mourning period, and out and back on the day before the funeral.

My friend had arranged for a professional wig-maker (used by theatre and television) to do the hairpieces, and I headed into London (getting up at 3:00am), sat in my work office (on my day off!) until the wig place opened, headed across London in rush hour, picked them up, met my friend at the office, walked over to London Bridge and we were off to Brighton.

Pictured – I did toy with the idea of getting a Victory Rolls wig but when you are ducking in and out of a taxi, walking around a field in the wind, it’s not going to stay pristine for long, and I have zero ability to repair any work of art like that

We stayed at the Grand, a lovely retro hotel which seemed perfect for the fun we were about to have. The night before the Goodwood event we hit the town, found a lovely restaurant, had a superb meal, then back for absolutely no sleep; I was so anxious that I was awake all night staring at the ceiling asking myself what on earth I was doing. I was convincing myself it would be a disaster.

At 7:30am the next morning the Make Up Artists arrived at the room. They were delightful, a couple of extremely talented, warm and wonderful women who were determined to make us both look perfect. I went for a pure 40’s look; I’ll talk (in length) about the frock in a second, but I was, again, terrified, this time about my eyebrows.

Pictured – I didn’t take a lot of photos (37) because I was genuinely enjoying just being Sarah but here we go. I *love* that hair-piece and the makeup was jaw-droppingly good from a genuine 1940’s look perspective.

I don’t do anything with my manly brows. I don’t style them, barely trim them, as they are my last line of defence in pretending (albeit quite badly nowadays) that I’m a ‘normal bloke’. Whenever I have a photoshoot it takes such a long time to conceal the brows and I was concerned that the MUAs wouldn’t have had experience with a hairy 53 year old transvestite. I needn’t have worried, she was brilliant and did a great job of hiding them before painting some delightfully delicate 1940’s brows on.

After she finished the work (I never look in the mirror during a transformation as I don’t like seeing the gradual shift; I want to look and see Sarah with no traces of drab-man) I gingerly peeked into the mirror and my breath caught in my face.

The makeup was exquisite. To me, who was looking for the smallest imperfection, the smallest piece of proof that I was a bloke pretending, I literally couldn’t see anything other than an older 1940’s woman. The transformation was stunning. Once the hairpiece went on, and the, squee, the frock, it felt delightfully, terrifyingly normal and, well, right.

Pictured – all the proper accessories as well; I lovely flower combination for my hair and a pair of retro sunglasses bought for me by another dear friend

The frock – oh Lord, I always used to get frustrated at how long my first wife took to pick an outfit when we were going out but me? I was way worse for this event. I had five candidate outfits; my gorgeous racing green 1940’s hostess dress, a new swing dress from Collectif (bright red with white polkadots), my floral House of Foxy authentic day dress, my latest Vivien of Holloway Kitty (red floral) and a brand new tea dress I had bought at the last moment.

The tea dress was perfect. It was a light brown check pattern but the styling was utterly gorgeous; lovely shape and I’d managed, due to the weight loss, to fit into the ‘large’ size. When on it felt comfortable, figure hugging and just delightfully 1940’s. And it had pockets, for my 21st century essentials.

By this time the chauffeur had arrived and I had that one moment of ‘this is your last chance to stay in the hotel room; the minute you step out of that door there’s no coming back until you’ve been Sarah in the real world for a whole day’. The sound of the door clicking shut behind us as we stepped out into the hallway was like the sound of the last chain being broken.

I had some wonderful heels on (more of that in a moment), some authentic tights, a lovely handbag with emergency supplies in it (Chanel No.5, my bank card, spare pair of tights, spare glue for my nails, spare nails, sunglasses that another dear friend bough for me). The whole outfit was perfectly retro.

We walked along the corridor (we were on the third floor) and got to the lift. My heart was pounding against my bra, another sensation that was both delightful and terrifying) and when the lift came I stepped into as quickly as I could. When the door opened at the bottom and I stepped out into the luxurious ground floor there was a member of staff of the Grand stood waiting for the lift.

His eyes lit up and he said ‘Goodwood?’ and my heart soared.

Pictured – such a gorgeous dress. Thos eheels were perfect; I had no pain in my feet all day. Just a retro-obsessed woman in the warm sunlight of a September afternoon in an English field. But to me the culmination of all of my retro fantasies.

It took about an hour for the chauffeur to taxi us to the site. The weather was perfect but the organisation for parking and drop-off was hysterically amateur, and we found ourselves, handbags grasped, in a field a good distance from the site. For the first time in my life I faced walking on grass in heels and it was a hugely amusing situation. That field wanted my shoes more than I did. It took a while to work out how a woman needs to walk in that circumstance; you gingerly step toe-first and don’t put any weight on your heel.

It felt delightful. The warm sun on my made-up face, the feel of my tea dress lightly whipping around my tights in the gentle wind. We got to the gate, in a queue with a lot of people, and no-one laughed, no-one pointed. In fact it wasn’t long before the complements started and those were like a balm for my soul. When a woman fully made up and dressed as a 1940’s nurse tells you how wonderful you look with a smile wider than my own you can’t describe how good that feels.

We had forked out for hospitality so we made our way over to ‘the mess’, where the majority of selfies I took were taken.

Pictured – I looked at this shot and my first thought was ‘there’s another woman stood behind me’. That thought filled me with joy. ‘Another’ woman.

I didn’t take many photos; I don’t regret that, I was having a joyous time sitting with my legs gently together, stiff back, proper 1940’s pose, and just being there, amongst hundred of other people, was wonderful. I thought I’d be screaming inside, but I wasn’t.

I started to experience something I’d never experience before. I’ve talked about this occasionally, but this was much different. If I put on a dress and don’t immediately take it off, after time it feels normal. That’s too small a description; I get a warm feeling from the idea of wearing a dress but something changes in my mind. It feels ‘right’. In fact the dress starts to take control of me; I feel like a woman, I feel normal, I feel right. I feel one with the clothes. At Goodwood I spent the longest time I have spent fully enfemme and by the end of the day I wasn’t getting the ‘I need to get this all off and hide back behind my male personality’. I was getting, slightly disturbing, the ‘why can’t I be this way all the time?’. The dress was so comfortable, I knew I looked good and I loved the attention I was getting. The second glances, the smiles that weren’t mocking.

We went up onto the stands outside the Mess and watched a race involving 1960’s Formula One cars. I’m a Formula One fanatic but as I stood there, alongside men dressed in uniforms, mechanic outfits, I realised I was ‘one of the girls’. I had a glass of red wine held delicately in one hand and the noise of the cars made me put my fingers, replete with dark wine nails, over my ears. It must have looked wonderful.

We walked around the enclosure, went to the shops, admired the 1940’s aircraft. We got some wonderful complements including a lovely chat with a mother who had a trans child. She couldn’t stop enthusing over how good we looked and that was all I needed to hear.

It came to six o’clock and we trudged (delicately and in a feminine way, of course) back to the where the chauffeur was waiting for us. I took some selfies in the car and they were probably some of the nicest pictures I’ve ever seen; two excited housewives heading back from the event. Our faces are completely happy.

Pictured – just two retro housewives on a day out. Squee doesn’t start to describe how I feel about this picture.

I have very few complaints about the day. The only real one is that there were actually very few women who had gone the whole hog when it came to outfits; I’d say it was one-in-fifteen women in costume, the rest in jeans and t-shirts. If course, I may have become somewhat of a snob given I’d carefully selected all of my outfit to be authentic.

And that was that. We got back to the hotel and I was buzzing in a way I’ve never buzzed before. Took off the makeup, which made me feel a little sad, grabbed some room service and headed back through the mourning streets of London the next day.

Pictured – before the makeup came off. I just needed to get a picture of how bloody happy I was

It was a bucket list experience and I cannot thank my friend enough for suggesting, organising and putting up with me. She looked radiant and it was an honour to be there with her.

Would I do it again? Probably not; it was perfection and I wouldn’t want to try it again and not get the same level of joy from it. Will I spend more time out and about? Well, that’s the question isn’t it. I broke a lot of boundaries last Saturday, ones I thought I’d never be brave enough to do, and once I was doing it it was easy. That’s an eye-opener.

Stay beautiful and if you get a chance to live your dream, go for it. I did and it was wonderful to be Mrs Sarah Lewis, 1940’s housewife, out there in the real world, albeit just for eight hours……

Pictured – no filters, no edits. Just a 1940’s housewife in the bright sunshine. What an experience.

11 thoughts on “[Fashion] Good Lord, Goodwood….

  1. It was a giggle, wasn’t it? Lovely to spend time together. Shame I never bagged myself an RAF pilot or race car driver but that aside, a perfect day. Thank you for being brave enough to live your dream πŸ₯°

    Liked by 2 people

  2. Congrats Sarah !
    You did something with you female side and enjoyed a fem day out in retro land !
    There are many other retro events all over the UK and most are just as good fun as Goodwood, but not so expensive, so you may have an opportunity to try another such venue in the future.
    The issues with shoes and the wind are things that we can’t learn from a book, you have to experience them and work things out for yourself. Its all part of the fem learning curve !
    glad you had a good time and hope that you may have many others
    Onward and Upward

    Liked by 1 person

  3. Oh how wonderful is this Sarah?! 😊😁 XXXX
    You know when I first read that you were doing this I had a little squee inside! 😊
    I knew that you would be nervous (who wouldn’t?!) but I think that you were also incredibly brave too sweetie. It is a big, a huge step and in heels too! πŸ˜‰
    I am so proud of you Sarah! This is an amazing achievement! And I am very glad that you had the wonderful Stephanie to be there with you too.
    She is an amazing girl with I think, enough confidence for all of us. ☺️ I think that without her encouragement you may never have done this. πŸ™‚
    I think that she has shown you that being *this far* out of your comfort zone isn’t actually that uncomfortable. πŸ€”πŸ™‚ XXX
    And what else can I say but how absolutely gorgeous you looked! 😍 So feminine and womanly and sooo 1940’s!!! 😍☺️ The dress, accessories, makeup and hair were perfect! You were the epitome of vintage femininity sweetie! So totally in the era! 😊 XXX
    And while I know you said that you probably wouldn’t go again, I think that if Stephanie asked you you may struggle to say no. πŸ™‚ πŸ˜‰XXX
    So I’m wondering what is next for you? πŸ€”
    I still think a chaperoned shopping trip ‘up West’ with Cindy would do wonders for your confidence! πŸ˜ŠπŸ˜‰πŸ˜˜ XXX
    I can imagine that you’re still feeling a bit light headed about the whole experience but I hope that you will look back on it as an amazing achievement and a big milestone. πŸ™‚
    Take care my wonderful, dear friend. πŸ™‚ 😘


    Liked by 1 person

  4. Looked amazing. I was there (in drab unfortunately) on Friday and there were definitely a lot more ladies in costume. Glad you had a great day (very jealousπŸ˜ƒ!)

    Liked by 1 person

  5. Well done Sarah, I’m so pleased for you. It seems like you had the best time ever. Maybe you should try some more trips out. It’s just the biggest buzz ever. πŸ’‹

    Liked by 1 person

  6. What an amazing and uplifting post. Thank you for sharing this and congratulations on pushing through the fear. All the planning and effort paid off: how can did you both look!

    How cool to hear about the acceptance of the public and I hope the joy you felt lasts and lasts.

    Liked by 1 person

  7. Oh Sarah, I am almost tearful with delight at reading of your adventure. My tvchix sub-title is “gender prevarication graduate” so I completely understand what a step you took and the sleeplessness of the night before and the door clicking behind you.

    And the β€˜why can’t I be this way all the time?’ resonated with me so-o-o-o much. Currently dressed in ‘business lady mode’ for another working week hidden by Zoom video being switched off, that thought is with me all the time. I may have to change back later this afternoon and I am really struggling with it.

    “Nobody needs to be ashamed of being pretty!”

    Liked by 1 person

  8. I’ve known that feeling of dread going out en-femme to an event, that mix of fear, adrenaline, and excitement all poured into one, but it is oh so worth it!

    I was speaking to a Cis fem friend the other day, who commented that I looked so happy and relaxed in photos taken of me at Sparkle, and I was! If you’ve not been, I thoroughly recommend Sparkle as a way of getting out in a welcoming environment.

    I’d love to be Steffi more than I am, but even after all the years I’ve been doing this, the thing that still holds me back is my lack of self-confidence.

    You always look fabulous, hopefully this trip may tempt Sarah out into the “Big Blue Room” a little more.

    Liked by 1 person

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