Lovely question – thankyou!
My ideal outfits have nothing to do with attempting to pass, and everything to do with looking “right”, and reflecting how I feel.
There’s no real logic, and maybe I just haven’t got a handle on my own psychological motivations, but if an outfit is wrong for the moment, I know instantly.
I am planning a short break in Portsmouth, so will pack a couple of swimsuits for the hotel spa – in order to wear the right one, but only one nightie, as I already know which one I want to sleep in next!
For daytime, I will want a selection of outfits:
1. Travelling. Since I will need to stop at a services, the travelling outfit will likely be a skirt/top combo, the skirt being at least calf length, with either white trainers or ankle boots.
2. Morning meanderings: I might keep the same outfit for shopping and coffee – it’s an easy one to slip into and out of in clothes shops – but equally, a nice stretchy zip-free knee length dress would be ideal. This is my first test of how welcoming the shops in Portsmouth are of folk like us, and I will be noting carefully the helpful vs unhelpful establishments.
3. Afternoon delight. It’s likely to be cold and blustery, so a decent raincoat and umbrella, and a change from the morning outfit, after check-in. I like my imagination to take me places – but not too far, so, for somewhere like Portsmouth, with its long and distinguished Naval history, something resembling a Naval officers’ uniform seems appropriate and fun – a white, knee length, smart skirt, stripy blouse and blazer – that sort of thing.
4. Maybe an evening outfit before the main event, if there’s time, what with bathing, make up, dinner, etc. but the main dress is always something covered in sequins.
So that’s one example!
To address the question directly, I gravitate towards pretty dresses, short are fun, and I love them, but the cooler weather makes them impractical considering the age I’m presenting, and the tendency of seaside destinations to be somewhat blowy.
So something sensible – but fun – and usually stretchy, as my shape seems to be fluctuating, and definitely knee length unless I’m going out, in which case, I know that I will be noticed because of my height and presentation, so I will give people something to notice!!!