Clothes for middle aged dating?!

[Escapetothecountryplease]

I have jumped back into the world of dating at age 43 and having a pretty nice time meeting various men off an app for ☕ and a chat. So far so safe.
Most of the time it's just a case of hmmm not for me.. however I have just excitingly had a second date ( although ultimately decided not to go any further) and as it was an evening out have found myself with a massive gap in my wardrobe!!
I've been chronically unwell for several years, gained weight, binned all the old clothes, plus I'm single mum to 2 kids with special needs so I have had precious little time or energy for evenings out. But I'm getting more and more well and keen to get out a bit more.

I'm now a size 18, 5'8 , boobs 38DD but I'm broad shouldered and I don't think I look especially fat. I wear significant orthotics so it's always trainers, and also need knee high compression socks so I find my daily clothes are generally wide legged jeans, or other wide legged trousers with either a jumper or a t shirt with a shirt over it. I can do daytime smart casual pretty well with nice gold jewellery, a french tuck and a belt. Maybe a scarf or headscarf. Evening wear however I'm pretty stumped!! Tonight I wore the same jeans with a Love and Roses black lacey blouse - which I bought for a Halloween day of the dead costume!! It's quite nice but doesn't feel very me.

I tend not to wear black, I'm blonde and wear a lot of navy blue, and spring/ autumn colours, coral pink is my favourite. I'm not wearing loads of prints atm, but have in the past and certainly not averse. I seem to have a lot of t-shirts that are white with a navy stripe 🙄 I live in a small country town and the vibe is definitely more casual. But I really dislike the Joules sort of look.. I went to art college and used to wear lots of vintage stuff, but I feel I've lost all that edginess! Clothes are pretty plain..

I had a couple of summer evening dates before and felt nice enough in a t-shirt and casual blazer - but those I have are very lightweight, and I'm more comfortable in something fairly unstructured. I quite like the look of something tucked in with a layer on top, I think it's quite slimming. I also find a batwingy sort of shape quite flattering.

Can anyone please suggest me a couple of eveningy tops/ sweaters ideally warmish atm. A bit sexy / glam but not too OTT . If poss under £50 , or something I might be able to find on vinted , I'd rather have a couple of things to choose from depending on my mood.

Thank you!!

I’ve had a few glam evening shirts from Anthropologie, there are still a few in the sale.
I also bought a glittery v neck jumper from Live Unlimited, I wear it loose but it would look ok tucked in.
Ive been thinking about a velvet jacket, Claudia has been wearing them on Traitors, and they do upgrade a plain T-shirt and jeans very nicely, plus warmer than a shirt!

Are you dead set against dresses? I'm not suggesting you turn up in a ballgown, but even a fairly casual dress would be suitable for most evening dates in the small town I live in. Dresses can be fun because they let you play around with shape and structure if you're arty and into fashion.

Thanks @CakeIsNotAvailable I used to live in dresses, and have quite a lot -but unfortunately it's the footwear and horrible medical socks I had to wear that hold me back from them . I reckon once I got to know someone I could experiment with dresses but the stockings would be visible and I'm not that much at ease with them for first dates. I can't go without them or I get all dizzy and feel faint..

@DelphiniumBlue good idea about a velvet jacket.. and I'll 😁 have a look anthropologie

@Escapetothecountryplease does this asymmetric sweater work for you? It’s batwing and looks amazing on. Very chic but actually very practical.

https://jaki.co.uk/collections/asymmetric-draped-jumpers/products/new-asymmetric-draped-camel

Ignore the price. If you like it (in whatever colour), I can share where to buy the exact same sweater on Etsy for a fraction of the price (under £50). 😋

@HundredMilesAnHour please share as I rather like that shape!

@Notmydaughteryoubitch There are a couple of sellers but this is the one I’ve bought from and the jumper is identical (minus the ‘Jaki London’ label) and one third of the price:

https://www.etsy.com/uk/listing/1800434439/

If the link doesn’t work, search for ‘Italian asymmetrical viscose jumper’ and you should find them. Interesting how much mark-up Jaki London is making just by putting a label in the same sweaters!

I find my orthotics fit nicely into knee high boots if I go up a half size. They would cover the stockings too.

@RosesAndHellebores I'm afraid I cannot walk in anything other than trainers with my disability.. last thing I want is to be in pain and stumbling while meeting somebody new!!
If I ever manage to find a knee-high boot with a trainer type of sole in a wide fit, with a wide calf fit, I'd love that! But as I have chronic fatigue as well as everything else city centre high Street shopping trips are out and the cost of ( And extra energy of returning ) trying on failure boots at home is ridiculous. I have definitely tried in the past, But at this point I'm resigned to having a couple of pairs of trainers of various different levels of smartness, mostly with the same brand.

But thanks for your suggestion 👍