Posh date - what the hell do I wear?

[BuggeredItUpAgain]

I normally dress very casually and pretty much spend my life in jeans, t-shirts/ vests and trainers or DM’s. Occasionally if I’m going out out I’ll wear a dress with a leather jacket and trainers or DM’s.

I’ve been seeing a very lovely guy for a few months and he wants to take me to a very posh restaurant in a hotel with his parents, brother and SIL for his birthday. It will be my first time meeting any of them and I’d really like to make a good impression and ideally look like I’ve made a bit of an effort but without having made too much of an effort iyswim.

I don’t even know where to start looking or what the hell to wear at all. I definitely won’t/ can’t wear heels as I feel too self conscious. Can I get away with a dress and DM’s? If it’s a nice dress and I wear some jewellery and maybe a slightly smarter jacket than my normal leather jacket?

I know I hoped no one would notice

Sorry, it’s not that dress but it’s similar shape. Much thicker material and straps and definitely not see through in anyway, more of a cord material in a burgundy colour.

Otherwise I have a couple of fairly frumpy Fat Face dresses that I could wear or o have this Ralph Lauren dress which I wear for everything when I’m needed to be smart. Only problem is I trimmed my wardrobe right down over lockdown and now only have a denim jacket, leather jacket, Barbour jacket and a waterproof. The only one that looks slightly acceptable is my leather jacket but then I look like I’m going to a funeral. I could brighten it up a bit with some jewellery, I guess?

If you search for the restaurant’s name on Instagram under the places tab you’ll be able to see everyone else’s photos that have been tagged at the restaurant.
I find this really useful when assessing what to wear somewhere new

That Dress is great. Jewellery and/or scarf. Denim jacket will work well with that frock too. An ankle boot and bare legs will look beaut too.

But as PP have suggested, do look at pics of what others have worn on visits. I'll be honest I've visited huge amounts of Michelin starred restaurants in my time (granted most in London) and that would be a very 'dressy' dress for those places. I tend to go in my work outfit if it's a weekday or the Jean type outfit if weekend.

I'd be surprised if it's 'evening dress' unless it's some very very old school, provincial stuffed shirt restaurant.

Pic of what I was thinking

We can all advise on here until the cows come home. Personally, I would go for a dress with ballet flats.

But why not discuss this with your new friend? He will be more familiar with your wardrobe and, possibly, the place you are visiting

Enjoy yourself, it should be a fun occasion, not an endurance test.

The black dress and your leather sounds fine.
Is it a biker style jacket?

that dress looks fine. will go nicely with a biker jacket. I would wear trainers or DMs with it and not buy flats. That is akin to dressing up, I would not.

I’d go for the dress and the Jimmy Choo boots - not the docs - that will be a good look! maybe with statement earrings. You won’t need the jacket once you’re inside the hotel anyway so can take it off before you enter the restaurant.

Lunch or dinner at a ‘smart’ London restaurant would see me dressed similarly to the previous photo of jeans, heels and a jacket. I’d wear a ‘good’ sleeveless top that I would be happy to have on show when I removed the jacket. I may wear similar but with trousers (tapered or cigarette) in the evening to meet the parents.

I love dresses but mine are all too casual, fit and flare shirt dresses. In your shoes (or dms!) I'd wear my trendy smart trouser and blouse combo. I only own comfortable flats so I'd just choose the smartest of these.

The title of this thread reminded me of this funny song. It's in russian but subtitled in english.