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?

Sorry I should’ve said - I’m 35 so don’t want to wear anything too trendy or frumpy, 5’9” and fairly slim.

Yep, wear what you feel good in. Big smile.

I'd check if the restaurant has a dress code first.

Personally, I'd rather dress up a bit more and not wear DMs.

I agree wear what makes you feel comfortable and confident in primarily however docs and a dress isn't a good look in a posh restaurant in my humble opinion.
There's plenty of nice flats about! Or heeled boots? I'm much steadier in my feet in them than stilettos.

But whatever you wear, no one will actually care and I'm sure you'll look lovely and dazzle them with your personality not your docs lol x

I’d wear a dress (a loose, sack-like one seems elegant atm) with either nice plain trainers or other flat shoes.

The dress code says smart casual, jeans are accepted but to be respectful that many diners may be celebrating a special event. So that’s clear as mud.

Any suggestions of flats that aren’t ballet shoes? Is there such a thing as a smart, flat boot?

Could I wear a smart(ish) Chelsea boot with tights and a dress? That’s sort of smart, isn’t it?

Something like this?

www.johnlewis.com/jigsaw-floral-stem-midi-dress-black/p5091174

Have you got DM shoes or the boots? Can you post something that you love so we can get a taste of your style?

Wear the DM's anyone who judges you for being comfortable and expressing your personal style when we're in the middle of a global pandemic needs to get a grip.

Have a fab time

I agree you should feel like you can express your own style but I think most people feel awkward if they feel underdressed or otherwise dressed inappropriately.

I’d see if you can see photos of diners at the restaurant eg from their social media pages. And maybe find out what your partner and family are wearing. I know others wouldn’t be, but I’d feel self conscious wearing DMs if everyone else was wearing elegant evening wear.

I think a compromise could be a flat smart boot and dress for example.

A nice ankle boot with a lovely dress and enjoy!!

Could I wear a smart(ish) Chelsea boot with tights and a dress? That’s sort of smart, isn’t it?

That’s exactly what I’d wear OP. Nice necklace or earrings too, if that’s your thing. Stand tall, big smile! Enjoy

You could absolutely wear flat chelsea boots, I tend to wear black ones with black tights. You can get a cheap pair if you don't think you'll wear them again. I find it easier to wear a knee length dress as I don't wear dresses often and I'm constantly pulling it down/checking it hasn't risen up if I wear a shorter one. Nice pair of earrings and you are sorted!

something like these with a dress or skirt?

I have a dress like this but a thicker material and a burgundy colour. With black tights an a pair of Jimmy Choo Youth boots could that pass as smart enough?

barnardblack I really don’t feel comfortable wearing heels at all. I’ve never worn them, I just wouldn’t feel like myself and I’d only ever wear them again when I have to meet someone else’s parents for the first time 😁. I really don’t do fashion, I just own a few things that I really like and have spent ages choosing. That probably makes me sound like a bit of a diva but I just get really self conscious if I’m not wearing something I specifically chose.

I think your DMs would be totally fine (And in any case they will mainly be under the table!) and look great with a frock and tights. I am a fan of dressing like yourself - I just tend to ramp up hair, makeup and jewellery to look more ‘done’.

Btw: I’m sure his family will just be really excited to meet you and totally focused on making you feel welcome and comfortable. Hope you have a great night!

I don't love the Jimmy Choo boots with it, i would be more inclined towards DM's but that's my personal view

I wore DM patent leather shoes (and a dress) for my “posh” meal out for my 40th. This was a London “destination” restaurant with celeb chef etc and to be honest most other people there were dressed up but in jeans. My regret about that outfit was the dress being too plain/severe and not feeling like myself. I should have gone for something more me.
I’m also pretty sure that the only person who cared about what I was wearing was me!

That dress is far too revealing for meeting the parents at a posh restaurant. The jimmy choo boots are borderline.

Do you have any black trousers you could wear with a satin/silk shirt and the Jimmy choo boots?

Ok so start with boots, especially if you feel comfortable in them
With those I'd go one of two ways

1. a longer dress or skirt (but I find dresses easier) possible with slot/buttons up the front.
2. skinny black jeans (not faded or ripped) or trousers, and then some kind of stinky top.

Remember you're at a table so people only see the top so for family dinner I'd avoid too much bare cleavage. A shirt style would work well you can work the buttons as low/high as you like

Yeah that dress wouldn't really be appropriate I don't think for a first time meeting the parents. It's also very summery and I can't see it working with tights and boots to be honest.

Chelsea boots and black tights would be fine. Something like this joanieclothing.com/joyce-daisy-print-frill-wrap-dress.html

Oh gosh not that dress. Far far too revealing for a nice dinner. Possibly even a 'faux pas'

Honestly jeans can be really smart. Ive just been to a Michelin starred restaurant in jeans, ankle boots, a lovely 'feature' sleeveless top and a white tailored jacket. This picture is not me (mores the pity) but similar to what I was wearing and I felt comfortable and stylish.
Last week I went to a 'posh' dinner wearing black skinny jeans and a white shirt and ballet flats

Flat ankle boots are de rigour at the minute so maybe them?

Missed picture

@DarkMutterings 'stinky top'