Need an outfit that's cool but relaxed ?!

[WannaBeCool]

I'm the least stylish person ever but I have been invited out for beers and pizza at a very trendy restaurant with colleagues who are all early 20's, very beautiful and stylish.

I'm fat, apple-shaped but with thick legs, short and in my 30's. I've been scrolling on ASOS for ages but I have no idea where to begin!

Please help? I want to look well put together but still feel comfortable.

Don’t base much on Instagram - the place will be picking the images to present themselves in a certain way so the pics may or may not representative of what people actually wear.

Don’t overthink it. In the nicest way, they’ve invited you for your company not your wardrobe.

Well done on losing 4 stone - that’s amazing. If nothing fits you properly at the moment, what would be something you’d really like to fit, regardless of this evening? Jeans (wide straight leg are good) or a top you’d enjoy wearing? How would you like to look?

I really like styled by Danielle on Instagram at the moment

I have fat legs and cankles and I wouldn't go for any cropped type trousers because for me they draw attention to the worst part of my body. The last place I want people to look is at my legs! Luckily these days there seems to be every style of jeans available, I wear boyfriend or mom or bootcut.

I'd wear jeans and chunky boots and a biker jacket, then look for a top that's going to fit with the cool vibe (I'd look on Asos for that, or at some insta accounts first to get some ideas).

I've ordered some mom jeans, a wrap top, a t-shirt, a loose fit blazer, some trainers, some flat shoes, a new bag and also a shirt dress which maybe isn't trendy but I liked.

I have a leather jacket, several pairs of dr martens, a structured blazer and some jewellery already.

Hopefully enough of it will fit properly (and I'll like it) that I can put a decent outfit together.

@WannaBeCool

I've ordered some mom jeans, a wrap top, a t-shirt, a loose fit blazer, some trainers, some flat shoes, a new bag and also a shirt dress which maybe isn't trendy but I liked.

I have a leather jacket, several pairs of dr martens, a structured blazer and some jewellery already.

Hopefully enough of it will fit properly (and I'll like it) that I can put a decent outfit together.

Sounds fab! Come back and share when they come.

Huh? This doesn't sound this stylish at all!

No? Okay, I guess we can’t all like the same things.

Well, the picture above is a damn site more stylish (and comfortable) than skinny jeans that’s for sure. I would also look at the weather report for the night you’re going because it’s 20 degrees in London tomorrow and you don’t want to be hot and sweaty if it’s similar temperatures where you’re going.

@HelloDulling

Huh? This doesn't sound this stylish at all!

No? Okay, I guess we can’t all like the same things.

I love that look but I am too short and rotund to pull it off!

@HelloDulling That's not a jersey dress though?

I am coming up for 40, getting rounder thanks to the menopause and a size 16/18 - my go to outfits for casual dinner/drinks are:

Shirt dress, belt, chunky flat boots and either biker or denim jacket.

Wide leg jeans, white blouse shirt, heeled boots and blazer.

Wide leg jeans, blouse, trainers and blazer.

Overall style jumpsuit with a nipped in waist and heels.

Enjoy your night out!

@HelloDulling

Huh? This doesn't sound this stylish at all!

No? Okay, I guess we can’t all like the same things.

I want this entire outfit thankyouplease.

@WannaBeCool

Just popping in to say that I'm about the same shape and size as you and you can where whatever you like, don't worry about whether other people will look at your ankles.

If it helps, I bought a really nice handmade black linen dress (from thepeopleshop) and then I change that a lot with extras. Sometimes tights and boots and a jacket, sometimes heels, sometimes a long sleeve underneath with trainers, sometimes just Birkenstocks and a cardigan. You can get similar from House of Flint, their basics shifts are really good and you can customise the lengths. Get a good piece that fits you and you love and then add to it with fripperies. Game changer.

I like the idea of a shirt dress @WannaBeCool, with your chunky boots.

As the 90s are back in you could also do a floral short dress/skirt with boots and your leather jacket or a wrap crop cardigan which is flattering and creates a waist. Or a cami dress over a t shirt with boots

@HelloDulling

Huh? This doesn't sound this stylish at all!

No? Okay, I guess we can’t all like the same things.

Oh man I want that outfit ! Especially those sunglasses - do you have a link?

@HelloDulling

Huh? This doesn't sound this stylish at all!

No? Okay, I guess we can’t all like the same things.

It says "I've got no imagination but I'm trying (too) hard to be Alexa Chung" to me.

I'm a dress and docs person for pretty much anything. So whatever dress you love with docs and you are good to go. Nice jewellery and bag and hair and make up done and you'll be perfect. The whole going out vibe seems to be much more casual now. I went our for dinner on Saturday at a trendy restaurant wearing a jumpsuit with trainers, I'd never have dreamt of going out in trainer pre covid but it seems like everyone just wants comfort now! I think more casual is trendier than too dressed up and try hard