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.

Black skinny jeans, converse/heeled boots and a nice blouse with a black leather biker jacket is my go to.

Mom jeans (I love primark’s- £15)
Chelsea boots, or a nice pair of trainers
A plain top with a little detail, like a lettuce trim or a sweetheart neckline
Pretty earrings, maybe some layered necklaces

How fat?

Could you do black skinny jeans with a denim or leather jacket? A little pair of boots and maybe a scarf?

Ooh, I don't think skinny jeans look good on me, very fat legs and cankles.

I usually wear a size 18-20.

Have you considered jumpsuits with a belt?

The 2000s are back so maybe jeans and a nice top? I like wide leg jeans at the moment.

I was about to say black jeans and biker jacket too

Ah ok! Then I'd swap out the skinny's for some mom jeans with a denim jacket and scarf?

Pick 1 item from your wardrobe that you are happy with and shop around that one item. I find if i wear an all new outfit i feel a bit like i'm wearing a costume.
Have a look on instagram and find some one who is a similar shape to you for inspiration, take some screenshots, then start shopping.
You might have to step away from Asos, i'm finding less and less on there. Good luck OP x

I was going to say wide trousers but I think a dress might be easier as it's just one thing. Maybe a midi dress.

There are 2000 midi dresses on Asos in an 18! Sometimes Asos isn't good as there is too much stuff!

I'm the same shape OP, I've just discovered Asda's maternity range fits me perfectly! Today bought a nice black and white long shirt dress which has a collar so looks a bit smarter. Will wear with converse and denim jacket.

I am the same shape. How tall are you? I wear cropped wide leg jeans with black boots or trainers - I have various tops in different styles that go with the look

Pick 1 item from your wardrobe that you are happy with

It's beers and a pizza. Unless you usually spend your entire life in a hermit's cave in the Outer Hebrides clad in home- spun flax and this restaurant has the sort of dress code The Ritz has, any, normal, everyday outfit will be fine. Slightly more scrubbed jewelry and/or accessory wise than what you'd wear for going to the pub/ meeting a friend. You're going to be sitting down most of the time anyway.

Chunky boots, jeans in any style other than skinny, blouse, leather jacket. Maybe some nice earrings or jewellery. But casual definitely.

Do you have a longish dress you can wear with trainers?

Wide leg trousers, cord or jeans are nice with a top and trainers?

I would wear a short but floaty black dress with black tights, block heeled ankle boots and a colourful big fur coat! Maybe a tiger print fur coat! Or a bright blue or pink one.

Jersey maxi dress, trainers, oversized blazer.

Boot cut jeans to balance your shape out, floaty blouse that has a v neck, boots and Nice make up.

When you say a very trendy restaurant - trendy in what way? Is there an actual dress code? Will there be drinks/club/anything else afterwards?

I lean towards casual when I'm out unless dress code stipulates otherwise. Off the top of my head from what's in my wardrobe, I'd probably wear grey mum jeans or blue cropped wide leg jeans, a black and white thin striped jersey top with a slash neck, chunky boots like my Frankas from All Saints (similar available everywhere in every budget), leather jacket, and maybe a coloured bag (I have a coral coloured small leather cross body bag I'd probably reach for).

If something a bit smarter was required I'd go for cigarette pants or smarter jeans, oversized blazer, brogues, probably plain silky shell top.

I'd wear a midi skirt, black fitted 3/4 length tshirt and black ankle boots with my leather jacket. I'm a size 18 and 5ft

Thanks everyone, I appreciate the advice.

I have no idea what suits me these days, my entire wardrobe consists of work uniform (navy suit, striped shirt), exercise clothes, one dress I always wear and one pair of jeans. I've lost 4 stone recently so nothing fits properly. I just want to feel nice for a while.

There's no dress code but looking at instagram it seems like most people get a bit dressed up. It's like the Cool Place To Be Seen. There will probably be drinks afterwards but I probably won't go.

Fair point that I will be sat down most of the time but there will be lots of pictures taken and for once I don't want to be the fun sponge that refuses to have her picture taken!

I like these three looks - maybe a biker jacket instead of the denim one, opaques with the shorter dress?

@HelloDulling

Jersey maxi dress, trainers, oversized blazer.

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

@WannaBeCool i think its lovely that you want to make an effort. Are you pleased you lost 4 stone? You probably need to go and try stuff on. Are you assuming a size 18/20 or is that your old size. I once lost 4 stone and didn't feel different at all but I'd gone from a size 16 to a size 10/12 and was amazed when I actually tried stuff on so my advice is to try stuff on in shops rather than looking online.