What to wear when 40+ and you look like everyone’s boring mother (work night out)

[Greenlittlegrasshopper]

I’m 40 and the eldest of my team of 5, although there are two in their mid late 30s and then three in late 20s / early 30s.

They are also all above averagely attractive women.

then there’s me 😭😭😭
I’m a size 8 but I’m not toned so my figure is poor and I think I look much bigger. My hair is nondescript and a bit rubbish. I’m only 5ft 5 so not that tall so struggle to pull some stuff off. Bust is small. Face is hideous.
I feel so awful about how I look at the moment it’s making me reluctant to go.

if I do go what on earth can I wear? It’s just a night out, meal and then drinks. Probably dressier than jeans but not like super dressy.

Budget of about £250 all in. I have no idea. I am so tired of looking like the old ugly granny in the corner 🤣

I’m 40 and never go wrong with straight leg black jeans, heels and a nice top. For Xmas I usually wear like a long sleeved one shoulder top, maybe with a bit of sparkle, so I’m still comfortable but dressy.

If you have longish hair, a nice bouncy blow dry is good and I always put a bit of fake tan on the night before for a nice glow..I know it’s not for everyone but it makes me feel nice with a bit of colour. I also use the natural strip lashes (again not for everyone) but makes me feel more dressy and glam than day to day.

I realise this is S and B. But in my experience, people- even young people- are not actively invested in judging you for what you wear. It's what you say, how you behave, what you do. To imagine that everyone is judging you for your untoned body is really dangerous. You can't defy aging.

I thought that too. Everyone's different. All the make up/ manicure/ blow drys are too much like hard work for me too.

I'm the same age but a an inch taller and pushing a size 10 now (also super flabby so I know what you mean.

I'm wearing a red leopard print satin mini dress from ASDA with tights and black ankle boots for mine.

Spend that £250 on therapy and start afresh next year.

Very true.

Have your hair and make up done professionally and buy a dress in the sale. You'll look fabulous. Go for the smoky eye. Every one seems to look glamorously done with a smoky eye.

Sounds like a self esteem issue more than anything else.

You describe yourself very negatively - giving the impression you're so much older than the others but if the 'next oldest' is in their late 30s, that's, what, 2 years difference? And you say the youngest 2 are late twenties early thirties - so does that actually means only one of the group is in their twenties, or that you don't know their ages? It's just an odd way of describing things.
Similarly 5'5 isn't "very tall" but is actually taller than average for women in the UK, and S8 is slim, toned or not.

£250 is a lot to spend on an outfit and there isn't any outfit on earth that will make you feel better about yourself if you're that self-conscious. I agree with the pp that you'd be better off spending it on a decent haircut and colour, which will last longer, and possibly a make up tutorial. Clothes are neither here nor there - someone confident and good looking could rock up in a £10 second hand plain jeans and t shirt combo and look better than someone who had spent hundreds on their outfit.

I'd check what the others are wearing as well - spending £250 on a fancy dress and heels and they turn up in jeans and trainers will only make you feel more out of it.

Thank you for all your suggestions!
im wondering about the sezanne top - not in velvet - and some jeans and a nice belt.

Dresses and heels aren’t really my style - I actually rarely see anyone out in heels these days.

Im seeing if I can lose another 4 or 5lbs which I think might help.
I think I was a 4/10 in my youth but now I’m like a 2/10 because I’m old as well. I know it’s vain but I just feel so horrible even leaving the house at the moment and I 100% couldn’t be in a photo or anything. I feel so
self conscious even though I know logically no one even notices me. And of course looks aren’t everything. They help though! I don’t want to be beautiful, average would be fine.

Nobody is rating you on a scale.
You are not old.
Or overweight.

Get some therapy. Your update makes me even sadder.

It's made me sadder too. Jesus you're in your 40s. Start investing in yourself. Go for a facial and a massage. Get your brows done and a manicure. Start eating better food, get out in the fresh air. You have so much experience to share with these younger women. Hope you have a great time.

Think you took it a little too far, @Greenlittlegrasshopper …

There are lots of gorgeous clothes out there but this Tu velvet jacket looks good with lots of things including black jeans or over a jumpsuit.

tuclothing.sainsburys.co.uk/product/tuc144652665?istCompanyId=07cf3c1d-7207-477f-aab0-212732e114dd&istFeedId=03391e81-6312-4095-9322-96087f0115ae&istItemId=mqpxqqrli&istBid=t&cmpid=cpc&src=Google&med=Shopping&utm_source=Google&utm_medium=cpc&utm_campaign=21432902788&utm_term=tuc144652665&utm_content=shopping&utm_custom1=164631095192&utm_custom2=825-875-8916&gad_source=1&gbraid=0AAAAADCAkB_Tbp6f6xGh6bSKEL_nQrmDz&gclid=Cj0KCQiAgdC6BhCgARIsAPWNWH1V1iT48fqgt90OuyFORJ-wcZ-t5UANLBno6QAgZd17kimB32KV64kaAr6QEALw_wcB&gclsrc=aw.ds

I saw my manager at a meeting in slingback heels the other day (and at pub afterwards) so I think they are back.

I hope most people aren't judgemental enough to think of an older woman as the "old ugly granny in the corner" or "boring mother".
Wanting to look your best is good. Describing other women like that is completely unnecessary.

I have this jumper in black and navy and it’s always looked good, in fact it’s solved what I’m wearing on Monday for drinks with ex colleagues:-

www.whistles.com/product/annie-sparkle-knit-30429.html

how about looking at all the positives, at only 40 and only a few years older than some of the other team members you are very far from being old.

5ft 5 while not being tall is certainly not short
Size 8 is really slender, you say you are "not toned" but given that we are in in the depths of winter it is not very likely you will be showing a lot of skin.
I do empathise with how you feel about your appearance though, we are bombarded with images of perfection and fed unrealistically beauty standards. It can eat away at our self esteem . I hope you find something you like and even more than that I hope you have a great night out

I woukd go completely opposite of what everyone says and spend no money on clothes

just wear something you already own that looks nice and you feel comfy in

wash your hairs, style it, put some make up on, wear your moves blingest earrings

Now for the long term you need to address this negative feeling you have about yourself and maybe doen that money, and some time and effort, into finding out what makes you happy and feel good about yourself and then DO THAT 💃

find your spark, whatever it is that gives you joy, and run with that.

i found a new hobby in my 40s that has got me loads of new friends , and fun, and made me grateful for my body instead of looking at its perceived flaws

Possibly the OP won’t return - but here’s what everyone’s boring mother should be wearing next spring. Gloriously un-ingratiating models and the definitive answer to Am I too old to wear …?

https://petarpetrov.com/collection/spring-summer-2025

@MistletoeRegrets I love the first jacket minus the bread rolls 😄

I actually love a lot of those clothes but god what’s with the fruit and veg shoved everywhere. 😂

Wow. If you are real then you need to work on your self esteem.

Oh … Clearly I didn’t make my point comprehensible enough. It was the models wearing the clothes that I was focussed on - with reference to the title and OP of this thread.

Gloriously un-ingratiating models

I love gloriously un-ingratiating models. They're far more effective in selling me something than smiley , posey ones.

Oof! I'd love to have legs like that