Dress shamed on dates

[rubberduck68]

I am mid-fifties and OLD. I have been on the receiving end of a comments about how I dress, all implying that I am not dressed up enough. I like jeans, and trousers. I wear good quality ones, on trend (or so my daughter tells me!), good tops, nice jackets, I'm a trainers and Chelsea Boots fan, don't do heels. Own one smart black dress, wore it for a funeral two years ago, and have a couple of summer ones that I pull out when it's scorching. Last night went to Bills for dinner. Bills is low-key, it's a chain, we ate burgers, I wore good jeans, a vintage Bella Freud jumper, some boots, hair and make-up effort was applied. He said, "I thought we'd be dressing up." This has happened to me a fair bit since OLD, never happened when I was younger and dressed the same. Is it just men of this age who expect women to show up in high heels and skirts/dresses? We had a polite debate about it, and he asked me what I'd wear if he took me (I know, I know) to a wedding, and I replied that the last wedding I went to I wore a fitted waistcoat with nothing underneath, wide legged linen trousers, and lots of cool jewellery and got loads of compliments. He pulled a face. A face!! Anyone else dress shamed on dates? Is it their age? Am I out of touch with what to wear on dates? Brutal honesty welcome!

Wearing stylish boots instead of trainers is dressing up.......... surely??

They are showing up in smart shirts and trousers, where as I'd rather date a man in good jeans and trainers,

Maybe that's how you filter them out by saying something like that in your profile.

I'm similar age and dress like you. Some of my peers dress more "up" and it feels old fashioned to me.

I think that ages them tbh.

I don't know that is an age thing tbh, but a personality thing.

Lots of us in our 60s were once punks, goths, new Romantics etc and still don't dress conservatively or at least dress casually in things like jeans, boots, trainers etc. much like younger people.

Others in their 60s will always have dressed conservatively and think they have to dress up to go out to eat etc.

He's employing this nasty tactic - 'negging' - little insults to deflate your self esteem so that you are grateful he's with you.

Dictionary
Definitions from Oxford Languages · Learn more

neg
/nɛɡ/
informal
verb
gerund or present participle: negging
insult or undermine (someone) in the belief that diminished self-confidence will make them more receptive to sexual advances.
"his seduction technique seems to be to neg her into submission"

So I'm guessing men you are dating are in the right age group to be ex punk, new romantic or heavy metal fans, and should expect you to be the same. Jeans wearers since forever. It looks like, as always, they just think they have the right to pass judgement on women.
Correct response is the traditional two fingered salute in his face.

He probably wanted you to wear something sexy and feminine, rather than stylish and casual. I doubt it was really about dressing up smartly.

Weird. I've never had this. Am in 40s and dated men in their 50s. But I'd never go for a suits guy and I don't think a man who'd want a dress up doll on his arm would go for me.

I turn up in all sorts and often wear my man repeller clumpy boots on dates. Would never wear heels. Hasn't put anyone off so far. But then I'm choosing men whose look I like too.

The right man won't complain.

My sister always met her husband to be in her riding clothes for the first few weeks of their meeting up and when he came to take her out on a 'proper' date at a function and she walked in wearing a dress, her hair up, heels and jewellery he was lost for words he was so smitten. It was a lovely moment. He's still smitten with her, decades later.

Sandee!!!

I think it's a certain type of man - too many in the world. They probably have an idea of what a 'sexy woman' looks like and it's not jeans. They're a bit insecure and think if you don't 'dress up' you're not into then because you haven't 'made an effort'. I think weeding them out early is a blessing.

Perhaps you need more of a Guardian reader!

I hate to break it to you, but men ARE more visual, it isn´t some conspiracy theory. We also have EYES, but we also attach more importance to certain qualities that can´t be seen with the eyes.
As to rude fuckers, I agree with you. A gentleman shouldn´t comment on a lady´s outfit if it isn´t positive.

I wonder if these men are watching Love Island/reality TV and have normalised the way the women are styled on those shows? Similar to assuming every sex encounter should be porn. I agree with others that this seems a very useful tool to filter out the tools.

The OP is in her 50s. We grew up in the 90s not the 1950s.

I'm in my 30s and I think it can be frustrating when you make an effort and the other person doesn't.

DP hates wearing shirts and I find it annoying if we're going out for a special occasion and he rocks up in jumper. I think it's just manners and respect for the other person to show that you've made the effort.

Having said that, I wouldn't be fussed about what he wore on a first date to a chain restaurant. However they might see it as an indication that you're never going to make the effort. I think there's midway point between a dress and heals, and jeans and a jumper.

Jesus Christ, it's Bill's, not the bloody Ritz! Another reason for me to never do OLD. I never wear skirts or dresses. Seems the men will be disappointed 🙄

However you're dressed, it's incredibly rude to tell your date that you don't like their clothes, and guarantees that a second date will not be forthcoming!

It may have happened three times, but it's definitely not you.

Yes I was a punk! Well, post punk! I wore an original Sex Pistols T-Shirt under a boyfriend tweed jacket to one date and we bonded over music, wore it to another one and got a look and asked if it was my daughter's, which makes no sense whatsoever (I am mid-fifties) and told me they were musically clueless. I also wear a very long fringe and dark eye make-up, a bit Chrissie Hynde and that's been commented on, e.g. you should trim that, or is that in your eyes? blah blah blah. The men who look aesthetically interesting to me on OLD are very thin on the ground on the apps, and often they just don't match with me, which is very disappointing.

How old are the men you're dating? A 45-50 yo will have different expectations to a 70 yo who only chose you as you're a younger 'hotter' woman.

'The men who look aesthetically interesting to me on OLD are very thin on the ground on the apps, and often they just don't match with me, which is very disappointing.'

I sympathise op. Same here.

Blimey that’s just rude. I’d not comment on what the guy was wearing (unless I really liked his shirt or whatever). We are all adults here - if he was turning up in clothes I didn’t like and it was more than say, a first date, I’d likely fade him out, I certainly wouldn’t try and dress him!

I worry that the "midway point" is me changing myself to accommodate a man who I don't even know yet; surely that's a slippery slope...

This is what I think too.

I have my age filter set from 50-62

They want you to look sexy for them so you look 'good' on their arm.

Stuff them! Keep being your authentic self and hold out for a man who really appreciates who you are, including your style.

I used to date on Guardian Soulmates, and the men were all quite cool dressers, and I never got any insults... sigh... Hinge and Bumble could learn a thing or two from that.

Maybe try dating someone who works in the trades and not an office worker