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!

Totally a social class issue. Maybe it goes hand in hand with the stats that middles and above tend to stay married whereas those below tend to divorce more or have a string of partners. Therefore the men in their 40s,
50s and 60s on OLD tend to be from lower middle and below? It’s all very Hyacinth Bucket but there may be something in it!

Dead god it’s 2025 and men are still under the impression that women dress for their benefit.

I’d have no hope as I look like a sack of shite in skirts and only wear dresses to weddings or in the summer.

Oh dear OP, are you not performing pretty correctly for these princes? Next time do remember to parade your assets in something short and low cut if you want to win the prize 😂

FWIW OP, you sound gorgeous 😍

This. Except I’d stand up, do the pitying look, slow head shake and mutter “oh dear” then leave.
These men sound so shallow they’d drown in a puddle.

Sod them and their outdated ideas on how a 'sexy woman' should dress. Who wants to date a dinosaur anyway? Stay true to yourself OP, you sound awesome. The right man will 'get' your sense of style as part of who you are. Don't bother altering yourself for the benefit of a man who is not worthy. Think of it as a useful filter for knobheads.

You sound super stylish! I wear what I’m comfortable in on dates. I don’t own heels and rarely wear dresses, so if I wore a dress and/or heels I’d feel so awkward and probably come across as such.

Stock answer:
“oh fuck off we grew up with grunge and rave not little house on the fucking prairie. I know I look fine. Let’s leave this here. How much do I owe?”

It's an arsehole filter.

To a PP post upthread, what is this weird thing where people think you want their opinion on your appearance when it's not positive! I'm in my 30s and I only ever get it from men approaching 50 and above, my friends (all in their 30s or early 40s) ... well I doubt it would ever cross their minds to comment negatively, they would see it as hideously rude.

Also your style sounds great - only boring men will be annoyed or intimidated by your having great personal style, remember that.

@Mrsttcno1
But my nanna & granda are in their 60’s and my granda cannot accept that jeans/trousers etc are “dressed up” now. My nanna does wear them but he always comments that those should be clothes for doing the garden or walking the dog, not “dressy” clothes!
That's your nan and grand though.
I'm nearly in my 60s and dh definitely is in his 60s now! It's joggers for dog walking.

My mum and dad are in their 80s and they are jeans and trainers still!!
We dress up,of course, but not to a burger joint!

My friends, in their 60s, go OLD all wear jeans, currently wide leg ones and looking great on their dates. Ivevnot seen one dress up for an OLD so It's not generational or ageist.

When he said "I thought we'd be dressing up!" Did you reply "what - for this place??"
I would have said ' I am!' 😆

If I was to wear a dress on a date it would be my favourite knee one with opaque and my Doc marten mary Jane's until the summer whe it would be dress with my Fly London sandals!
These blokes need to bore off.

I suppose the chaff are weeding themselves out on the first date which is a positive!

It's odd behaviour and makes you wonder what their thought process is. Do they think so highly of themselves, that why wouldn't you change your wardrobe to impress them based on one brief meeting?

Can't you stick it in your profile somewhere that criticisms of dress on the date will not be tolerated. I don't get all this expectation stuff though. I also don't dress up as I don't feel comfy.

Neemie · Today 11:19
He probably wanted you to wear something sexy and feminine, rather than stylish and casual. I doubt it was really about dressing up smartly.

rubberduck68
I hear you re. them, but I think you can be all of those things without wearing a dress or skirt, but maybe a lot of men don't, well clearly some of them don't!

@rubberduck68 I agree with @Neemie OP - I don't think it's about wearing a dress or skirt necessarily, as women can definitely look sexy and feminine in jeans.
I think you could flex your look a little for a date, but still be comfortable that it reflects your own style. I saw The Pretenders at Portsmouth Guildhall in the early 80's and Chrissie Hynde looked amazing in black leather jeans, (not too high) heeled boots and a white frilled shirt under a pale grey cropped military jacket and from what you've posted about what you like, I don't think this look would be too alien to you. You could swap in your biker jacket and achieve that "tough/luxe" (or cool/sexy) look easily.
Personally, I think it's most important to dress appropriately for the occasion/venue so I would also have worn jeans to Bills too, but paired with heels and a feminine top (it's definitely not a "sexy" dress kind of place! 😳 ).
Incidentally, if you get any more negative comments about your attire from future dates, say nothing. Just silently, slowly and deliberately look them up and down ...😉

Hmmm, probably a bit against the grain here...

If DP suggested going out for a burger or pub lunch, I definitely wouldn't be expecting him to wear more than jeans, t-shirt & trainers (maybe a casual shirt), and I'd be wearing similar (jeans, trainers/boots, top/jumper).

But early dating, I'd have expected him to make the effort, so to speak. I don't see how it's any different the other way around. There's plenty of options between jeans/boots/jumper and heels/sexy dress.

Easy way to get around it though - When I was dating I'd simply drop a casual, "Ooh, what's the dress code?" into the conversation when making plans.

HNRTT but as a PP said, it sounds like a helpful, early signal.

If annoyed, perhaps try smiling indulgently, looking at his hair and frowning as if to see it it looks dyed then say how your grandparents often said something similar and you wonder if it's a generational preference...

Well I'm 60 and not a 'nana' yet and wear smart jeans and a top when I go out with some Prada loafers or Alexander McQueen trainers. I guess I'll have to add them to my gardening stuff now...oh wait...I hate gardening and will be going out In London tonight with my also 60+ husband.
Age is irrelevant. The guys OP is trying to date want her to wear a 'come and fuck me' dress and haven't moved on from the 80's and I expect they dress like it too.

No man of recent acquaintance (or non-recent, for that matter) who thought it appropriate to comment on my choice of attire would ever see me twice.

Have to say your grandad has very old fashioned views for someone in his 60s!

I think the phrase is usually " a nicely turned ankle", referring to a tantalising glimpse of a Victorian ankle when owner was getting into a carriage, or over a stile, etc. I assumed it was a description of the shape, as in joinery when table legs are turned on a lathe. Pedants' Corner might have views, though.

I don't think it's about wearing a dress or skirt necessarily, as women can definitely look sexy and feminine in jeans.
I think you could flex your look a little for a date, but still be comfortable that it reflects your own style. I saw The Pretenders at Portsmouth Guildhall in the early 80's and Chrissie Hynde looked amazing in black leather jeans, (not too high) heeled boots and a white frilled shirt under a pale grey cropped military jacket and from what you've posted about what you like, I don't think this look would be too alien to you. You could swap in your biker jacket and achieve that "tough/luxe" (or cool/sexy) look easily.
Personally, I think it's most important to dress appropriately for the occasion/venue so I would also have worn jeans to Bills too, but paired with heels and a feminine top (it's definitely not a "sexy" dress kind of place!

The op wasn't after styling tips though.
She sounds perfect fine as she is without trying to look cool or sexy.
If that's how Op feels comfortable and the blokes don't like it it really isn't the OP'S issue. Better to weed them out rather than have them controlling what you wear once in a relationship.

Sorry, I can't agree with you at all that it's an age/generation thing - maybe in your family, but not in my social group. Like @handsdownthebest "jeans and a nice top" (with heeled boots in the winter or heeled sandals in the summer) is my go-to for "smart casual" dining and I'm early 60's in age. Now, if I'm going to Lime Wood for lunch or dinner, that would be a different matter ...

Men are visual but some have a plank in their eye.

This made my skin prickle in anger on your behalf OP. And I'd have got up and walked out the second he started pulling faces. Your style sounds great. It's definitely a him problem.

That's the crux of it. It's the audacity and entitlement comment and criticise.
What they're saying is: I could find you attractive/sexy/ beautiful if...
They arent quality people and fortunately they are making it very easy for you to avoid them.
It's not you, it's them.

It's fucking rude for a new date to comment on your clothes.

It's - IME - unusual for women to wear skirts, especially in winter. My friends and I tend not to!!

It sounds like you are more alternative and the men you are dating are more conservative? Made you need to zuzz up your profile to make this clear!!

But Bill's?? I'd wear nice jeans and a good top too. It's not the Ritz!