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!

Hasn't happened to me but then I wasn't OLD that long.
They sound awful, and rude.
I guess at least they are showing you what they're like early on!
Do you need to improve your early filtering chat to weed out these types earlier on?

Honestly I think it’s an age/generational thing.

I’m in my 20’s and although I do sometimes wear a dress for date nights etc with my husband I also wear “jeans & a nice top” type outfits. He’d never say anything about me being not dressed up enough & loves the outfits (although full disclosure maybe he has a very low bar at the minute because he’s used to seeing me in PJ’s/leggings and covered in food/sick/dribble stains from looking after our baby all day🤣).

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!

I have no idea what's going on OP as I've never experienced that. Jeans and a top seems very suitable for a burger place. Are they showing up in a tux?

You're obviously choosing the same type of man if they're coming out with similar comments. Perhaps it's time to shake things up.

I have wondered about how to filter them out. My profile has me in casual clothes, not one dress or skirt so they know what they're getting. I'm boyfriend blazers and jeans in profile pic! As for them, I don't know how to filter them out. None of them have been conservative with their dress in their profile pics...

I’ve had the same but been told I’m overdressed - for wearing a midi or maxi dress and trainers which is my standard attire.

Usually by blokes who turn up for a date looking like they’ve slept in a skip or on one occasion wearing a football shirt, shorts and flip flops

Though-to the opposite extreme I once went on a Saturday afternoon date to a cafe/bar and he turned up wearing a suit and tie complete with pocket handkerchief which I felt was just a bit OTT

They want to see your ankles!

Bums and boobs are the obvious things look at in a woman but a nice turn of an ankle and great legs is also something most men are interested in looks wise and that's why they like to see women wearing dresses on a date.

God forbid he later discovers that you have cankles if you always cover your legs with jeans and trousers!

It's happened three times, twice on early dates, and one comment from someone I saw for two months who said "Why do you never wear a skirt?" They are showing up in smart shirts and trousers, where as I'd rather date a man in good jeans and trainers, a bit like me, but even if they have that on some pics, it's still happened three times too many!

I’m also surprised at that op. I am your age and done lots of dating and never experienced that. Some older people are a bit funny about trainers but you say you were in boots on your last date and the bloke still commented. Very weird. I agree it could be the ‘type’ you are going out with. Are they traditional/old-fashioned/snobby/a bit up themselves? What type of jobs and backgrounds do they have?

I have good legs, but rude buggers won't get to find out! Also, this theory that women have to show the wares before getting in the sack is a bit old fashioned surely? This notion that men are visual creatures is surely just a device for the patriarchy; women are visual too, but we are not asking men to show up in in form fitting clothes so we can check out their bits and pieces (oh, that is an awful image, erase that.)

Like I said it's never happened to me. Are you dating 80 year olds who want to go to a tea dance?

I'm your age and when I was doing OLD never once received negative comments on my clothes. I wear jeans, trainers, tops, boots etc I go to pubs or cafes on dates; never received a comment.

Good point about them wanting to see your legs. I arranged a date with someone I was chatting to online who seemed really nice but he started going on and on about me wearing ‘sexy high heels.’ He put so much pressure on I cancelled.

He sounds like a prat. He expected you to dress up for Bill’s?! Bill’s?! Maybe he doesn’t get out much. 😜

The outfits you’ve described sound fine to me. Stylish even. 👍 And I’m 54 so I don’t think it’s a generational thing.

It’s also incredibly rude of him to make the comments he did. Arsehole. When I was last dating, my date didn’t comment when I turned up wearing my still
sweaty gym kit (with a sweatshirt over the top) even though I was slightly embarrassed when I saw he’d put his “Sunday best” on. Oops! 😂 The next time I actually showered and put some make-up and clean clothes on just to prove I wasn’t a completely heathen. We dated for quite some time (and we’re still friends) and he describes my dress style as “flamboyant” 🤣 but not once has he ever been less than complimentary. Throw this one back. You can do better.

I'm the same age as you op and I'd never wear a dress on a date.

Your outfit sounds great (especially the wedding one). Throw this one back. I think men get to a certain age and suddenly turn into their fathers and expect women to have long hair, wear dresses and high heels. All a bit misogynistic to me.

They've been a mixed bag, really. All with reasonably good jobs, and no tuxedos or three piece suits on their profiles. I'm obviously attracting a certain type though...

Urgggghhhh just as rude, especially from the skip men!

Tbh OP it doesn’t matter what you wear, it seems that middle aged men on dating seem to think they’re entitled to comment upon your appearance despite most of them having the sartorial elegance of Worzel Gummidge.

All of my friends who have done OLD have said men comment on their clothes, hair, car they drive etc. Rude and entitled

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

You're not out of touch, they sound like hideous men who want their women trussed up in bodycon dresses with heels like a throwback to the 80's when they were teenagers wanking over mags. Yuckity yuk.

Fwiw OP I think the way you describe your dressing style it sounds brilliant.
I think it shows you are an individual with personality.
I don't think it's a " you " problem. It's very much a problem of society these days wanting women to be like sheep and all look the same.And the guys you are meeting buy into the expectations heaped on women. They sound extremely boring and tedious.

It's just really bad manners. Also, I've never had a comment like that from a man who could put a decent outfit together himself, not that I'd like to be insulted by anyone, but you know...

My previous post was from how I think a man would think not my opinion!

I think what you wore was fine for a first meeting in a casual place.

If you go in head first all dressed up to the nines what has he got to look forward to?

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.

It’s this. I’m decades married so not OLD but have friends who are. A lot of the men seem to want exactly that - lots of makeup, obvious blow-dry, bodycon dress and heels, clouds of perfume, professional nails.

He probably wanted you to wear a skirt or dress so he could put his hand up it...

What was he wearing to eat at a burger bar? His clown suit?

You’d look so weird all dressed up to go to Bills 😂😂 did he think it was a fancy place?