to be irritated by this?

[highlyunreasonable]

I have a few nice dresses hanging up in one of my wardrobes. Whenever I open this wardrobe and DP is around he makes comments about how he'd love me to wear one/ he thinks I'd look great in them/ 'why don't you ever wear them with me?' type thing.
My answer is always along the lines of 'well, take me somewhere I can get dressed up and I will' ...yet it never happens.
I plan stuff for us to do regularly - concerts, comedy gigs, days out with kids, things with mutual friends etc. If I ever suggest going out on the town/ to a nice restaurant he's never up for it, prefers quiet and local which is fine but not somewhere I'd wear a dress.
We're not rolling in money but we can afford the odd thing here and there, but since our first date about 3 and a half years ago (which was a lovely restaurant in town followed by a few bars that he planned all by himself) I don't think he's actually made plans without me telling him to. He's happy with a Nandos or a Wetherspoons so the extent of his spontaneity tends to be 'let's go for a Nandos!' (don't get me wrong, I love a Nandos but I'm hardly going to put on a frock and heels for half a chicken am I?!)
He made the comment again this morning about the dresses and it's starting to pee me off if I'm honest. Does he want me to do the fucking washing up in one?!

Hardly a issue really!

Surely there must be a quiet, local restaurant that isn't a Nando's? If you're setting the bar at Michelin stars, you'll never get any wear out of your dresses!

put them somewhere he can't see them?
Tell him to bugger off?
Tell him - in clear words - that you will wear it when he books a table at x restaurant?
Tell him - in clear words - to book x restaurant on x date? and then wear one of them?

You could draw up a visual aid to help him. On a sliding scale, Nando's, McD's,Wetherspoons: lucky if you put on a clean top. Pizza Express, Franco Manca, Bill's: not worth a dress. Côte, The Ivy: you might consider a dress but not tights. Proper restaurant: best bib and tucker and you'll run to full make-up.

Unless it's an actual ballgown, you can wear "nice dresses" anywhere.

I hate this "keeping things for best" mentality, why? Life is too short, it's fine to wear a dress to Nandos. I hate Nandos but my kids love it for some unknown reason

Don't suggest, TELL him going to a nice restaurant would make you happy. Don't wait to wear "nice" clothes, what a waste.

If you're never going to wear them donate them to charity.

If you want to wear them arrange to go somewhere where you feel comfortable wearing them.

@Bananacloud thank you for your helpful comment 🙄
@katy1213 haha I like that idea!

For clarity, I do wear these dresses if I go out with my friends - we tend to head out to bars/ clubs etc and while yes, I could wear a dress to Nando's I think my point is more that I cba putting effort into getting dressed up if he cba putting any effort into planning anything for us to do together

If he says it again, just reply 'we are not having this discussion YET again' and say nothing else. Hopefully that will make him wrack his brains to wonder why on earth you reacted like that to a one-off innocuous comment or make him think 'hmm, I WILL take her to a nice restaurant'. If he's anything like my DH, it will definitely be the former 🙄.

How does he respond when you say "take me somewhere nice?"

Why can't you plan somewhere nice for you to go to together? Book a table at the restaurant you want etc? Is it always your dp that chooses where you go? Do you not get a choice? Myself and dh usually discuss which restaurant we are going to eat at before we go.

^^
I was going to suggest that you book it too!

@Bbq1 @Blacksackunderthetreesfreeze
I know, you're both right. I can book somewhere, perhaps I will.... I might even go on my own 😂
Do your DH's ever use initiative and take you out without prompting? I know my post focused on the dresses but I think the deeper problem is I get a bit fed up with being the only one to ever plan anything. If it were down to him we'd never do anything for birthdays/ anniversaries/ valentines or, in fact, ever.

My dh doesn't take me out spontaneously as we have family commitments most evenings, but I wouldn't like that really as I like to pre plan and know what I'm doing. We do chat about where we might go for a meal beforehand and chose somewhere together to celebrate our anniversary/valentine's day.For birthdays we each choose the restaurant we would like to go to. It's just a mutual thing really, we chat and plan things beforehand. Maybe your dh isn't much of an organiser or really just doesn't think of it, so take the initiative and book somewhere really nice for you both.