Packing question: dressing for dinner in upscale hotel

[RingofBrodgar]

DH and I are going to a lovely 5 star Italian hotel to celebrate a big anniversary. In the past , I’ve always had a different outfit for dinner every evening. This year I only have 3 dresses which make me feel great. So my favourite dress would be worn 3 times across the week and the others twice.

I am interested in how others pack for a similar sort of break. Do you repeat favourite outfits or do you have something different for every evening?

An Italian hotel full of Italians? Or a US brand hotel? That will make a big difference on how dressy evenings are, Italians will often dress up for dinner, which wouldn't start before 9. Having dinner in the hotel at 7pm, is a far less dressy affair.
Also remember it will be hot even outdoors at 11pm, so choose your materials wisely. You can totally rewear a dress, especially if you are only in it for dinner.

I’d be unlikely to wear the same dress twice in a week but I did wear the same skirt twice in the week on a recent holiday, with a different coloured top each time, and I’d be likely to do that again to save space. I also had one shirt and shirt set for two beach days and one set for two pool days as I knew I wouldn’t be wearing either for long. I would probably be more likely to wear the same dress over a two week holiday and would definitely be getting a couple of uses out of at least one skirt and pair of trousers across that time too.

That’s just personal though and I wouldn’t see anything wrong with wearing the same dress two or three times if that’s what your comfortable in - comfort is key and most people wouldn’t even notice!

I always pack one outfit per day, and often wear a fresh outfit one evening and then rewear it in the day a few days later, possibly at a different location.

Thanks for the responses - some good suggestions and interesting to hear what others do 😊
Normally we would go out to neighbourhood restaurants but we deliberately went half board here as this place is relatively isolated and has lots of awards for the food. There are usually a lot of Italians in the hotel apparently and we will be eating fairly late.
As suggested I probably will take some separates too for evening so that I’m not wearing my favourite dress 3 times. However, I will repeat some nights.
Good reminder about messy Italian food 😊 I am the world’s biggest slitter (favourite Scottish word of all time) so will need to build in some contingency.

Surely that’s what napkins at the table are for?