What's the dressing up culture where you live? (I.e Liverpool & Essex are well known for glam, Newcastle is a complete mix, I hear London is fairly casual in style now.
I live in a small, upmarket market town. A fitted dress would be completely over the top.
I went out last weekend, cocktail bars and late night dancing, and wore flat sandals, and a slightly cropped vest with the below skirt. The skirt got lots of compliments.
https://www2.hm.com/en_gb/productpage.1166804004.html
Another in our croup wore smark khaki trousers with a pleated front, and a white halterneck top, with flat sandals. Another wore a floral midi dress, I think with small heels, and one wore a satin midi skirt.
My 19 year old is a regular clubber, and normally wears parachute pants with a fitted top and trainers.
What I took from the night out, is that for that for the first time in my life, when people say anything goes, it's genuinely true! Normally I take that with a pinch of salt, but the range of outfits from smart to casual was very broad.
So, that being said, what do you feel comfy but still dressed up in? If you want to wear flats, will a shorter dress make you feel a bit more dressed up?