I wear heels and leggings with sweater dresses (and other dresses). My key deciding factor is that the leggings must have a little "ruching" (sp??) around the ankle. A little "crinkling", if you will.
I find it gives a certain edginess/cool factor to the look rather than "look at these leggings which I have managed to squeeze my post-natal body in to and which are just about long enough"
My second option is leggings, sweater dress and ankle boots.
I too hadn't worn leggings since 86-ish (aside from brief grunge flirtation as <<ahem>> "mature" student in 90's). Can I recommend Top Shop extra long legging, please. Ultra soft (despite numerous washes), retains colour (I have navy and black), thick and flattering.
I bought the Top Shop extra long leggings recently and they are horrid. They bag horribly within seconds of being put on. Dd has found this too. She says they were never like this - she reckons they have changed recently. Her old pairs keep their shape but she hates her recently bought ones.
Oh no, Squishabelle - that is very bad news indeed about Top Shop leggings. I bought mine last December and they really are very good quality. They don't need replacing yet but shall not be hurrying to TS when they do, by your estimation.
Hey there - would totally second the American Apparel choice - am a huge fan of their clothes. The leggings are a little bit more expensive than other shops but do wash very wellno baggy knees etc and not shiny. They also have gorgeous high waisted ones as somebody else has mentioned.
They do have a website full of nubile young things !! - but work checking out for a look before you buy