Do reconsider bretons - they are so easy to wear. Plus you can get some much more contemorary ones now. I don't love the H&M ones, despite the press they get on here - too heavy, made me look slightly middle-aged (am 29 with 2 kids). I found one in linea weekend in HofF, which is significantly more expensive but much nicer IMO.
What you wear to go out all depends on where you're going out to. If you're doing Pizza Express with the girls a jazzed up version of your day clothes works, if it's a night out in a wine bar or in a swish restaurant you'll need to amp it up a bit.
For going out to a bar/pub, dark straight-leg jeans (well, ok, I'd wear skinnies but you've already discounted those!) with an embellished top and some kind of cardi over, and then accessorize it up. I know it's a bit boring, but there's a reason why lots of women go for this look - it works... Plus as you're petite, heels are a must for going out. Will lengthen your legs and balance you out.
For Pizza Express type meet-ups, flares (NOT bootcut) are really in this year, so there's loads around. To be teemed with wedges and some sort of blouse, I believe.
If I was going out with my DH on a lovely summer's evening date, I would wear a plain floaty dress, ballet flats and a little cardi if necessary.
HTH