I'm over 40 now, and I'm starting to get concerned about dressing too young. I have a cool vintage print dress (hits just above the knee) that I want to wear with plain black leggings. Can I still get away with this?
Wow, I hope it is sill OK! I am over 40, and wear skirts / dresses with leggings what feels like every day!
Truth is - it depends on YOU and your style. I know a lot of stylists out there (who I greatly admire) who strongly disagree with me. In my opinion, your personal style comes from within more than it is about what is hanging on your shoulders - or on your legs (for that matter). If you wear that great vintage dress and throw on the leggings and feel great about it - GO FOR IT! However, if you put on that outfit and feel self conscious and a wee-bit uncomfortable, then that particular style isn't for you...might want to skip it.
Also consider your shape. Some women simply don't look good in the legging / dress (tunic) look - regardless of what age they are. Be very aware of WHERE the legging is hitting your leg, because that is where people are going to look. In other words, if you don't want people looking at your gams, this might not be the best look for you.
To prove I wear this look - here are some pics of me, this past week, wearing leggings in (what I think is) a grown up way: