Thought I'd resurrect this thread, since it's such a fun topic!
Personally, I have sported both ultra-short and ultra-long hair throughout my life, as well as the all-popular shoulder length. Long hair camouflages my super round cheeks (oh, to have high cheekbones!) and can be very versatile and feminine, but I also love the creativity and easy chic of of well-cut short hair, like the pixie a la Angie, Suz, and citygirldc, to name just a few on YLF! I agree with those saying all lengths can be stylish, depending on the health and cut of the hair. Of course, bad grooming, frazzled ends, no shape are not the most chic looks ever! Definitely the wisest advice is to have a hairstyle that suits your personality, lifestyle, face, and hair type! I guess that means I tend to be a bit...eclectic...lol.
Recently I had my very long hair cut into a nape-length angled bob with long bangs, which I quite love. Much easier, and it definitely feels a little more 'my age' (39). I'm experimenting with different "texturizing" products like pomade and hair mud, etc., to see what I can design.
One ironic - and strangely irking - thing I've noticed, though, is that quite a few celebrities who are considered "stylish" happen to have long, shaggy-like hair which I think makes them look less polished! I.E. Sarah Jessica Parker http://somecommentsonthetheatr.....ca-parker/, and Penelope Cruz
http://www.google.ca/imgres?q=.....#038;ty=69
(Sorry, no idea why those links are soooo long!)
Anyway, just piping in to say to each her own, I suppose! Perhaps to my eye these ladies' looks are a tad umkempt, but to the beauty biz they're just sexily 'tousled' as they like to say. But SJP even gets away with major roots showing! Ah well.