Headbands: Is there an age limit? Fashion Police?

Is there an age limit on headbands?
I would love to wear a headband.
I would like to knit a headband.
When, and why, did I stop wearing headbands?
There seem to be a lot of them in the magazines, on TV, out and about. The patterns are everywhere, if a pattern is really needed to knit a headband. Headbands seem to come in every fiber, texture and color. Wide, skinny, slick, chunky........ The store's got a whole row of them in the haircare section, as well as endcaps full of them in each department for female clothes. They've even got them in the dog food aisle for the little doggy darling.
Are they really that popular in real life? A few weeks ago, in the coldest part of winter, I saw an older (than myself) woman wearing a scarf-like headband about 4 inches wide. It was beautiful. But, I couldn't help wondering if she was wearing it to cover up a hair issue: hair loss, needing a dye touch-up, covering the wig line, who knows?
One of my lifelong issues with headbands has been the slide off factor. I don't seem to have enough hair, or maybe the right texture hair for a headband to stay on my head. It has to be pretty elastic, and not too slick, or it'll just slide right off. Maybe it's the shape of my head. Or the size.
Pet peeve alert: Not everyone is the same. Imagine that. Anything that is "one size fits all" will probably not fit most people very well.
And why is it that a headband that is tight enough to stay put will invariably cause a headache? You know; much like that headache from the brand new glasses that squeeze your head 'till the dents behind your ears are permanent. I have always suspected that the reason the glasses stop hurting after a while is because they've killed the nerves. But, I have always had problems with the dime-store plastic headbands because they really hurt to wear.

Then there's the fashion issues. Is it really fashionable? Am I too old for this? Does this headband make my butt look big? Does it make my head look funny?
I have to admit that although I love to knit hats, I have yet to knit one that I like how it looks on me. That hasn't always stopped me from wearing them. Even when my family says "Ohhh, maybe you ought to check the mirror". If Gilda Radner could admit to basing her fashion sense on what doesn't itch, I can base mine on keeping warm and/or cool. And now, my kids tell me that hats aren't allowed a lot of places they go because of "security issues" and "gang overtones". What is that about? And, at where is the line where a headband becomes a hat?

I went through a (non)fashion phase a few years ago where I didn't cut my hair for a long time and wore a headband almost every day. The Goody company made one that I loved, for about 2 years. Now I can't find them anymore. The ones that I had have all broken - the risk of wearing cheap plastic. And - my DD1 got a hairdresser friend to threaten me, cut my hair, and make me swear to quit wearing any "device" on my head that cost less than 99 cents each. They were trying to tell me it wasn't good for my "professional image".
So, what's the Fashion Police say? Can a professional grown up woman wear a headband? And what would it look like if she could? Could it be a hand knit? Well coordinated with the outfit?
Keep in mind that my idea of "doing my hair" is limited to dandruff shampoo no more than 5 times a week. My "hair tools" are limited to A Comb and A Hairbrush. Sometimes, I actually look in a mirror while brushing through the wet hair. While I do own a curling iron and a blow dryer, both have been used by DD2 on her puppy more this winter than ever on my hair. Not counting the shower time, the average daily time spent on my hair probably averages out to less than 3 minutes per day (but only if you add in the time I spend with my "Colorist" (DD2). She likes to "paint in the blank spots where all the color's missing" for me. That's about as good as I can do for girl's night.
So, what's the Fashion Jury verdict? Skinny or Wide? Over the ears, or behind the ears?