Athletic headbands (labeled with soccer balls, ADIDAS, etc.) or Pre-wrap should only be worn by athletes immediately before, during or after an athletic event. If you played JV Volleyball it's time to lose that stretched out circle of sadness.
Hippie wraps or turban headbands. I only like to see these at the pool, on vacation, an event like a concert, or any outside activity. In the appropriate venue these look chic and effortless.
The classic headband. Tease your hair at the crown a little to keep it from looking flat. Sweep it up into an updo for a romantic look.Throw some hot rollers in your hair for big volume and slide in a shiny headband for some serious polish. I love it.
Headbands with giant flowers, poofs, feathers, etc. Also, for some unknowable reason, the girls who wear these wear them with completely straight, flat hair in a pony. Really? You're going to make the focal point of your look the giant accessory atop your head? You look like a Teletubbies character.
Bandanas. I'm never going to say these are ok. If you don't work on a construction site, lose the bandana. Simple as that.
Headbands that are braided synthetic hair meant to look like it's yours. Claire's called. They're apologizing for selling you something that is so clearly a 90's joke. Do this instead. Way cuter and easy.
The zig-zag headbands that dominated 2000-2004. I thought these were extinct but then I saw this ancient artifact on a lady at Walmart.