Google "Jon Renau softies" or other light bamboo beanies. These are great for lounging at home in, for wearing under scarves and even for sleeping in (keeps your head warm). I found earthy colours like brown, black, grey and dark blue looked the nicest:
2. Beanies with hair for winter
If it's winter, no one will blink when you walk around in a woollen beanie. It'll keep your head warm too! Surf shops are a great place for beanies, and Etsy has some nice ones too.
3. Scarves / headwraps - for evenings and the office
Scarves are a great option for work and evenings, and no need to master scarf wrapping techniques - just tie it on top of a soft bamboo beanie.
Vintage kantha fabric wraps made by BrooklynRose on Etsy - tied over a bamboo beanie these and other scarves are a stunning option.
Jon Renau softie wraps are a great option too - so easy to put on. Perfect for going out at night and perfect for the office.
House of Christine also has an amazing line of Turbans that I'm sure would make for an AMAZING look for an office or out on the town.
4. Sun hats with hair
Look for wide brimmed sunhat that have depth to cover the headband. Helen Kaminski make beautiful sunhat that often have the depth you want.
5. Caps with hair (without a hole at the back)
When looking for a cap choose one that doesn't have a hole at the back (usually where a ponytail goes through). I found one without the gap in a surf shop.
6. Newsboy and baker boy hats with hair
My favourite hat during chemo was a "newsboy hat" I'd picked up in Chile a decade ago.
Etsy and other online shops have a great range of beanies, scarves and hats with a hippy vibe - search "slouchy newsboy hats", "baker boy hats" ,"slouchy beanies", "summer beanie", "slouchy hat", "boho head wraps" are some useful search terms.