I started writing this as an email to a female friend, but thought I'd post it as it might be useful for others. I'm currently working on, or trying to find, 4 different 'classic' bikes for 4 different cycle chics - all of them being new to cycling. They are all only spending $150-250 dollars and wanting something simple and stylish for summer, and nothing that requires lycra. There is a lot of bikes on Trade Me so after countless lost hours searching Trade Me and many more rebuilding old bikes, here's my bias view on some good options. Suggestions & questions welcome.
Nana style. Best for Tamaki Drive.
Raleigh's rule here. 70's or 80's models best. Solid but not heavy as such, they generally feel fast and nimble to ride. These are built to last and with a good service will keep running for another 30 years. Anything older gets a bit hard to find parts for. Anything from the 90's will be likely be poorer quality aluminum frames. Hercules is another brand - just a Raleigh in disguise.
Other options include a japanese import from Mamachari. They look great and come fully serviced and ready to roll but are at the top end of this exercise at around $350-$500, and are also rare outside of Wellington where the importer/retailer is based.
I'm a fan of Peugeots - from the 80's would be my pick. French flair but not too pricey.
Be transported back to 1982 on a Healing ten-speed or Raleigh 20. Just be prepared to wonder how as a 13 year old you ever managed to cycle up a hill. They weigh a ton. I still feel guilty for selling a Healing Cruiser for $38 to a 20-something girl who must have weighed about the same as the bike. If you only every ride downhill then fill your boots. These also seem to rust more than others, or maybe because they are cheap they just get left out in the rain more often.
Best thing going for them is ubiquity and price. I don't bother with them much but that's just my middle-age bias. Kids born in the 80's seem big fans.
Nowtro (new but retro)
These are new bikes styled to look old. Unless your spending bigger money ($500+ for a second hand model typically) on a quality bike brand like a Charge (pictured), Specialised or Trek, they tend to be cheap and flimsy 'warehouse specials' which some bike shops may refuse to even service. If your spending under $250 go for a genuine classic.
A final note. Good condition bikes like any of the above the above are getting very hard to find on Trade Me. Allow $55 to $85 to have a bike shipped for outside Auckland. Other sources are The Second Hand Bike Shop, Adventure Cycles, garage sales, small town second hand stores and your Nana's garden shed.