There are the Sienna Millers - you know, the kind who can just throw on a Granny cardigan and suddenly that sparks a trend.
Then, there are the ones whose sartorial styles depend on the girth of their wallets. Walking testimonies? Most of the tai-tais you see at any chi-chi event.
So what distinguishes the ever-stylish Kate Mosses from the monied Katie Holmeses of the world?
Fashion stylist Trey Wong, 29, says having true style is not about following trends.
'A stylish person edits and reinterprets trends to fit her personal style. And she would be able to look good regardless of how cheap or expensive her outfit is.
'You also need the natural confidence to pull off what you wear. It could be a Prada dress but if you can't carry it, it's pointless,' he says.
It doesn't matter how fat your wallet is, how old you are or whether you channel Parisian chic, the post-modern forms of Japanese designers like Yohji Yahmamoto and Rae Kawakubo, or just plain high street.
The beauty of fashion is that it is diverse and allows a person - of whatever age - to arrive at their own personal style.
Some of these journeys are long, some are short, but as the following eight stylish women show, you can't be at the top of your game without making a few mistakes along the way.
After all, a stylish woman knows: You wear the clothes. The clothes don't wear you.
Additional reporting by Trisha Suresh and Wong Pei Yee