A well-cut white shirt, waisted or not waisted, depending on whether or not you can darry off mannish tailoring. (I can't!)
A belted trenchcoat, in camel, like Burberry, dogstooth check or tweed.
A black leather jacket in a vaguely biker style
A traditional cut Levi denim jacket - not stonewashed
I personally favour bootcut jeans because of my height and shape, but true classics would need to be straight-cut (not skinny) and ever so slightly low waisted and slouchy.
Flattish high-leg boots like riding boots
A simple well-cut LBD. Cannot lose EVER with one of those. The plainer the better. Accessorise to your heart's delight.
Chunky 'ethnic' statement jewellery in silver, wood, amber, etc.
Pearls.
A hacking jacket
Wide, white floaty palazzo pants for summer
The classic-shaped (Men in Black type) RayBans in black or tortoiseshell frame
A large soft slouchy brown/tan bag.