I am a chypre lover too (I also tend toward orientals).
The Oriental and the Chypre families, by the way, have a lot in common:
a) They are the oldest in history (the first perfumes in antiquity were orientals, using resins, woods and spices - it wasn't until much later that we learned how to distill the essences from flowers; chypre bases - perhaps without the bergamot - were made in the isle of Cypress - from mixture of oakmoss, labdanum and spices)
b) Both chypres and orientals are based on a CONTRAST - in Chypre it is the contrast between the fresh-fruity notes of citrus (namely bergamot) with the earthy-mossy base of oakmoss, labdanum and patchouli.
Oriental perfumes are usually based on a similar contrast - citrus top notes and ambery base notes (for ambery orientals).
My favourite chypres:
Vol de Nuit (it has also some oriental or floriental elements)
Mitsouko (Fruity Woody Chypre)
Miss Dior (Green Chypre)
Femme (Fruity & Leathery Chypre)
Private Collection (Green Floral Chypre)
Ayalitta (Green chypre)
Megumi (Woody floral chypre)
Feuilles de Tabac (Leathery chypre)
There are many others that are beautiful, of course... But these are the ones I always want to have around.