Combining two of a woman’s best friends – diamonds and shoes, the Diamond Dream stiletto pair is an expensive shoes priced at a half a million dollars ($500,000). Unbelievable as it may sound, this is actually considered as Weitzman’s least expensive pair in his Oscars collection. This pair was created for the 2007 Oscars and was worn by actress Anika Noni Rose. It is studded with 1,420 diamonds and was inspired by the circles collection from the leading jewelry store, Kwiat. The Diamond Dream is all glamour with the bands of diamond-encrusted circles.