You can subclass Date with your own printing method, but it's probably not worth it.
If you use chron, you can associate a format with each object:
library(chron)
c1 <- chron(c("02/27/92", "02/27/92", "01/14/92")); c1
## [1] 02/27/92 02/27/92 01/14/92
c2 <- chron(c("02/27/92", "02/27/92", "01/14/92"), out.format = "y-mmm-d"); c2
## [1] 1992-Feb-27 1992-Feb-27 1992-Jan-14
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