This is how the Chip and Dale costumes changed in the parks.

Image Year Description
Ice capades 02
1950s The original Chip and Dale costumes, like the majority of early Disney characters costumes, originated with the Disney sections of the Ice Capades shows of the early 1950s. They were borrowed by Disney for the opening of Disneyland in 1955. Chip's eyes faced forward while Dale's eyes were crossed. They had ringed collars on the heads.
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1960-1968 In the 1960s, they looked identical, with no character distinctions between them.
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1968-1980 The 1970s Chip and Dale costumes introduced unique head shapes to give individual personalities and looks to make them easier to tell apart. They are more cartoon-like in appearance than any other version up to this point. Dale was given different designs to differentiate from Chip including thicker eyelids, a rounder and more brown nose and two separate teeth on both sides of his mouth.
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1981-present The current Chip and Dale costumes, seen since the early 1980s, have gotten new, smaller heads with bulging cheeks, and the extra neck fabric was removed. They've also been given distinct characteristics. Their hands are now four-fingered.
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2008 -present The articulated versions of Chip and Dale, seen in various live shows. Notice that Dale has a hairpiece on the top just like his animated version. They also are slightly shaggier.