This is a charade (word combination) with an anagram. A charade builds the answer by putting together multiple parts, and an anagram rearranges letters based on an indicator word.
Start with 'Director' - take just the first letter. Then 'redesigned' is your anagram indicator - rearrange the letters of 'SINGER'S'. Put these two parts together.
Answer: DRESSING | D (first letter of Director) + anagram of SINGER'S (indicated by 'redesigned') = D + RESSING = DRESSING (clothing)