Girl group first succeeded with brightly-coloured headgear (9)

I believe the answer is:

bandannas

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'brightly-coloured headgear' is the definition.
I can't judge whether this definition defines the answer.

'girl group first succeeded' is the wordplay.
'girl' becomes 'anna' ().
'group' becomes 'band' (band can mean a group of people).
'first' means one lot of letters go next to another.
'succeeded' becomes 's' (genealogical abbreviation).
'anna' after 'band' is 'bandanna'.
'bandanna'+'s'='BANDANNAS'

'with' acts as a link.

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