He will dress quite trendy, but understated. Smart/casual. This could be simply some nice jeans, a graphic t-shirt and lace-up boots.
Current girlfriend
She will be dressed in designer clothes, with quite a loud image. Very fashion conscious. Perhaps a leather skirt with a graphic blouse and heels.
Ex girlfriend
She will wear quite understated clothes, will look good without trying too hard. More natural colours; tries not to stand out too much. Dark jeans and a nice patterned top with flats.
Dad
Very basic clothing. Not much thought into what he wears. Jeans and a plain top.
Mum
Quite stylish but again, very understated. Possibly some knitwear, mum jeans and walking boots.
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