I suggest a nice blouse and long flare leg dress pants that reach the floor and definitely some nice open toed high heels with a cute pedicure. Nice makeup and polished nails or have acrylic nails put on for the occasion. :-)
Well it depends where she's having it: Restaurant- Dress and heels/flats. House/Park- Crop top and high waist shorts with a knit cardigan with some converse or vans. Beach- Shorts and Crop top and flats.
Maybe a party dress with heels? Or jeans and a dressy top?
Wear this, will let him shine at the moment