Remus it depends which Greek Island you are going to. Busier islands with more organised tourist resorts such as Lefkas and Skiathos require a different wardrobe to less organised places such as Naxos. In the former you may well feel that you want to get changed for dinner - albeit in a casual, light summer dress kind of way - whereas in Naxos we literally strolled off the beach at 7pm into a taverna!
IME, it is too hot in August for trousers in Greece - whether they are crops, linen or whatever. I do, however, always take a couple of large cotton scarves/wraps with me. They are brilliant on the plane, covering up shoulders where appropriate or protecting your skin from the sun, wrapping up little ones who want a nap etc.
My 2 week holiday wardrobe usually consists of:
2 x maxi dresses (1 cotton, 1 jersey)
3 x strappy dresses (2 cotton, 1 jersey)
1 x 1-shoulder dress (not sure of technical term!)
kaftan-style dress, just above knee length
2 x leather flat sandals (1 silver, 1 gold)
Day wear:
bikinis (usually 3 or 4)
long loose-cut vest tops (Tesco, Primark & H&M)
2 x shorts (as in short-shorts, not bermudas )- try TK Maxx for Hilfiger & Roxy which are really flattering but be prepared to size up
2 beach dresses
flip flops
It seems like quite a lot written down but I find that a combination of insect repellant and sun lotion makes some things unwearable after 1 or 2 wears.