My DH 'does' smart very very well, but casual- not so well. I'm talking navy blue cords, random old t shirts, woolen jumpers, and rugby style shirts, with a smattering of more expensive outdoorsy stuff (icebreaker etc). He acquired his first and only pair of jeans a couple of years ago (armani), but they were a freebie and he would never have bought them. He makes some, token, effort not to dress like his dad, but not much. He doesn't like to be scruffy, but likes to be comfortable, and really doesn't see the point of spending much money on clothes that aren't practical (e.g. he has ten year old trousers but a £250 anorak, sorry, waterproof). He is medium build, 5'10ish. He wears smart trousers and shirts for work, and looks great (IMO!).
Don't get me wrong, I love him to bits and am no fashion goddess myself, but I am aware of what suits me and of dressing my age.
So... he needs some new trousers, and his birthday is coming up. He turns his nose up at 'trendy' things in topman/next as 'unnecessary' or 'impractical', and at 27 I don't think he is ready to be a grandad...
Surely it shouldn't be that hard, but where the hell do I start!?