This is somehow starting to feel a bit more like a manga that dispenses advice on the do's and dont's of dating for inexperienced young men. But first things first, she could do well by telling him to start using contacts.
Maybe part of the reason he's having trouble using fashion to express himself is because he doesn't have much personality to express in the first place...
So why couldn't she reciprocate his feelings if she finds him so hot she goes red in the face and has to hide? Is she keeping a trauma hidden away somewhere in her heart? I hope that's not the case though.