OK this is gonna be a bit of a weird one.
My DP has had various insecurities about his looks for as long as I've known him. He has been very bothered about losing his hair for years, constantly goes round the house with caps and hoods on etc. and recently got a hairpiece, which he claims to love but he's constantly faffing with it. I don't mind all this as such but sometimes he'll wear all this to bed as well, claiming he's cold but I know he's doing it to hide his head. He'll wear it all when in public about 95% of the time, including at parties etc so people don't really see his face. We've been turned away from restaurants and bars before as he keeps his cap on. He's also slightly overweight, so wears a t-shirt even when we're intimate and has always preferred positions where I can't see him e.g. spooning or doggy. I really want a closer emotional connection while I'm physically intimate with him, but he has always been skittish about it. Recently he's also started going off prolonged kissing as well, which I miss, saying he's just not often in the mood for it.
How can I boost his confidence about his looks? I'm often saying to him how handsome he is, specific things every day about what looks or feels or smells good about him, which he seems to appreciate but he's still so critical about himself and still covers up. Occasionally he'll joke with me about his weight but the t-shirt will stay on during sex and something like a shower or bath together would be absolutely unheard of.
Alternatively should I back off completely and let him chill out about it all? I don't want to put more pressure on him about our intimacy, as he already has a lower libido than me and I wait for him to initiate every time, as the rest of our relationship is great, but I miss feeling as physically connected to him in bed.