Not a whole lot of advice here, other than some commiseration. My ds is 15 and still hates socks, shoes, jackets, etc. After a certain point, I just started to let go a bit and let him go without, hoping he'd figure out for himself that he needs to wear certain items when it's cold out (or a hat when it's hot.) We live on the Canadian Prairies, and he still hasn't gotten frostbite or injured in any way, so I've just accepted that he knows his body better than I do and is smart enough not to freeze a part or two off
He will put on proper clothes when it's really, really cold, so I guess he just needs the right motivation.
I second (or third, etc) the suggestion of tighter clothes, seamless clothes, etc. Ds actually had a pair of the Padraig slippers for one winter. I also always picked out clothes that were a little harder for him to put on himself, meaning it was also harder for him to take off by himself (pullover anoraks instead of jackets or parkas, lace up boots, etc), so that he wouldn't go half naked at recess on -40 days.
No advice on actually getting your child into
the clothes though, I never really had to wrestle ds, he would just go limp, it was more like stuffing sausage