Leave out. Depending on breed/weather rug accordingly. Feed balancer for minerals and top up with hay when no forage and temperature drops. Beware September/October flush, then grass value will drop dramaticaly over winter. Listen to, and watch your horse, they will tell you...
My good doer is out 24/7 - muzzled in the day, when the sugar levels are higher - and off at night. Just a handful of feed for supplements. We are playing it by ear at the moment, as it's the first time since I've owned him I've been able to have him out 24/7 and if I need to, I'll bring him off the grass and feed soaked (and thoroughly rinsed) hay to avoid.
Leave out, don’t rug unless shivering. Will still need some hay though unless lots of grass. Should drop off nicely over the winter if aiming to lose weight.