Boots: Motocross/motorcycle boots have the best protection, but are often times so stiff as to be all but impossible to walk in. Make sure you actually can. Tread design matters, so your foot doesn't slide on the ground. Oddly (imo), many motorcross boots have effectively no tread. Good high top generic boots also work well. Beware the ability to get them off when hurt. Laces are nice then, trying to pull a cowboy boot off a broken foot hurts real bad.
Gloves: I struggle with these, as many motorcycle gloves cause me problems or don't actually protect very well. Slippery suede like palms that slip on the handlebar grips. Lack of feel so I death grip the handlebars, exhausting my forearms and numbing my fingers. Thin palms that make me question how effective they would be sliding down the road. Stitching and seams are often poorly places for maximum discomfort. Generally, if I'm going to be wearing gloves, it's most likely to be a set of generic leather work gloves.
Heat: I've had heated gloves, they were completely ineffective. These were the battery type, not the plug in type. I've heated grips on the snowmobile, and while I like them, toasty they ain't, and the cold wind on the back of my hand and fingers is just as cold and numbing as it ever was, even with a sweaty palm. Goofy looking hippohands or similar have worked the best for me for winter riding.
Pants: I've been wearing leather chaps for many years myself. Leather provides great abrasion protection and great wind protection. I like them. I do have some textile over pants that are armored and mesh for summer riding. Not bad, but not great either. Yes, the mesh lets me wear shorts under them and strip them off when I get to where I'm going. But the textile means I can't actually grip the tank, and the armored knees slide around and make it hard for me to feel the tank. I also doubt the knee pads will be in position should I hit the ground. The butt padding and protection raises me up a little and further reduces feel, which makes it harder for me to comfortably control the bike. But, I'm practicing wearing them and trying to like them. It's the Detour house brand from Jafrum.
Heat II: I've an old school Widder electric vest that has worked well for the many years I've had it. No, it isn't absolutely cold proof, but it sure helps, when I've got a wind proof outer layer and enough insulating layers over it. There are some new and very interesting infra-red heating systems. They include a full sleeve jacket liners, pants, socks and gloves. If I were doing more winter riding, I'd be awful inclined to try them.