I've always used boots, and Redwings for the last 25 years.
I would not use hiking boots unless they had good strong covering of the ankle knob. You need protection there in case you go sliding on asphalt. I don't think that part of the body grows back too well after being scraped off.
When I used to commute at 5AM, it was pretty cold, just above freezing some days. I bought a bomber jacket, fleece lined, with elastic sleeve and waist seals. The bates gauntlets fit right up to where the leather began on the sleeve. For the neck I used an acrylic scarf, as wool was just too itchy. Sometimes, I would also wear a sweater under the jacket. I found ski pant lowers at a sporting goods store. These had zippers up the sides and snap closures around the ankles and waist. They were thick and warm and excellent at blocking the wind and rain water. They went on and off very fast at work. I should have gotten them one size larger to prevent the air ingress in the back between waist and coat, though. These could easily be bungeed onto the bike when not need during the warm part of the day.
I finally got a First Gear Scout jacket that works much better than the Bomber jacket. It seals in all the right places, has an effective neck cover/ seal, extra long in the back, removeable thinsulate lining, and extra long sleeves, for when your arms are outstretched in front of you.
Nicest of all, I can still wear this coat in the summer, as it has zippered vents chest and back. Plus it has unzipable scoops near the sleeves to catch the breeze up your arms to vent out your back. If you are moving and there is a cooling air, you can wear this leather jacket in the summer,too. It's the best motorcycle jacket I've ever found. However, I do wish it had armor for the elbows and shoulders.
Cheers,
