this time of year i wouldnt worry about breaking them in, just wear them for riding normally and they will soon suffer plenty of soaking/drying cycles! but keep them clean of road salt/grit, it soon chews through boot stitching.
just give them plenty of dubbin/renapur/nikwax/balm/WHY, it really does make a difference over time, also, if you have any little bits of stitching sticking out get a lighter and melt them in, on gloves too. it really helps prevent the stitching from fraying over the years.
ive had the same boots and gloves for 7 years (boots HG tuareg gore, gloves some cheap tingtong rubbish from a bike show bargain bin, but they fit like, er....gloves) and they are still going strong, only just about feel lived in now