Yea, in cooler weather success is all about picking the right layers… especially when windy.
When running I want to be warm enough (or maybe a bit cool) in beginning and cool enough (or maybe a bit warm) at the end. Of course on the trail the layers need to be portable.
One trick I have for having extra pockets (to stash shed gloves, hats, headband etc) is to add an extra pair of shorts over leggings. A pair of hiking shorts abandoned by grown son has been especially helpful on the coldest days since windproof with many pockets. I have not donned them this winter though since a lot of the cold weather has had too much wind and/or ice on trail. Also I’ve gotten wimpy, more willing to do indoor training bike instead (while watching Grey’s Anatomy on Netflix, now up to Season 16 )