I think this would be a bit daunting for a lot of people, and would lead to a lot of "what if" questions which would slow you down, So instead I would advocate packing away all your summer clothes first (or vice versa if you are not dong this in winter) not only will this mean that you have a smaller job to deal with, but also you won't be flooding charity shops with out of season clothes that they will have to store until the market for it is there.
When I did my cull, I packed away all my ski stuff, my office stuff and my summer stuff because I wasn't using them at the time, and then after the first clear-out it was easier to deal with the other sections.