You will need to go for a large in the pro team softshell and medium in the classic I think. They are quite different jackets so it would be worth seeing them to make a reasoned decision. I love the PT softshell although it would not work so well for slow-pace winter miles. It is designed for tempo bad weather riding, which it excels at. The classic will allow more freedom for layering as it is a more relaxed fit. The PT is very close fitting, which it is supposed to be. I normally wear a medium in Pro Team but I went for a large in the jacket as I found the medium to restrictive.
You will need to go for a large in the pro team softshell and medium in the classic I think. They are quite different jackets so it would be worth seeing them to make a reasoned decision. I love the PT softshell although it would not work so well for slow-pace winter miles. It is designed for tempo bad weather riding, which it excels at. The classic will allow more freedom for layering as it is a more relaxed fit. The PT is very close fitting, which it is supposed to be. I normally wear a medium in Pro Team but I went for a large in the jacket as I found the medium to restrictive.