I like your numbered system and for that reason I'm going to just rank them. In order of priority first, 4, 2, 3, 5, 1.
As I've pointed out in another thread, I think I've finally satisfied my shoe craving for the winter (well, I'm still looking, but I bought a pair of boots so I'm not looking hard anymore). I also sorted my pants situation a month or so ago, for the most part. Taking a glance at my wardrobe, it still needs a lot of work. I thought I'd throw out a question to FB about what I should tackle first. I need, in no particular order:
1) A belt (semi-formal, and perhaps casual one as well, although I have one from Uniqlo which can last for another year or two)
2) Some new pullovers/sweaters
3) Some new casual shirts
4) A spring/fall jacket
5) A scarf or two
What would you guys look for first? Because the seasons are changing, I'm wondering if I can find a deal on a spring/fall jacket, whereas (2) and (5) are probably full price. I think that (1) and (3) are always full price, so I could also look for those, so maybe I need to focus on (1), (3), and (4).
I like your numbered system and for that reason I'm going to just rank them. In order of priority first, 4, 2, 3, 5, 1.
It depends how well kitted out for the winter you are. If it was me, I'd make sure I had enough warm things in my wardrobe to keep me going during the colder months and worry about the spring jacket and the belt later. It's better to get the basics sorted and then start accessorising than the other way around.
Probably 2, 5, 4, 1, 3.
A good quality jacket can be a staple in your wardrobe so if you can find one that works well with a range of outfits then it will be key in the coming months. Pullovers and sweats are going to come in handy with the turn of weather in the past few weeks so they would be next most important in my opinion then the shirts to give more options and a more smart look. Scarf, for the same reason as the sweaters, will probably see a lot of use soon so that's next which leaves the belt last. It's not that I don't think a belt is important, just that you have said you already have one which is adequate so expanding the rest of your wardrobe seems more important to me. Without having seen what you have at your disposal currently that's how I'd rank them. However if you already own alternatives to some of them then maybe focus less on those areas and spend your money elsewhere.
It looks like both you are thinking along the same lines. That probably makes sense. There'll be more selection of winter clothes right now, so I can find a little variety. Maybe I'll get lucky and find something on sale, too.