Elizabeth of The Fabulous Dr. E's Fabulous Blog has an approach to sewing 6 garments every 3 months which would gradually build up into a self sewn wardrobe. She lives in a seasonal location (now Sweden, previously London) and back in 2009 suggested these guidelines.
I am a big fan, and although I have done multiple SWAPs and other wardrobe type sewing I have found this approach the most managable as you end up with stuff that's seasonally appropriate, goes together and achievable if you don't overcomplicate things.
Trousers (dark neutral)
2 Tops (1 to match, 1 to complement)
2 layering tops/cardigans/jackets (1 to match, 1 to complement)
Coat (dark netural)
I generally sew 6 things in the same colour scheme, not necessarily following Elizabeth's suggestions and haven't made a coat before even though I have done multiple winters, so I thought I should change that this winter.
So my plans for winter are:-
Trousers (dark neutral) - dark teal
2 Tops (1 to match, 1 to complement) - one teal, one an accent, possibly my pink
2 layering tops/cardigans/jackets (1 to match, 1 to complement) - one teal, one an accent, possibly my pink
Coat (dark netural) - teal wools
The tops would be simple knits, and the layers probably cardigans, or simple cardigan style jackets.
The trousers will be the current style I am fine tuning from a burda magazine and the coat will be made from several wool fabrics in my stash.
Here's what that might look like.
The tops will probably be my current favourite pattern which I traced off a favourite RTW sweater and modified a little. It has dropped shoulders and a loose boxy fit.
The cardigans will be a new style of my own making which I plan to draft to fit over the tops.
I'm hoping to come up with a 'one style works for many' that I can make up in lots of fabrics and sell on my charity craft stall. I'll write more about what I have planned on that another day.