How to decide what clothing to keep

I have lots of clothing. It is in several sizes, some of it is old, some handmade, some more recent. It covers various seasons. I keep on sewing because I enjoy it, but also I suspect because I've not quite got things where I want them yet.

I would like to have sort through of the wardrobe, and would like to develop some criteria for the process. I would also like to fill any gaps I have in the wardrobe for specific activities.

Here are some of the things I have thought of so far

- Does the garment fit, or if only slightly tight, may it fit shortly? (I am actively losing weight though slowly)
- Is the colour of the garment flattering to my personal colouring? (Or needs to be kept for another reason e.g. choir/work/sports team etc)
- If the item has a print or texture, is that flattering to my scale and consistent with my personality?
- If it does fit, is flattering and suits my aesthetic, what outfits can I make with it and where would I wear them? (If it doesn't have companion pieces then these might be wardrobe 'holes'.)
- Does it need special footwear, underwear or hosiery, and if so do I have it and would I wear it?
- Does it need special care and if so am I prepared to take the time to do that?
- Have I worn it recently or if not can I realistically imagine an event in the near future where I would wear it?
- Am I only keeping it because I need to have an X (insert garment here) for an activity but actually I am not happy with it when I have to wear it? (This needs flagging onto a list for replacement with something I would prefer.
- Is there a wardrobe 'hole' which needs filling, and if so what is it?
- Can I get dressed for all of the following - smart work meeting, normal work day, dress down work day, weekend, hiking, travel, sleep, gardening/DIY, party, trip to the pub etc?

Good post on this topic as always from Imogen from Inside Out Style Blog
6 Simple Rules for Cleaning Out Your Closet

And some more links to posts from Recovering Shopaholic
First Impression Test
The Keep or Purge Question
Paring down a large wardrobe
Closet Downsizing
Konmari in the Closet