Like Tanya and Maya, I like to keep scanning for items throughout the season, really enjoy shopping, and would be bored by planning ahead too much. That said, with my wardrobe complete, it's fun to raise the bar and ask myself before each purchase, how much I need vs want something, do I like it or really love it (like Shell). And, is an item duplicating the purpose of something I already own.

One thing I've found is that I need more footwear than I ever would have imagined. Yes I own chestnut boots, but there are times when I need heeled chestnut boots to complete an outfit and only have flat. Apparently it's true that you can never have enough shoes!

I think for some years I did this. In 1999 I returned from overseas to my first corporate job and spent quite a bit (for me) setting up a work wardrobe. For the next 5 years I just bought a few things each year.
So I agree that this would be doable (especially if it was for the year, not each month) if your circumstances didn't change, size didn't change and your wardrobe was in good shape to start off with.

As I wrote recently I have set myself a shopping budget for the year that is pretty strict and may not get more than 12 items, fantastic or not. I tried to make a list for the coming year and have
Summer
- dress
-skirt
-graphic tee
-a ruffle tee with ruffles right down to the bottom hem
-elasticized ballet flats ( I havn't tried these yet)

Winter
-wool coat
-jacket of some sort
-a jumper (sweater)
-heels for wearing with dresses
-oxfords or similar

That is only 10 things so a bit of leeway there for new things to occur to me in the year

I've been using the 1-2 items a month/"plan" way to shop for a little more than a year now and it definitely has changed my closet for the better...though as an impulsive person in general, there's a large part of me that hates the bloodless nature of it!

[And try using this system when every other YLF thread is about the NAS and you've got no money saved up from past months and can't justify "borrowing" from future months, sob/ha!]

Given that I am not a highly organized person by nature, I find it a challenge to keep up with the seasonal closet analysis etc. that this type of shopping seems to demand (from me, anyway).

On the mega-plus side, the system helps me make the most of my clothing budget in two ways: by getting things that work hard for my money; by putting an end to closet orphans. It helps that my style skews more classic, so I don't feel pressure to wear the latest trends.

On the downside, it sucks when I go over one month due to needing basics (March's spring/summer shopping) or even worse, BRAS...the next month of deprivation feels reallllly long, ha.

I definitely have to do what Rosie said to keep from feeling too constrained:

>Within the plan you'd definitely have to build in some fun, inexpensive items, I think.

...usually on costume jewelry!

Mellls/Polly - I do hope I get it all, plus some additional extras! I work too close to the main shopping streets in London to restrain myself! But what I listed are what I feel are the essentials that I need for winter and I will probably add one or two new tops to the list in the sales.

I think that prior to finding YLF I didn't have a completely hopeless wardrobe. What YLF is helping me with is refining my style and finding pieces that suit my body type better.

Mellls - resoling shoes is definitely worthwhile, especially if the are comfortable and the leather uppers are still good. There are some shoe makers in London that will guarantee that your shoes will last a life time and in order to do this resole and heel for free.