I have now been taking (almost) daily photos for over a month and I have to say it has been one of the most helpful things I have done in terms of thinking about my style. I have had a few realisations from this exercise that I thought I would share with you.
1. I have enough clothes. Really. I have sufficient items to dress without repeats for about a fortnight, and that is plenty for me. Any new additions will need to be justified on the basis of love, rather than need.
2. Shoes make a huge difference. I bought 3 new pairs of shoes this season. I have worn them almost exclusively. It is possible that my shoes need to be the first candidates for seasonal updates each year.
3. Although many of my items will play nicely with each other because I have mostly neutrals, there is usually one combination for an item that makes me feel happiest. I think in the future I will be content with being able to make one or two great outfits from an item, rather than seeking versatility at the expense of a lower level of outfit happiness.
4. I like variety in my silhouettes. I was hoping that the elements of a uniform might emerge from this exercise, but what I have discovered is that I have high happiness for a number of different silhouettes. But I think that will be OK. Claire (I think) talked about "1 and done" for her item choices and I think that concept, in combination with points 1 and 3 will actually work for me.
Silhouettes
-pencil skirt and loose top
-loose pants and cropped top
-A-line skirt/culottes and various tops
-shorts with a trapeze top
-shift or trapeze style dress
5. The outfits I feel best in are both structured and feminine. I think part of the reason I have re-embraced shorts this season (apart from the weather) is the structure that exposing some skin provides. It allows me to wear loose and waist-surrendering tops without feeling sloppy and boyish. It also explains why I have fallen out of love with skinny pants - I need more femininity than I feel they provide for me.
One of the unexpected and positive outcomes of this exercise has been that I have been able to be much more thoughtful and circumspect about what comes into my wardrobe and much more aware of what I actually need as opposed to what I think I might need. As a result, I have been able to implement the "fewer but better" concept that many here adopt, and have put my clothing budget into buying a few pieces from Australian designers.
I would definitely recommend daily outfit photos as a way of clarifying your wardrobe planning issues.