Great question, Claudia, and thank you Vildy for your answer, which is along the lines of mine (only more interesting!).
I have an idealized version of my life in my head (still very realistic, except I have much better hair), and start by imagining what I would wear to various events. So, for example, I have a bridal shower IRL that I am going to next month, and I try to imagine in my ideal life how I would dress for that. (In my ideal life, I've already got the perfect wardrobe worked out). Then I'll see if I have any items in my closet that I can use to make up the outfit, and get the closest I can.
Imagining my ideal life, having already figured out what pieces work best for me, has helped me identify what pieces currently in my closet are definitely not me, so I can purge them. It's given me ideas to try things I might not have IRL, like more heels. When I see something in a store that catches my eye, I think, would this work in my perfect life? If so, how would I wear it? And that tells me if I really love the piece, or if it's something I think I "should" get because it's practical, but I'm not excited about it.
The truth is, when you work at home like I do, and nobody around me seems to be interested in clothes or shopping or putting outfits together, it can get pretty discouraging. At the Starbucks in my town, most of the women come in dressed in what they wore to the gym. Like Vildy, I feel good dressing as if I just came from somewhere, or am just leaving for somewhere, full of possibilities. Maybe I'm wearing a skirt, and maybe not, but I'm definitely not in my old sneakers and yoga wear, cause in my ideal life, I wouldn't wear those except to yoga.
I hope this makes sense in the telling.
This forum has been so great because not only are you all excited about clothes and shopping and being creative with outfits, but you also encourage everyone in finding their own ideal style. I'm a member of Team Dressed Up and Team Girly, and it's hard to find that balance between being true to myself, and looking silly in suburbia.