I've really benefited from reading all of your thoughts, and I thank you all again for contributing here.
This exercise forced me to dig deeper into why I am answering "no" to all three questions , and then to come up with what it is that I'm looking for and cannot find.
1. I have lied to myself by constantly proclaiming (on this forum) I dislike shopping. I like it. I love fashion , fabric, merchandising, colour, ideas, trends, classics, quality, all of it. I've been sewing since I was a 10 year old. Designing, tailoring, learning , reading, studying and working in fashion since the age of 15. However.....it usually functions as a way to fill an emotional /psychological need, and has so my entire life. I recognize it, but haven't been successful in finding a way out of this behaviour. The only thing I dislike about shopping is coming away feeling ugly (internally and externally) because nothing fits that day.
2. I spent a bit of time this morning looking for images I could post here to show what my "ideal" style would be if I had access to it. What was immediately apparent is that everything I picked was very, very simple, often monochromatic, and quite understated. Not plain , because cut and design and fabric are everything, but not shouty and silly and cheap looking either. Think Anine Bing, Jenni Kane, Eileen Fischer, Everlane. Linen, fine gauge wool, silk, cotton, jersey. And not a lot of colour. Basic pieces - blazer or sweater, tank or t or blouse, and jeans/pants . Accessorized with stand-out shoes, jewellery and bag.
3. BUT - for some reason , I come home with fun pieces in colours, prints and silhouettes that are very far away from the look I think I want . Stores here do not have beautifully cut linen tops, unique jackets, drapey vintage-y t-shirts, architectural dresses, great pants.......at the price I can afford to pay. I can't afford Anine Bing , Veronica Beard, Smythe or Jenni Kane, Iro, etc and only EF once in a while when it's on sale. Plus, most of these brands aren't available at retail here anyways . So I head to a store, get caught up in pretty displays, colour and pattern and friendly sales staff who look great in clothes like that and convince me that I do too......and come home with things that aren't quite what I want . I am extremely self -conscious , and am always fussing about clothes pulling on my body, sticking to my butt, amplifying my chest etc etc. All I want to do is recede into the background and feel comfortable, stylish yet sophisticated. Instead, I walk around feeling out of place, and too try-hard. Style should come organically, and show one's sense of comfort in their own skin .
4. I often pronounce that I'm only buying fewer and better. And then it never happens - because that "better" isn't here.
This is my conundrum, and I'm not sure how to fix it.
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