Suz - I think preferences in style and comfort zone are a lot like friendships. I know many lovely women, very pleasant, but on some basic level I don't connect with them. I call it the "cosmic click." You know immediately when you meet a truly kindred spirit, they just "get" you and you "get" them. I think it's the same with art, literature, clothing (after all it's wearable art!). I think that connection is actually a recognition of "self." This is me, this gets me, on an almost primal level. I don't think it's irrational so much as inarticulate. Like the romantic poets notion that poems are "emotion recollected in tranquility." We find it difficult to verbalize about things that create strong emotions, we can only verbalize once we distance ourselves from the emotions they engender. Why does black sing the sirens song for me? I think I could write a book about that! Black "gets" me so many levels - not just flattery to my complexion, but on emotional levels of expressing my message. Black provides the negative space that I can fill. It embodies the qualities of mystery, quietness, intelligence, formality, and simplicity. It is a powerful and can be conservative, edgy, avant garde or elegant in turn. These qualities are the message I wish to convey - these things are me. Brights would not convey the same message. Those pieces, patterns, colors, textures that convey my message become me, what conveys an alternate message would be "outside the comfort zone" because there would be a disconnect between self and "the message", they would not convey "me." Gosh, did that make any sense!!

For this question, I tend to think of things that are fashionable but outside of comfort zone. And maybe also not "obvious" things like, midriff-baring cropped tops in middle age or short skirts--because these things might vary.

Very pointy toes come to mind, and it's not just physical comfort. I have a poison eye for them as they somehow connote witchy-mean (sorry, fabbers) and also an extreme of not-anatomic shaped clothing--even though of course neither are almond or oval toes and if I really were focused on foot anatomy I'd have to wear Earth shoes or something. So it's that it is more extreme and that it says to me (to me, for me) that I am making a really intentional fashion choice. Hard to explain.

Any really expensive recognizable designer type brand or logo is also outside. But here's where i would have trouble--if it were a super-fit, super quality item (and not just brand hype) and I found it thrifting or e-baying (which I don't do) for a crazy low price, then I'd really be torn, because I'd have to deal with my reality of not having paid any more, and maybe less vs. caring about what others might think. So this can be a problem even with better-quality clothing at sale prices if it is somehow really recognizable, but can be mitigated fewer total items and re-wearing and re-mixing.

High heels, meaning 4" stilletto pumps and sandals come to mind even if I could wear them. They are so not part of any crowd I'm in (except my youngest DD!) and they don't fit the rest of my style either. Now, it would be fun to see if my answer changed if I really could wear them! And I do have HEWI's of comfortable medium-high chunky heels ( 2-2.5", woo-hoo!) and interestingly, just about nobody I'm with ever wears those, either, but I'm okay with that, on occasion.

I hear you on leather Moto jackets Suz- I have tried and returned too.
My K/R yesterday springs to mind also. I like to be comfortable with the cost of an item as well as the fabric, fit and style, but I am willing to spend a bit more for the right piece in the long run.