Thank you so much for the replies! I am feeling a bit less frustrated now. A lot of answers were very helpful and got me thinking more straight.
Joy - you are right I need more edgy footwear, since it's often the only item seen when I'm out until I take off my jacket. My bags are pretty plain too.
Tracina - I think you make sense, that maybe my WIW are a lot more on the safe side then these pins, and I feel that way myself, just trying to decide or find what will take them up a notch to what I want.
Ceit - the assymetrical black top is also Helmut Lang, I do agree that it's often small details that set pieces apart, which is usually what I like in the first place. I often have time finding alternatives that work as well.
Suz - you have a lot of wisdom for going through your own style journey. Hopefully you are right and I am close to a breakthrough! I think you are right, I will try to copy a few pins closely, just to get myself thinking and using my own clothes. I also agree that it is really hard to translate some looks to cold weather. I mean it's not like we wear open jackets in winter, or rolled pants.
Angie - thanks for chiming in. I do agree that pins should be inspirational, which is kinda why a lot of mine don't translate well to cold Cananda weather. I tend to pin what I like and go, and hope to draw from it later. That's the part I'm struggling with now. I do have some pieces that don't go as well, mostly the colorful ones, and I'm not sure why, but I love overall dark outfits, but tend to be drawn to colorful pieces sometimes.
Beth Ann - like I said to Angie, some of my color pieces stick out a bit, but I can still try to incorporate them into my look. I love darks and neutrals, but color sometimes as well.
Mary, Sona, traceyLiz, SarahA Shannon and Isis, thanks for your support!