The thing is, these items individually are all really nice. I was decked out in a lot of money. Fendi, Rag & Bone, and the Banana Republic coat isn't considered high-end, but it was still $300 for the coat because of the materials.
The thing is that they all look terrible mashed into one outfit. There is nothing resembling a color scheme, it's too many different textures and patterns, and it doesn't make sense. I think I was just really trying to look "Seattle"-ish here. Like, "Hey, I totally don't care about style or fashion and just threw this on and it's fashionable anyway" except for the part about it being fashionable anyway. If I wanted to look like I gave zero fucks about my clothes, then I definitely succeeded. If I wanted to make my designer clothing look like I got it out of the clearance bin of Goodwill, then I succeeded there too. I managed to make my expensive clothing look really cheap by not styling things well, or pairing the right items together.
Note: I do still own a lot of these items, and definitely wear them very differently now!