First, I would try to figure out if the weather/climate isn't cooperating or if the item is for my fantasy life. Then, I would try to determine if it is a styling issue or what the problem is.
Awhile back, I bought a (cheap! F21!) clutch just to try out that style. A few months later, I passed it on to DD because I determined that physical issues make it next to impossible for me to hold a flat envelope style clutch and I hate the look over my shoulder plus it doesn't really stay put. Am I completely off clutches? No. But I know that I need to have a baguette shaped one (hard to find) or one with a wristlet (starting to get easier to find). I also would need to commit to carrying less. Right now, I keep my baguette shaped clutch in a larger shoulder bag that I use most of the time. I still love the clutch, though!
I am quite willing to skip trends I don't like or don't work for my body. I saved quite a bit of $$$ when all the tops and dresses were empire cut. Flowered dresses are all over the place at Nordstrom, and some might even fit and look nice on me. But for some reason, they *feel* too feminine to me. Must be post-menopausal lack of female hormones. So I will leave that look to others including my girly daughter.
It is interesting that you note that sneakers you bought feel too RATE for you. I am drawn to some very RATE looks like moto boots as well as a few very refined looks. But when I think long and hard, neither extreme ever feels quite right on me so I need to avoid both so as not to make [more] shopping mistakes.