Shoes tend to be the biggest problem - pun intended. I'm not intending to get all stereotypy, but from personal experience, women tend to think to bring along multiple pairs when traveling: day, night, beach, casual, exercise, etc. At least my ex did. Me? I've never gone in big on shoes, and I'll be addressing this with a single pair of shoes that can be used across all situations: running shoes. They are only optimal for running (which I plan to do, definitely), but, and I stress this, can be used in virtually all the situations I envision myself in. I can sightsee and visit museums, I can walk the beach, and I can go out to restaurants wearing them. Since I'm not taking any kind of even semi-formal wear, upper class restaurants where I'd need something a bit more classy, are not on the docket at all. I'm also taking along flip-flops, because my dogs need to breathe.
I'm addressing the problem of bulky outerwear with a decisive two-pronged approach. The first prong is the easiest: since where I go and when is completely under my control, I'm not going to go where it's really cold. Boom, done. The second prong on this is to go with multiple layers: layer one is a Houdini windbreake that is ridiculously compressible. Layer two is a puffy jacket. Not an expensive one, like a Patagonia, but one I've had for a few years, and quite serviceable. Layer three is a rain jacket. I spent some coin (for me not my Witcher) on a Nike Hypershield Flash a few years ago as well for quality and visibility. (It appears this is no longer available. Huh.) When I'm out there in the dark, I look like a running disco ball when lights hit me.