I wonder if you could get somewhere by exploiting the middle ground between "naturally stylish, enjoys shopping" and "hates shopping, same ratty t-shirt," namel

I wonder if you could get somewhere by exploiting the middle ground between "naturally stylish, enjoys shopping" and "hates shopping, same ratty t-shirt," namely "kinda enjoys successful shopping, but is terrible at it." I'd think of it as being like those services where people go and put together a couple weeks' worth of meals: those people don't hate cooking, they hate the results when they fail at cooking. Personally, I enjoy when I find something that fits right and looks good, I just have no idea how to go about making that happen reproducibly.