SW&D is unfairly pigeonholed for only liking "one look," but there is some truth to the groupthink perception. Side-zips would look better here, but that doesn't mean other footwear wouldn't, too. It seems lazy to often default to the safe suggestions, even if they would improve the fit. How many times a week is someone in this thread told they need a "sluttier tee" or side-zip boots? Casey is wearing an aggressive jacket, but I think the tee looks fine. It's certainly not morbidly out of place.
The caveat with commonly suggesting items from a very shallow pool of options is that it does risk taking some of the creativity or personal flair away from those who contribute pictures of their fits here. Dozens of people here do their own thing (and well), yet it can't be argued that a lot of folks here aren't easily influenced by suggestions thrown their way. Again, this isn't always a detriment to the quality of someone's outfit; quite the opposite, usually. But again, where's the appeal of more and more contributors here dressing similarly?
This isn't all directed toward Casey or the comments the ensued, but rather a trend around here that's developed and intensified over time.