I got my first pair of topsiders this spring and very quickly fell in love with them. The first week or so my feet received a fair share of blisters from bear foot wear but they quickly came to be the most comfortable shoes I owned. My affinity for them, at least aesthetically started is rooted in my fathers longterm commitment to the brand. The pair he currently owns was purchased at a Ontario Place boat shoe while I was in grade one, so about fifteen years. This is a testament to the longevity of quality footwear when you are willing to do basic upkeep in addition to the occasional repair.
My pair quickly wore, as I wore them near daily, for three months throughout the summer. They started as what Sperry calls sahara, or what is a much lighter almost sand tone. They, like the desert boots, have darkened significantly with the application of Dubin oil.
I terms of style, they are considered to be an American classic, so they carry a baggage of heritage. I like that I can wear them with a variety of things from jeans and a t-shirt to chinos and a blazer. They, like most of my other shoes wear in with a desirable character and I find tend to look as good scuffed up as they do out fo the box.