Sperry® Cold Bay rubber Chelsea boots

If you're craving a boot that is nearly impossible to put on and take off, then this is absolutely the one for you! Without socks you might have a prayer, but you'll be pushing the insoles back in every time. (And and why are you wearing cold/wet-weather boots without socks to begin with?) With socks of any kind, you're finished, my friends. There is zero give to the opening of the boot, so it's like pushing your foot into a garden hose. It can be done! Oh, it can be done. But at what cost? Taking them off, forget it. Your sock is staying in there whether you want it to or not. I've bought many dozens of shoes from Sperry over the years. This is the only one I loathe. J.Crew made its own duck boot in 2004 or 5. It was perfect. I even wore it around the office. More of those, please!