Errrrr...dunno where the squeaky thing comes from, but I noticed that once it has been broken in, it no longer squeaks as much? Now for the shoes, these are a classic. They are very comfortable. If you're used to wearing converses then, you'll be fine with these as they have padding on the heel unlike the converse. My brother wears these as his go-to shoes—it's been only a few weeks, so let's see how long these will last. But as it stands, they are great. He has also been getting compliments over them. He tried a shoe in store (size 8) and then I ordered the same size here online, and it fits him well—no pinching, or hitting the edge of the shoe with the big toe. Fits really well.