This has been my teen son's go-to casual shoe for a couple of years, so I've bought 5 or 6 pairs since he's started wearing these! He has worn these both laceless (laid-back summertime look) and with the laces (serious schoolday look).<br /><br />These sneakers have a preppy vibe if you wear them with madras shorts, and they're less nerdy than classic leather TopSiders. With blue jeans and a a tee or flannel shirt, they look more skater-ish. Either way, a fashionable but comfortable shoe option for a young boy.<br /><br />As for fit: these are roomy enough for his wide feet, and sizing has been consistent for all the pairs he's had. I've thrown these in the washer and dryer and they came thorough fine. Unlike other sneakers like this style, these Sperrys do not separate where the canvas meets the rubber sole, even with a lot of wear. Great value!