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My ds wears football boots to play in at the weekend. The ones with little plastic studs. They're great in the rain,got good grip to them,smarter than trainers but possibly not the look you're going for! He loves them though, he's 6.
Depends on the season, flipflops/sandals, crocs at the moment, then ballet pumps, canvas shoes etc then boots in the winter, wellies in the snow or if you know it's gonna be wet n muddy, then back to pumps for spring
DS currently wears his wellies an awful lot. He also wears canvas sandals (his sister's blue flowery ones, he doesn't give a shiny shite about whether things are for boys or girls), sort of utilitarian walking sandal things and brown leather lace-up boots.
At that age mostly mine wore wellies he then progressed to Airwalk skate style shoes (suede, breathable, hard wearing, sturdy, cost about £15-18 a pair, Velcro straps) he would prefer to have Vans or DC instead of the Airwalks, if I can afford them! We avoided Converse as his feet were previously wide, might try them again now they've narrowed down a little.
My DS has leather casual shoes from Hush puppy (he has wide feet). I don't like trainers either, I think they can make little boys look a bit 'tough' somehow. At the mo he's living in crocs and leather sandals. He also has wellies (and trainers for sport).
My 5 year old has hi tops with a helpful Velcro strap at the top from H and M. He has trainers/crocs/wellies too. He chose some Minion ones and navy ones to take to Cornwall next week. Very reasonable and bit wider than Next for his fat feet