Do I Need to Wear Shoes When I Skate?Yes, you do! Unless you have incredible callouses on the bottoms of your feet, I would recommend wearings shoes. You know what, even if you DO have super tough feet - wear shoes! There is just so much that can go wrong while skateboarding that, without shoes, you are just asking for it. I mean, if you really want to, it's your deal, but I suggest shoes!
This question comes up a lot with longboarders. I have a buddy named Kyle who, in the first week of learning how to longboard, decided to ride wearing flip-flops instead of shoes. Bad idea. His hand looks like hamburger now, and he's going to have a large nasty scar on his elbow. Plus, as a bonus, his brand new flip-flops are completely destroyed. It's funny now, but in all seriousness, he could have been hurt badly. Wear shoes.
But do I Need "Skate" Shoes?Ah. Here's where it gets dicey. Technically, no, you don't need skate shoes. You could wear army boots. But the point is, skate shoes are made to help you skate better. And it's true - they do help. Skate shoes have flat, grippy, and usually extra wide soles to help you hold onto your board better. Those puffy moon-boot style skate shoes have extra padding on the sides and the tongue to help protect your foot when doing technical tricks. The thin classic style skateboarding shoes help improve how much you feel the board while doing tricks, so you can pull off even more complex tricks. A lot of skate shoes now have reinforced side panels to help with ollies, or have extra padding around the heel collar to help hold onto your foot. Some have extra flaps to help protect your laces while you ollie. Some are made from extra strong leather, or have other special features.
All this to say, actually "Skate Shoes" do help you skate better. But you don't need them. If you can afford a pair, I say go for it. If you can't, then don't let that hold you back from skateboarding. Just slap whatever you DO have on your feet, and get out and ride!