How many pairs of shoes does one man really need? Three? One? Fifteen? Thirty? (Please let this be the one post the permanent roomate doesn’t read.) The answer to the original question is different for each dude because it all depends on purpose. You need shoes for work, play, beach, moonwalking, outdoor festivals, the vegan chick, etc. We don’t live in the 1950’s anymore. If you’re worried about someone commenting on your kick collection, just co-habitate with someone who has more. If the constant nagging just isn’t worth it, you need to find shoes that fill more than one void in your life. These are those shoes. Equally boot and sneaker – and composed of oiled canvas and rubber – the Keds Champion Chukkas tote the line between business and casual. They will also look good with whatever pants you’re wearing: jeans, pants, shorts, trousers, or nothing at all.