There's no such thing as the perfect item of footwear; no matter how comfortable you might find your trainers or how good you think they look, someone will always think the opposite.
I can't help with issues of comfort, except for recommending the softest, nicest leather you can find in your budget.
When it comes to aesthetics, though, my best advice is to keep it simple. Every man should have at least one pair of trainers which can be worn with the vast majority of his clothes; a simple, smart-looking pair of trainers is the only option, which is why Converse All Stars are so popular. They look as good with distressed jeans (*shudder*) as they do with chinos and a shirt.
I have a pair similar to the Pradas above and they're great, from the soft leather to the fact I can wear them with almost everything in my wardrobe; despite their seemingly non-descript nature, I'm constantly asked where I found them. Always pick black or white too since they're the two best options for versatility; the reason I chose black was that they never look dirty - a big plus if you want to wear something regularly.
Rest assured, I'm all for outrageous footwear, but it's best to get a daily workhorse out of the way before pursuing one's more creative tastes. Patience, my friends, I'm new to this...
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