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There are hundreds of different styles of trainers, I find teenage lads seem to favour these huge Nike Air type, I wouldn't personally wear them. But to answer your question, trainers are comfortable if I'm walking about all day. Not sure I would wear shoes with shorts in the summer.

For work it's boots or trainers depends on what I'm doing. I wear trainers when I'm not working, but wear boots when the weather is bad or if I go walking. Very rarely wear shoes.