I think that every bloke should have a pair classic Timberlands in their collection.
Not the very light wheat coloured boot which I think are a bit chavvy, but the darker nubuck rust coloured ones or chocolate brown leather.
I've had a pair on the go for 20 years now. In that time I'm currently on my second pair, and these are seven years old and just broken in. I've got the darker nubuck boots, and although I've got plenty of other boots, these are the first I go to when the weather is particularly crappy.
Significantly cheaper than redwings too. As a previous owner if redwing boots, I don't get them at the price point they are now asking.