Work boots: Well the obviously answer is that if he is rocking a hammer and a hard hat and has paint blotches on his arm, he is more than likely in construction of some sort. However not every man with a pair of Trees (Timberland boots) is Bob the Builder. Work boots were once popular in 1990s around the time when Onyx was slamming and Naughty By Nature was asking if you were down with OPP. Although they have now pretty much faded in obscurity, the style of rocking a fresh new pair of Trees is still very much relevant with a group of men. I have christened them young old heads. These men, who range in age of 30 to around 40, have a fondness for the “good ole days,” when men were outwardly roughed and free from the restriction of skinny jeans and smedium t-shirts. An era when all you had to do was throw on a pair of Trees and a Randall Cunningham Jersey to be considered fresh and clean. Work boot guy could also be considered a good catch for ladies looking to settle down into something more permanent as he is certainly beyond chasing trends or looking to upgrade into a shoe more fashion forward.
One caveat: If he is pairing his work boots with a long t-shirt then he probably is a young-old head drug dealer. In that case, call the police before he shoots up the block.