"I am a sucker for classic subculture looks so, of course, I am going to co-sign Tims. If it was 1994, this dude would make you a mix tape with Mobb Deep and Jodeci, which is a good look. Depending on how tight or loose his pants are, you can get a pretty quick read on his sartorial vibe. Many a fly dude have built the foundations of their outfits on Tims."
Timberland Men's 6 Inch Classic Waterproof Outdoor Boot, $129.95, available at Infinity Shoes.