The classic six inch Timbs come with seven eyelets (the holes you run the laces through) on either side of the boot. If you’re going for a loose laced boot, undo the factory lacing, and re-lace; making note to skip every other eyelet. This also means stopping before the topmost eyelet. There’s no hard and fast rule however, so if you find this is either too tight or too loose, add or unlace eyelets accordingly.
Another thing is that it’s widely understood that Timbs look better when they’re not tied tightly around your foot, but instead worn loose. Does this mean you need to fall out of your Timbs with every step? No. But it doesn’t mean that your boots should be choking your ankles either.
While we’re talking Timbs, tongue placement is key. Before your mind wanders to the inappropriate, the tongue on Timberland boots is an issue that’s more up to personal taste than anything else.
Regardless of what you decide to do with the boot tongue, your trousers should fall behind the tongue. Whether you’re stacking or cuffing, avoid placing your pants over the tongue. Depending on how you lace up your boots, you can either let the laces lie behind the tongue, in front of the tongue—or you simply fold the tongue down, and keep it moving.
