How To Cuff Your Pants with Your Timberland^® Footwear

The first style is the Original Yellow Boot. I styled it with fitted denim and went with a traditional cuff that sits right around the top, just above the boot. This is how I style most boots -  the simple double cuff just seems to look the best because it allows your pants to sit right above the top of the boot. I wore a distressed black hoodie, topped with a plaid coat and some clear-framed aviators. I kept the laces untied and on the looser side to play up a grungier vibe. You could also style these boots in a more casual way – still with fitted jeans, but add a flannel or puffer jacket for another great look. But no matter how you style it, I suggest a traditional cuff that sits right at the top of the boot.

Next up, the Men's 2-Eye Boat Shoe. I love wearing boat shoes! They are super comfortable, and despite what anyone says, I’m in favor of wearing them year-round. For this look, I picked a pair of looser-fitting jeans and went with a fast, super-casual, somewhat sloppy half-cuff. Every cuff doesn't have to be a double cuff, or even a perfect cuff. These jeans have a slight crop to them already, so that added half-inch cuff was just what I needed to show off my boat shoes-and-socks look even more. I like how these boat shoes give my look a casual, yet dressy vibe. 

For the last style (and my wife's favorite), I wore the FlyRoam™ Leather Hiker Boots. With taller shoes or boots, sometimes the way to go is just ditch the cuff altogether, and go with a cropped pant. It gives off the same look as a cuff, but with a cleaner line. These navy cropped pants were the perfect length to fall right above the shoe, just where I like it. I kept the rest of the outfit simple in a combination of blues, with a neutral shirt. I wore a cream flannel, topped with a denim jacket, and threw on some shades. The color of the FlyRoam™ boots looked great with the blue denim.