Posted March 1, 2018

How To Cuff Your Pants with Your Timberland® Footwear

By: @bluecollarprep

How to cuff pants

Ever since the 90s, I've been a fan of Timberland. It all started with that classic yellow boot. All my favorite celebs during that time were rocking the boots, not to mention my entire group of friends - it was definitely a style that everyone loved. Now, 20 years later, the classic yellow boot is still a staple for Timberland, and for me. I have an entire closet of shoes, half of them being boots, and I’ve always had Timberland among my collection. Aside from the classics, my taste has expanded over the years, and I've added quite a few of their other styles to the mix!

I’ve teamed up with Timberland to show you how to style and wear 3 different footwear silhouettes as the seasons transition – sure to handle even the most unpredictable weather.

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.

When it comes to cuffing your pants with different styles of footwear, you just need to play with the cuff to see what works. Whether it's a classic double cuff, a single thicker cuff, a half-way sloppy cuff, or 90s tight-roll, most of the time my goal is to aim towards my pant leg sitting right at the top of the shoe or boot. If you’re going for a more cropped look to show off your socks, like I did with the boat shoes, a few inches above is a good place to hit. 

If you liked this article, you’ll love this one on how to clean and protect your favorite Timberland® boots and shoes.