Ever since the 90’s I’ve been a fan of Timberland. It all started with that classic yellow boot. From Wu-tang and all my other favorite rappers during that time, rocking that boot, to my entire group of friends, it was definitely a style that we all loved. Now, 20 years later, the classic yellow boot is still a staple for Timberland, and for me, a boot that gives me that nostalgic feeling. I have an entire closet of shoes, half of them being boots, and Timberland has definitely always been among my collection throughout the years. Aside from the classic, my taste has also expanded. I’ve added a few other styles and have also used their hiking boots for work quite a bit!
This season I teamed up with Timberland to show you how I styled 3 different shoe silhouettes and how to cuff your pants for each shoe!
The first style is the classic Men’s 6-Inch Premium Waterproof Boot. I think this is probably Timberland’s most iconic boot they make. I styled it with a fitted denim and went with a traditional cuff that sits right around the top or right above the boot. This is actually how I style most boots…this simple double cuff just seems to work and 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 this plaid coat and some clear framed aviators. I personally like how the yellow Timberland boot looks with more of a street style. I also kept the laces untied and on the looser side to play up that grungier vibe. Even thought this is the look I went with this time around, I’ve also seen these boots styled in more of a casual way…still with fitted jeans, but with a flannel or puffer jacket and I think it looks great as well. No matter the look though, I suggest that traditional cuff that sits right at the top of the boot!
Next up…the Timberland Men’s 2-Eye Boat Shoe. I love wearing boat shoes! They are super comfortable and despite what one says, I am in favor of wearing them all year round. Typically, I’m a no-sock guy – even in the winter sometimes. (don’t judge me LOL) But, since this boat shoe does have more of a summer look to them, the way I made them winter-ready is to actually throw on some socks and show them off. This time I put on a pair of looser fitting jeans and went with a loose, somewhat sloppy, half cuff. Almost like I wasn’t sure I even wanted to cuff my pants, kind of cuff LOL. Every cuff doesn’t have to be a double cuff or even a perfect cuff. Hey, sometimes I throw in a 90’s tight-roll from time to time! 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-shoe, sock-look even more. I like how the Timberland boat shoes gives my look a casual, yet a tad dressier vibe. Timberland also has these shoes with a rugged sole, that is also a perfect option for winter if you’re not comfortable wearing the traditional boat shoe during this season. They are actually next on my wishlist!
For the last style and my wife’s favorite, I styled the Timberland FlyRoam Leather Sport Chukka Shoes. Sometimes the best way to choose the right pants that go with a taller shoe or boot is to 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…so I went cropped this time around. These chukka shoes look more like an athletic high-top sneaker than a traditional chukka shoe that you might think of when you hear the word chukka. (it actually made me google the word Chukka LOL) When I wear this style shoe, I don’t really like the way regular length pants look at the top of the shoe. The pant leg bunches up and it tends to start looking bulky, and sometimes when you add a cuff, you are just adding to that bulkiness. These navy cropped pants that I went with were the perfect length to again fall right above the shoe, just where I like it. I kept the rest of the outfit pretty simple and just did 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 Timberland Chukka shoes looked really great with the blue denim.
I think it’s safe to same I tend to cuff my pants more than I don’t, no matter what style shoe or boot I’m wearing. 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 90’s tight-role, most of the time, my goal is to aim towards my pant leg sitting right at the top of the shoe or boot…or a few inches above, if you’re going for that cropped boat-shoe look like I did!
Check out my feature on the Timberland Blog!