Is there any pair of boots more iconic or more associated with fall and winter style than Timberland boots? It’s a question that’s up for debate, sure, but for hard-working casual style across a variety of seasons, Timberland boots, or “Timbs,” are always a safe, stylish, and classic-yet-modern bet. And yet, there’s also a debate over how to wear Timberland boots. When we think of the brand, we think of the iconic “yellow boots,” the lace-up work boots designed to be worn in so many ways beyond just a day’s hard work.
Timberland’s signature style is a stalwart in popular culture, kind of like an even cooler version of another instantly recognizable pair of fall and winter boots (L.L. Bean’s Bean Boots, anyone?). Both belong in a well-rounded rotation, but Timberland has an effortlessly cool design that they’ve not changed all that much, other than to amp up the comfort, the sustainability, and the occasional collaboration revamp with new colors and branded detailing. For now, we’ll dive into how to wear Timbs, from lacing to styling tips and seasonal trends. There are endless options, so pay close attention: You’ll pick up more than a few go-to tricks this season.
How to style classic Timberland boots
The most commonly seen form of men’s Timberland boots in the wild. The classic premium 6-inch waterproof boots in wheat nubuck, of course. How should you wear these instantly recognizable boots? We’d say any which way you want because the sky is the limit. Some prefer to wear the boots with the original lacing design out of the box, while others prefer tight lacing all the way to the top. Lacing Timberlands is all a matter of personal preference.
That being said, Timberland boots are more rugged and are best worn with dark indigo, black, or faded light wash jeans, with your jeans cuffed and then rolled (opt for about a cuff of between one to two inches). The cuff-and-roll technique can be used to roll your jeans all the way above the padded collar of the boots, or else up near the top of the tongue. This shows off the boots and lets them do the talking. Because you’re teaming jeans with boots, opt for a more casual or rugged pick-up top, too, including one of the best puffer jackets when it gets cold. Think blue jeans and a light blue chambray shirt, or a long-sleeve henley, a bomber jacket, and black or blue denim. When in doubt, keep it simple and fresh.
How to style different colors of Timberland boots
The thing with a style like the premium 6-inch waterproof edition of Timberland’s famed boots is the variety you get with each pair. The rugged, easily wearable silhouette comes in many different colors and designs, including crisp white, sleek black or hard-wearing, rich brown leather. Brown leather Timberland boots can be worn in a bit more of a dressy fashion (more on this later), even with straight-leg gray chinos or gray or blue denim.
The thicker design of the work boot style means you can also add heavier layers on your top half, like a shearling jacket, a thick flannel shirt, or a shawl cardigan. If you opt for brown leather Timberlands, think of them like any other pair of rugged brown leather boots. White Timberland boots, on the other hand, are a bit flashier, so tone them down with black denim and a simple gray cotton henley and olive field jacket for a nice touch of contrast. Team your black Timberland boots with toned-down blue denim or gray work pants, then feel free to add a bold graphic tee on your top half for a pop of color.
How to style different types of Timberland boots
When you think of the long-running New Hampshire-based brand, perhaps the 6-inch boot is the style that comes to mind the most. Timberland has gone all-out in recent years to deliver styles that pay homage to the classic, but in a way that’s more slimmed-down, sleek, and dressy. They make unlined leather chukka boots and Chelsea boots, but it’s pairs like the Port Union Waterproof Boots
These are a more sleek version of the 6-inch boot style, with a thinner toe shape, a comfortable SensorFlex outsole that literally moves and flexes with your foot, a waterproof design, and rich tan nubuck leather. The tan nubuck and thinner design make them ideal to wear with cuffed gray wool trousers, a chambray shirt, and an unlined navy cotton blazer for high-low style.
You can also dress them up even further with a tan herringbone wool blazer, a white henley, and Donegal wool trousers for a rugged business casual style. You can use that same combination to great effect with Timberland dress boots and chukkas,
How to wear Timberland boots for fall and winter
Staying on the cutting edge of style and design is but one of the reasons Timberland has built a devoted following across the globe. And you should certainly take it upon yourself to wear your new favorite boots in an on-trend way for the seasons ahead. These boots go well with other go-anywhere styles. Leave the work pants at home and opt to wear your boots with either slim joggers or denim rolled above the boots to really showcase that design (as we said earlier).
Look for edgier colors like black or fall-ready shades like tobacco to let the boots stand out stylishly. Feel free to add layers on your top half, be it a henley underneath a denim shirt (underneath a field coat), and throw on a navy beanie for added warmth. A bracelet to complement your watch is always a solid bet, but again, the classic-yet-fresh premium 6-inch waterproof boots in wheat nubuck should really be the star of the show.
How to dress up Timberland boots
While it might seem tough on the surface to dress up Timberland boots, it can definitely be done: It’s all about mixing and matching the pieces you’ve got in your rotation, though. Timberland boots are all about embracing high-low style. So, think straight-leg navy chinos with a short-sleeve blue chambray shirt, a look that’s ready for the drafting table or the factory floor. If you do opt to wear Timberland boots with a suit, it’s all about keeping things easygoing. Look for a suit with a more relaxed (but still tailored) cut, with minimal padding and soft cotton or flecked wool fabric.
Do as the celebs do and mix it up a little bit: Think of an unstructured suit, a merino T-shirt, and your trusty Timberland boots (especially if they happen to be dark brown leather as we mentioned earlier). Skip the suit you’d wear to the boardroom, and opt for something breathable and made with stretch fabric, especially navy to really let your footwear choice shine through. As easily as you can dress these boots up, well, they can also be dressed down in a big way.
What makes Timberland boots so popular?
We’ve established that Timberland boots go well with just about any style, and they have a classic look, but just what makes them so popular?
For starters, they’re designed for comfort. After all, the boots are intended to be work boots, worn for long stretches at a time in tough conditions — if they weren’t comfortable, they would not be very useful. So, Timberland made sure the boots were comfortable as well as durable. According to the company, most Timberland boots are designed with suspension technology that provides arch support and helps prevent your feet from getting tired after wearing them for long stretches. The boots also have heavy-duty outsoles to provide grip and traction and midsoles that provide additional support, so they are best for all-day wear.
You may ask, what does all this mean? Well, it’s easy, you might not be walking around a construction site all day, but no matter where you go, your Timberland boots will keep you comfortable while looking stylish at the same time.
