The sheer timelessness of Timbs can’t be overstated.
The work boot has emerged not only as a staple on construction sites and workshops, but is commonly seen on city streets, runways, and collection lookbooks. Back then, a rugged pair of wheat Timbs was one of the ‘90s most iconic fashion trends. Today, the boot has become a staple within streetwear. Special Timbs made in collaboration with brands like Supreme, Comme des Garçons, and Off-White have become coveted collectibles, while Timberland boots like the World Hiker or “Beef and Broccolis” have built its own cult following. The boot is also a New York City staple, something you can’t miss if you so much as walk down the street in the colder months (and sometimes the warmer ones).

The boot is also a New York City staple, something you can’t miss if you so much as walk down the street in the colder months (and sometimes the warmer ones). Timberland boots also offer more than just style. As shown on Hiking With Rappers, Timberland boots are also solid to wear while exploring the great outdoors.
If you have no idea how to wear Timberlands, this is where to start. It’s easy to get the look wrong with a pair of pants that are too baggy or an outfit that’s too dressy with them. Even some of your favorite celebrities need some coaching on how to adjust the boots’ wide leather tongue or how to lace them. Aside from how they’ll look, there’s also other important things to consider when wearing Timbs. Should you size up or size down? Can you wear a pair of Timbs in the summer? How do you make sure they stay waterproof in the rain? While there are several ways to rock your Timbs—from loose lacing to tongue folding—we’re here to show you how to pull off a pair of the six-inch classics, and help you care for your boots, too. This is how to wear Timberland boots.

How To Lace Timbs Like a Pro

Timberland laces make up a big part of your Timbs style. 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.
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.

When In Doubt, Wear Tapered Pants With Your Boots

We know that guys will read that headline and be up in arms but hear us out. To emphasize the boots, the best type of pants to wear is going to be tapered. Whether you’re rocking Nike Tech sweatpants or Amiri jeans, you want something that’s going to stack, or at the very least, fall within the collar of the boot.
Much like dudes who wear their Jordans with Evisu denim, going with a baggier bottom could awkwardly drapes across the boot. We’re not saying that tapered pants are the only way to rock the boots, but Timbs deserve to be seen—not covered by billowing bootcut jeans.
Oh, and before we forget about Timbs and shorts… tread super carefully. The only guy that can pull this off on a regular basis is Pharrell. 98% of the time, it’s a solid fail, but when done right, it absolutely kills.
Stacked skinny pants are also a foolproof way to wear Timbs. But we also know that some guys just aren’t down to let their denim (or other trousers) stack up on the collar of their boots. In the case of cuffing your bottoms, know this: if the cuff is wider than the collar of the boot itself, then try a different pant. We understand you’ll want people to “peep the selvedge” from time to time, but it’s not going to look right if you’re cuffed hem parachutes out from the top of your Timbs.

For An Old School Look, Go For Baggy Pants With Timbs

Some people aren’t fully comfortable with wearing tight skinny jeans with a pair of Timbs. Although it’s common to see jeans tucked into the 6-inch boot, ‘90s rappers have taught us otherwise. As seen on the likes of Biggie, Tupac, Aaliyah, and younger rappers such as ASAP Rocky, it’s completely fine to rock some Timbs with a pair of baggy jeans. So, for those who need some air around their thighs, go for it.

Timbs Are Big, Size Down

Without speaking for everyone, it’s advised you cop your Timbs at least one size below your normal shoe size. This is especially true if you’re planning to loose lace your boots. If you’re conflicted on where you’d fall on the Timberland size chart, or you’re the type of guy whose size fluctuates wildly between brands, size down. You can thank us later.

Every Day is Timbs Season, But Maybe Reconsider

Yes, Timbs could be worn all year—if you’re working in an environment that calls for it. We recognize that guys want to, and will, wear their Timbs all year round. That’s not necessarily a bad thing. But, trying to force a pair of Timbs on an 80-degree day? With shorts on? It might not be the best look.
While it all depends on how sunny Mother Nature wants to be, by early to mid-May, your Timbs should be hitting the offseason. Or you could just take a cue from George Costanza and wear them no matter what.

Waterproof and Take Care of Your Timbs

Are Timberlands waterproof? Well, like any pair of leather footwear, you need to treat the leather if you want the boots to come out of winter looking the way they did going in. Timberland claims the boots are waterproof, and in a way they’re right. But when they say “waterproof,” they mean that your foot will stay dry, and that water won’t enter the boot—not that the leather is actually going to repel water externally. Unless it’s specifically stated, you should expect that a lack of leather treatment will leave your boots looking less appealing.
Most chain shoe stores carry a suede protectant and waterproofer. When applying the protectant balm or spray, make sure to add about two coats, wait about 20 minutes between each application. Using a brush to work in the product should help. Overall, don’t be surprised if you see some discoloration—how you deal (or don’t deal) with that is up to you. But hey, Timbs are work boots after all. Treating them isn’t a requirement. Wearing them with a little age or discoloration isn’t really a bad thing. But if you’re looking to clean your Timbs, be sure to check out tutorials offered on the company’s website.

Choose Your Timbs Wisely

The notoriety of Timberland boots has gotten so big, that designers and collaborators have been able to produce colors that stretch well beyond the classic wheat. From Spongebob themed boots to The North Face Nuptse Timbs, the workwear boot is starting to see collaborations more commonly found on the sneaker market.
That said, just because you can cop doesn’t mean it’s to be done. We can respect experimentation, but if you’re on the fence (or you’ve never had a pair of Timbs before) we suggest starting with the wheats—or if you’re a fan of Biggie Smalls, the all black model.

Keep Your Pants Behind the Tongue

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 pants 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.

But Can Timbs Can Be Worn As Formal Attire?

The classic Timberland design is a work boot. With all of the inroads the company has made, not only into hip-hop, but fashion as a whole, we forget that the boot is just as impressive for its original purpose: getting shit done.
Like Red Wing, Viberg, or Wolverine boots, Timbs aren’t just meant for streetwear fans, and they shouldn’t be worn in just that style either. You’d be surprised at the flexible functionality of the silhouette. Much like your own wardrobe, don’t let your Timbs (or your desire to wear a pair) be pigeonholed by any particular style. Celebs like Jay-Z have worn them with long fur coats while Kanye West has worn them with Balmain jeans and luxurious camel wool coats. But maybe reconsider if you’re planning to wear them with a suit or tuxedo.

Image via Complex Original/Liam Eisenberg