How to Wear Timberland Boots and Not Look Totally Ridiculous

Oct. 30, 2019

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. While the boot was attached to a rather controversial collection by A.P.C., the fact that the Parisian fashion brand used the shoes in their collection proves that future fashion-centric collaborations seem more reality than fantasy.

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 wearing an outfit that's too dressy with them. While there are several ways to rock your Timbs—from loose lacing to tongue folding—we're here to show of the best ways to pull off a pair of the six inch staple, and help you care for your boots too. This is How to Wear Timberland Boots.

Tightly laced Timbs are for nerds.

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. For a modern styling, the best type of pant to wear is going to be tapered. Whether you're rocking tech fleece or skinny denim, 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 #NTDenim, going with a baggier bottom 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 a foolproof way to wear Timbs.

Noting the above, we 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.