How to Wear Timberland Boots and Not Look Totally Ridiculous

From expertly lacing Timbs to wearing tapered pants with your boots. Here's the best styling advice & tips on how to wear Timberland boots all year around.

How To Wear Timberland Boots
Complex Original

Image via Complex Original/Liam Eisenberg

How To Wear Timberland Boots

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). 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

How To Wear Timberland Boots

When In Doubt, Wear Tapered Pants With Your Boots

How To Wear Timberland Boots

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

How To Wear Timberland Boots

Timbs Are Big, Size Down

How To Wear Timberland Boots

Every Day is Timbs Season, But Maybe Reconsider

How To Wear Timberland Boots

Waterproof and Take Care of Your Timbs

How To Wear Timberland Boots

Choose Your Timbs Wisely

How To Wear Timberland Boots

Keep Your Pants Behind the Tongue

How To Wear Timberland Boots

But Can Timbs Can Be Worn As Formal Attire?

How To Wear Timberland Boots

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