Timberland boots are nearly synonymous with “rugged,” and they’ve become a modern classic in the world of casual footwear. But Timberland doesn’t just make boots. In fact, they also manufacture shoes, sandals and performance footwear for men, women and kids.

While most of their styles still convey that “rugged” feel, their casual line is anything but predictable. Check out the selections below to see a few of my favorite styles for men.

Timberland Boots and Shoes for Men
Top Picks in Timberland Boots and Shoes for Men

Or, take a look at my top Timberland Shoes for Women.

‘Classic 6″ Premium’ – The Definitive Style for Men

Here’s the boot that defines the brand. In fact, when most people conjure up a mental image of work boots, I bet a lot of them are thinking of this exact style.

The Timberland “Classic” is rugged, stylish, tough, and perfect for when you want to look like a manly man. But, you don’t have to be a construction worker to rock these boots. They’re a great match for jeans and a casual shirt, even if you have no intention of doing hard labor any time soon.

Of course, good looks alone wouldn’t make these boots as popular as they are. And, they are extremely popular, thanks in no small part to their construction, which features sealed seams; waterproof full-grain leather uppers; and rust-proof eyelets. There are also lots of comfort features built into these boots, with one of the most important being the specially-designed midsoles that allow you to stand comfortably for longer periods of time.

The wheat nubuck version (shown here) is so ubiquitous that you may not even be aware of the fact that these boots come in other colors and finishes, but they do. The black nubuck is totally intimidating and cool, while the olive green version is a little bit earthier — it also happens to be my favorite of the three.

Timberland Earthkeepers ‘Rugged Originals’ – Modern and Stylish

I’m crazy about this particular style. They have a contemporary, almost trendy look, while still being masculine enough for just about any guy to admire. They have all the usual comfort and construction features, but what I really love about these boots is the burnished uppers that give them a lived-in look. And, while the dark brown is nice — even a little bit different, it’s the red-brown version that I’m partial to.

Naturally, they’re the perfect match for jeans. As far as shirts go, I’d pair them with flannel, henleys, tees, or even a slightly-dressier button-down.

‘Wodehouse Lost History’ – Knockout Lace-Up Shoes

Easily one of my favorite styles of the season, these cap-toe oxfords from Timberland will appeal to guys who are after a really contemporary, trendy look; as well as those who prefer a no-frills finish and a classic style. They still have that rugged vibe that the brand is so noted for, but they’re just a bit more streamlined and refined than most of the label’s offerings.

For me, the most notable thing about these oxfords is the hand-finishing of the uppers. It makes these shoes look so delightfully lived-in, but not old or distressed. The cap toes are also nice.

These shoes look great in brown or black. Each has its own vibe, and either would look great with your most worn-out jeans or nicer casual pants. At $275 per pair, they’re a bit pricier than a lot of the Timberland line, but if its in your budget, they really are beautiful.

Timberland Earthkeepers ‘Rugged Originals Pull On’ Boots

Here’s another boot from the Earthkeepers ‘Rugged Originals’ line. This time, it’s a simple, pull-on boot. While boots like these are certainly stylish enough for guys who like make fashion a priority, they’re also great for guys who just want their boots to serve and protect, without a lot of frills or trendy features.

This particular style is available with dark brown or red brown, oiled leather uppers. And again, both would look good with jeans or casual pants. I think the lighter version shows the variation of the leather a bit more than the darker brown, but it’s also got more of a western feel to it. So, if you’re looking for a boot that has more of an urban feel, go darker. Otherwise, stick with the red-brown.

‘City Adventure Slip-Ons’ – Timberland Shoes for Men

Oh, how I love nice Venetian driving mocs — especially when they have suede or nubuck uppers, like these sweet slip-on shoes from Timberland. And, even more so, when like these loafers, they’re discounted to more than 40% off their original price. Of course, that also means that they might be sold out by the time you are reading this, but as of this writing, there is a good selection available in U.S. men’s sizes 7-13, medium (D) and wide (EE) widths.

Available with either the tan-gray uppers you see here, or with deep blue. I prefer the lighter shade, because I think it’s a bit less predictable. But, only slightly, and you really couldn’t go wrong with either. Especially when they’re marked at less than $55 per pair.

There’s no doubt that these would work well with chinos or cords, but my favorite way for casual loafers like these to be worn is with a pair of relaxed or loose-fit jeans.

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