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Timberland Boots Style Guide: Outfit Tips & Inspiration

The truth is that any guy can look good sporting a pair of Timberland boots.

Think about it.

Few other brands of footwear have had their time to shine in literally every single style circle. 

Timberlands were made for hard-working everymen before they found their way into high-fashion. Their 90s and early-aughts association with hip hop stars make them a favorite among streetwear enthusiasts to this very day. Then, of course, there’s the outdoorsmen.

If you think that this iconic brand simply isn’t for you, allow me to try and change your mind. Whether you’re looking at the Timberland Premiums or their versatile White Ledges, this is how to wear Timberland boots in style.

How to Style Timberland Boots

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We’ll start with the most natural choice—styling Timbs with jeans.

Then we’ll go a more fashion-forward route with some style tips around black Timberlands, followed by an exploration on whether or not men can rock some pink boots (they can).

Styled with Jeans

timberland boots with ankle cuffed 1

There are two main ways to wear Timberland boots with jeans. You can go for a sleek modern look, or a traditional workwear look.

For a Modern Look, Wear Fitted or Tapered Jeans With Your Timbs

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Though their Original Yellow Boots came out in 1973 and were made for blue collar workers on the jobsite, Timberlands became a style icon by the late 80s. This was largely thanks to the rap scene and interest from fashion capitals like Milan, and so today, Timberlands are often worn in a sleekly casual way.

Timberland Premium 6-inch Waterproof Boot

The Timberland Premium 6-Inch Waterproof Boot is a handsome and iconic design and it’s built well. The quadruple stitching, Primaloft insulation, thick rubber heel, and padded leather collar are all designed to go the distance, whether for work or for style. The biggest drawback is the cemented sole construction, which simply isn’t as strong as a Goodyear welt.

Check Price Read Our Review

The first rule for styling your boots in a contemporary way is to choose fitted or tapered jeans. Depending on your personal preference or your body type, you might not be comfortable with jeans that are too close to the body all around. Tapered jeans are slightly loose around the bottom and thighs, but fit close to the ankles.

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This fit achieves two things: 

  • It shows off the tongue and the lacing, which is the most universally accepted way to wear Timberlands. 
  • It allows your Timbs to provide a strong base for the outfit’s overall silhouette.
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This is what I mean by a “strong base”.  

If you top off your jeans and boots with a fitted henley shirt or a basic crewneck, then the Timberlands become the statement piece of the outfit. The overall look is simple and made even more handsome since it’s capped off with strong masculine boots.

If you add a piece of outerwear, say a bomber jacket, a leather biker jacket, or even a peacoat, then the overall strength of the outfit is its balance There’s more bulk at the top and the bottom of the silhouette, and it’s reined in by the slim or tapered jeans. 

Pro tip: If you go the peacoat route, color-match it to your boots.

Basically, by pairing your robust Timberlands with tapered or fitted jeans, you set yourself up for success. Your style will usually work regardless of how the rest of the outfit pans out, at least silhouette-wise.

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Even when you’re wearing them in a modern and fashionable way, remember that Timberlands are still work boots, and thus pair well with textures and layers. 

We’ll get into the specifics regarding the lacing later, but if you choose to cuff your jeans, lace them up tighter then you would if you didn’t cuff them. Cuffing is a more deliberate and put-together way to wear jeans, so the Timbs should match that.

There’s no denying that baggy jeans have historically been paired with Timberlands. If you’re confident in pulling off this old school hip hop look, there are ways for us non-celebs to pull it off. We’ll get into that under the Outfit Ideas section below.

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As always, darker jeans are sleeker and more urban, while blue jeans will bring out the Americana and workwear side of your Timbs, which leads us to the second way to style them.

For a Traditional and Effortless Workwear Style, Go for Classic Fit Jeans

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Most of today’s fashion staples came about from practical needs. It’s always a winning choice for your outfit to hat-tip that staple’s original use because it feels authentic. For example, a dive watch will always look good with nautical stripes, a navy jacket, or boat shoes.

Classic-fit jeans of any color pair well with any model of Timberland boots. The combination of classic-fit blue jeans and Original Yellows are a timeless, casual, and masculine look. 

From flannels to denim jackets, you can top this approach off with your favorite textures and layers. Go for a quilted hunting vest a la the L.L.Bean Waxed Cotton Down Vest for a sophisticated outdoorsy look.

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And actually, you don’t always have to finish this aesthetic off with a hardcore workwear or outdoorsy look. As long as you achieve balance in textures and shapes, you can pull off a low-key but fashionable outfit.

How to Style Black Timberland Boots

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The first Timberland boots were yellow because they were made from durable nubuck. For the most part, sporting black Timbs is 100% a fashion choice, so you’ll want to follow a lot of the same advice previously mentioned for styling your boots in a modern way. That being you can’t go wrong with slim or tapered pants, then have fun with the rest of the silhouette.

Timberland Premium 6-inch Waterproof Boot in Black Nubuck
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Fortunately, on the color front, black really does go with everything. 

When you style them with casual clothes, there’s an inherent cool factor to it. For example, blue jeans with yellow Timbs and a henley shirt is a perfectly handsome and approachable combination. 

Change it up to black boots and dark jeans, and it shifts into a style-forward urban vibe. Throw a nice beige sweater over it, and you’re bordering on formal—at least upscale club-appropriate.

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Cuffing works excellently with black Timberland boots, especially if you’re wearing a nice pair of selvedge denim jeans.

If you go monochromatic, have fun with textures. You can try a slubbed cotton shirt with fitted modern cargo pants such as the SPECIALMAGIC Cargo Joggers, and a sherpa collar jacket like the Levi’s Trucker.

You can also style them similarly to how you’d style combat boots, if you like a tough biker style or a military casual tone.

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How to Style Men’s Pink Timberland Boots

There are many ways that men can and have worn pink to stylish effect. If you’re a trendy guy, you can have a lot of fun with rose-tinted Timberland boots, but there are subtle, more adult ways to wear them too.

Quick note: Timberland doesn’t make “men’s” shoes in pink hues, so you’ll have to head on over to the women’s section. When it comes to sizing, your equivalent in the ladies section will be one full number up. So if you’re a size 9, meaning your foot is around 10.6 inches, you’ll go for a women’s 10. 

My advice when it comes to wearing pink Timberlands is to use the color pink to accent the outfit, not headline it. You’ll also want to pick a lighter shade of pink.

Layering is Key

As mentioned, Timberlands go well with layers, and that’s the key to making this cheerful color look stylish and natural. You can wear an all neutral palette, grays and blacks for example, and top off the outfit with a light pink hat.

Another option is to wear a light pink shirt or sweater, then round it out with dark fitted selvedge jeans and a dark well-fitting jacket.  Feel free, in this case, to actually wear your pants over the tongue of the boots, to create more subtlety. You can also sport a flannel with subtle pink accents. 

Since pink is already such a playful color, you bring balance to the outfit with neutral colors and sophisticated textures.

Outfits With Timberland Boots

If you weren’t already inspired enough to try the style for yourself, check out these Timberland boots outfits for an extra nudge.

1. The Perfect Jeans Fit

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This guy is pulling off an on-trend boxy t-shirt because his jeans are tapering just as I previously described they should. He then takes it to the next level by having fun with the silhouette using that leather jacket.

2. Timbs with Ripped Jeans

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If you’re a ripped jeans kind of guy, balance out the tattered-chic look with neat cuffing and a good fit. In this case, the jeans are slim, but again, you can opt for tapered pants if you’re more comfortable with that. 

The basic top matches the overall slim shape of the outfit, while the texturing fits with the robust boots. 

3. Outdoor Chic

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By wearing perfectly tapered cargos and a basic top that compliments your body type, you can look perfectly handsome while bushwacking, without it looking out of place. 

Bonus points for practical yet stylish accessorizing (stainless steel sport watch and bandana scarf), and color-matching his trucker hat to his footwear—and his dog.

4. Classy and Casual

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Jake Gyllenhaal showcases the gold-standard of pulling off jeans with a classic fit here, proving you don’t always have to go the trendy slim route. 

By opting for darker jeans, darker boots, and a designer parka jacket (Canada Goose), this whole outfit is sophisticatedly and subtly glamorous, yet perfectly casual.

5. A Sleek But Casual Take on Black Timberlands

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Just as black Timberlands are, everything this fellow is wearing is essentially a rugged piece of workwear, but with a chic slant. 

The jeans are blue and ripped, but fitted, his utility shirt features a structured collar, good tailoring, and the sleeves are neatly folded.

6. Trendy and Youthful

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This look is basically a youthful take on the previous one, with the fitted ripped jeans and black boots. 

He uses his shirt as a pop of color, and instead properly buttoning it up, he leaves it open for a more casual t-shirt look. 

7. The Civilian Take on the Hip Hop Star Look

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Typically you don’t want your pants to stack too much, but in this case it’s part of the look. Moreover, a lot of the stacks are hiding behind the Timbs. 

The pants are baggy but not sloppy, and he cleans up the look with an athletic but neat piece of outerwear.

8. Wearing Timbs Like Combat Boots

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This is a good example of a hardcore biker look that might usually be finished off with some combat boots. You’ll notice that black Timberlands work just as well, while adding extra texture.

9. Borderline Formal

When I mentioned that pairing dark pants and black Timberlands with a beige sweater would up the outfit’s dressiness factor, this look by Drake is exactly what I meant.

Timberland Boots Laces Style 

More often than not, you’ll wear your laces slightly loose when wearing the Original Yellows. Obviously this shouldn’t be the case if you’re actually wearing them for the jobsite. 

If you’re wearing them for style and going for a streetwear tone, one tip is to wear the laces as loosely as you can, while ensuring they don’t slip off easily as you walk. You’ll do this by relacing the shoes and skipping every other eyelet.

For a more formal look, say with dark fitted cuffed jeans, just lace them up securely and cleanly, hiding the knot behind the lip for neatness.

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For hiking boot models like the White Ledges or Mt. Maddsens, you’ll lace them up securely even if you’re just wearing them for style. 

A Versatile Icon

Going for a modern and style-forward look? Start by pairing your Timbs with tapered or slim pants, then experiment from there. Remember that these boots go excellently with textures and layers.

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Giving the boots a nod to their roots, classic blue jeans are also a good base that you can take from workwear rugged to urban chic.

Don’t be scared to try unique colors, like light pink. You can pull it off with the right balance of neutral to bold shades.

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Now that you know how to style these iconic boots, go get yourself a pair.

Timberland Premium 6-inch Waterproof Boot

The Timberland Premium 6-Inch Waterproof Boot is a handsome and iconic design and it’s built well. The quadruple stitching, Primaloft insulation, thick rubber heel, and padded leather collar are all designed to go the distance, whether for work or for style. The biggest drawback is the cemented sole construction, which simply isn’t as strong as a Goodyear welt.

Check Price Read Our Review


What style of jeans should I wear with Timberland boots?

Wear tapered jeans or slim jeans for a modern look, or classic fit jeans for a rugged workwear look.

Can you wear Timberland boots with shorts?

For an outdoorsy look, pair Timberland hiking boots with slim cargo shorts that stop right below the knee or classic fit cargo shorts that stop right above the knee. For a more streetwear style, wear the Originals with athletic shorts, performance shorts, or dark denim shorts.

How do you style Timberlands in Summer?

In the summer, style Timberlands with shorts or light colored tapered cargo pants and a lightly-woven short-sleeve shirt, also in a light shade. Khaki, white, pale blues, and pale yellows will give your outfit that leisurely vibe.

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