Men’s Style Guide: What to Wear with Timberlands

man wearing tan timberland boots in front of a wall
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Last Updated on December 29, 2022

There is something timeless and understated about a man wearing a pair of Timberland boots. Cool, calm, and collected— these iconic shoes have been around since 1952 as the all-around “problem solving” boot.

While they’re often interpreted as a working man’s boot—in construction sites, workshops, or the outdoors, Timbs has evolved into a 21st century fashion staple, specifically within streetwear.

The brand Timberland has collaborated with icons such as Supreme, Comme des Garcons, and Off-White. Celebrities have begun wearing and creating looks with Timbs inspired by cargo prints, rugged aesthetic, and even including a blazer.

Want to know how to wear Timberland boots with outfits without looking like a lumberjack?

Here’s the lowdown:


With T-shirts

The easiest way to pull off a pair of Timbs is by styling them with a tee shirt. Avoid graphic tees with designs or texts, and instead opt for solid-colored tops in neutral shades. Consider black, white, navy, nude, maroon, or olive green.

These will set a serious tone for your outfit and make the boots look more structured and put together, casual and informal. Black tee shirts are always a safe bet since they look great on everyone. Pair them with baggy denim pants, and tuck them into the Timbs.

Make sure your Timbs are tied together neatly for this look, since tee shirts are very casual garments. Small details such as the way the shoes are laced can make a big difference in the overall appearance of the outfit. Accessorize simply and neatly, with a classic watch or a thin chain around your neck. Any color of Timbs will do.

Read: Timberland 6-inch Basic vs. Premium: I Reveal Which to Choose

With loose casual tops

Loose top are another simple yet chic way to style Timberland boots. Depending on the kind of top you choose, you can dress up or dress down the boots.

We recommend a casual top, such as one made from knit or any kind of soft material. Roll up the sleeves if it is long sleeved, and unbutton the top section. Leave the top untucked from whatever you decide on wearing as a bottom. We suggest a pair of dark wash, loose and baggy jeans. Tuck the hems of the jeans into a pair of Timbs.

For this particular look, we envision that the boots are more loosely tied, with every other eyelet pulling a lace through. Accessorize the look with a casual Panama style hat. This look is highly reminiscent of streetstyle, and is a classic look that will never go out of style.

Read: 17 Men’s Outfits that Defined the 90s



Perhaps the most iconic pairing are blue jeans with Timberland boots. From the workspace, to streetstyle, to runway shows—these always find their way back to each other as the perfect combination of comfort, practicality, and style.

There are no limits as to what jeans can or cannot be paired with Timbs. They all look equally as good.

From darker washes, to lighter variations, to dyed jeans, skinny jeans, wide legged jeans—the options are endless. For an edgy style idea, choose a pair of jeans that seem like they belong at a construction site—along with the boots.

Consider a pair of light wash, ripped jeans that are structured yet slightly loose and oversized. Loosely tuck them into your favorite Timbs. Style with a grey tee shirt and hoodie for a casual look that can be worn seasonally. Accessorize with gold or silver jewelry.

Read: Undeniable Proof that Men’s 90s Jeans are Here to Stay

With Shorts

Timberland boots and shorts are not a combination that is favorable to everyone. This pairing is very particular, and not an overall favorite since it can be aesthetically unpleasing to men with shorter legs. If you are tall, go for it if you wish.

Timbs are heavy boots meant to withstand harsh weather conditions, and can be hot for the spring and summer. Some men might even find them uncomfortable. Therefore, pairing them with heavy pants such as blue jeans can make wearing them unbearable. This is why some men opt instead for shorts.

Consider a pair of knee length denim shorts. Style simply, with a solid-colored top, and socks that show above the boot. Tie up your Timbs neatly. This style idea is perfect for those days when it’s too hot to wear pants, but you still want to wear your Timberland boots.

With Joggers

While many men prefer opting for skinny pants when wearing their Timberland boots, we suggest considering joggers as well. Joggers and Timbs make a great combination for many different reasons. They are the ultimate comfortable duo—they make for an ideal traveling outfit.

Choose a pair of joggers that fit you accordingly, and go for neutral shades such as white, black, or gray. Next, pair them with a tee shirt to go with the casual vibe. If the weather is colder, combine with a snug bomber jacket or leather jacket. This choice depends on your style preference.

Style with a baseball cap and sunglasses for a cool, laid-back appearance. Tuck the hem of the joggers into the Timberland boots, and tie the boots up tightly. The joggers are informal enough without the added informality of untied shoelaces. This look is ideal for the airport, or for running quick errands in the city.

It’s informal, yet equally as stylish as the other alternatives.

With khakis

If your style is defined as classy and formal, khakis are the way to go when wearing your Timbs. They provide an element of refinement like no other, and will definitely let others know you are not necessarily a construction worker—but a man of good taste.

Choose a pair of khakis that are tapered and fitted rather than loose and oversized. Make sure the waist is your exact size and accessorize with a belt if need be. Style with a black crew neck sweater and leave it untucked above the trousers.

Formally tuck the hems of the pants into the boots, and make sure to tie the laces neatly to go hand in hand with the formal aspect of the outfit.

Complete this khaki and Timbs outfit with a stylish puffer coat draped on top, in a neutral yet cool shade such as olive green. Choose Timbs in the tan shade or olive variations.

Read: 90s Men’s Sweaters: Back to Winter Past

By Color


Black Timberland boots are a cool and edgy alternative to the iconic yellow models. They are perfect to create a uniformed look and avoid the connotations that usually accompany a pair of classic Timbs.

You can style them in many different ways, from jeans, to joggers, and even with loose tops and coats.

We suggest creating a look that is based on comfortable fashion, and creating a careless aspect with rips and destroyed hems. Choose a pair of unconventional jeans, featuring multiple holes, rips, and pieces of fabric sewn over.

Top with a chunky knit sweater that is also ripped and slightly destroyed. Style with a cool bomber jacket on top to complete the look. Accessorize with gold jewelry and a beanie if need be.

Another alternative and the easiest way to style black Timbs when in a rush is to simply pair them with a fully black outfit, starting from a pair of ripped black jeans.


Timberland’s classic yellow boots are a viable option for all men, and can be paired with anything. If you are thinking of purchasing a pair of Timbs and this is your first time, we highly recommend going for these rather than the other variations. These are the most classic and iconic models, no matter your age or personal style.

For a casual winter streetstyle outfit, begin with a pair of yellow Timbs and leave the laces slightly undone. Make sure they are widely tied, and tuck the ends inside without displaying them. Pair with a pair of black skinny jeans, but make sure they are widely ripped over the knee.

Style with a long, slightly oversized white tee shirt. Throw a closed neck sweatshirt on top if the weather gets chilly.

Accessorize with cool accessorize such as black sunglasses and a leather jacket. Any kind of craft jewelry will also look great with this outfit.


Tan Timberland boots are slightly more formal than the classic yellow versions. They have a more serious tone, and are often preferred for more formal occasions, even though they are still considered streetwear garments.

Build an outfit based on a neutral color palette, one that matched the tan shade of your Timbs. Think of something easy, formal, yet very chic. Begin with a pair of gray toned denim pants, but make sure they are fitted rather than loose. Tuck the hems into the boots, and make sure the laces of the Timbs are tied to perfection.

Throw on an oversized white tee shirt on top of the jeans, and complete the look with a tan notch collar coat. Leave the coat unbuttoned.

This look is ideal for a dinner date, night out on the town, casual get togethers, or a day of running errands when you wish to look a little bit extra put together.

By Boot Structure


There are two different structures of Timberland boots; low, and high. The low variations are less common, as they are not as iconic as the 6-inch-high structure. However, the low versions are equally as stylish.

To style the low versions, consider leaving the laces slightly loose and undone. Attempt to make the tops wide and comfortable, and tuck any kind of pants into them. Low Timbs look best when paired with trousers but are the best choice when considering wearing Timberland boots with shorts.

For an easy style idea, begin with a pair of skinny black trousers.

Shop for a pair of low top black Timbs. Style with a white tee, navy puffer jacket, and beige scarf loosely draped over your neck. Dark, neutral, and classy. This look is very reminiscent of the city aesthetic and streetstyle, and can be worn all year round.


The high version of the Timberland boot is the most classic and iconic. These are the best in terms of practicality, and overall style.

You can wear these with anything, but steer clear of chino pants or shorts—try avoiding anything that will show too much leg, as for those cases we recommend going for the low versions of Timbs.

These high versions are 6 inches and wrap around your ankles very comfortably. Ideal for the workplace or streetstyle, pair them with any kind of solid-colored trousers. Always tuck the hems into the boots.

The high versions are available in all the different shade variations offered by Timberland, but we recommend sticking to classic yellow if you want to create that effortless, Timberland-esque look.

By Season


While it may seem strange to wear boots during the spring and summer, Timberland boots can be worn throughout the whole year. You just have to style them correctly so that they are not uncomfortable in any way, especially within hot weather. Style with cut out jeans and a button up top.


Timberland boots can become your summer staple shoe. Ideal for hiking or any sort of outdoor activities, they are highly practical. Style them simply during the summer, with comfortable t-shirt and loose trousers. Shorts are also okay with Timberland boots during the summer, especially exercise shorts.


For the fall, Timberland boots are a staple for every man. Warm and comfortable, these will keep your feet snug and stylish. Wear with a statement jacket and dark wash jeans all fall long. Consider incorporating plaid shirts as well, as they look great with Timbs. You can layer garments for extra warmth as well.

Read: How to Wear a Denim Jacket with Style (Men’s Outfit Guide)


Timberland boots are the perfect show for the winter, no matter where you live. In places where it snows, these boots are perfect as they are famously waterproof and ideal for trudging through the snow. We suggest combining them with a classic puffer jacket in a metallic shade, and always layering underneath.

How to Lace Timberlands

Timbs feature sturdy laces that are meant to tie around the show tightly. When styling Timbs in a more casual setting:

  1. Loosen the laces
  2. …but not too loosely (stay comfortable)
  3. Wear them wide

A tighter, laced boot looks sharper, cleaner, and will make you seem more put together. This is appropriate for a more formal occasion or the workspace for safety reasons. For a laidback, effortless vibe, wear the laces loose.

You can even try skipping every other eyelet for edge. Lace your Timberland suede boots based on your personal preference and particular styles.

Read Next: 10 Boots Like Timberlands (But are Definitely From Other Brands) – Men’s & Women’s Edition