Timberlands have become one of the most popular boots in the world. Rugged and stylish, Timberland boots are a wardrobe staple for construction workers and fashionable men alike. While these men’s boots were originally designed to be functional and tough, this iconic style has transcended the workplace and can now be found in streetwear and smart casual fashion. As the iconic brand has grown, the company has expanded its selection of colors beyond the traditional yellow boot. Today, you can find Timberlands in black, white, red, brown, blue, grey, and green. Timbs also come in different boot styles, such as Chukka, Chelsea, dress, hiking, winter, and sneaker boots.
Great for both casual and trendy outfits, it’s important to know how to wear Timberlands and the kinds of clothes that look cool with them. To inspire your style, we’ve compiled the ultimate guide on what to wear with Timberland boots. If you want to rock the perfect ensemble, see all the different ways you can style your outfits with Timberlands!
- 1 Timberland Boots Outfit Ideas
- 2 Timberland Boot Styles
- 3 Timberland Boots Size Guide
- 4 How To Lace Timberland Boots
- 5 Are Timberlands Waterproof?
- 6 What To Wear with Timberlands
Timberland Boots Outfit Ideas
Timberland boots are casual and cool, but are versatile enough to suit several aesthetics and match different types of outfits. Whether you want to wear jeans and a t-shirt, joggers with a loose sweater, or shorts with a relaxed button-down, these iconic men’s boots will look great on you!
Timberland Boots with Jeans
Timberlands and jeans are a natural fit, making this outfit a popular choice for men. While jeans are the go-to option when wearing Timberland boots, there are many ways to style this combination. For starters, denim comes in different colors, allowing guys to choose between light and dark wash blue, black and grey jeans. You can mix and match styles by pairing black Timberland boots with light blue jeans or the traditional tan Timbs with black jeans to create contrast in your look.
Further, you may prefer Timbs with slim-fitted skinny jeans or feel more comfortable in loose baggy jeans. For the latest trending fashion, you’ll want to wear Timberlands with cuffed slim or straight-cut jeans. This combination allows you the freedom to dress your top how you want, so finish the outfit with a shirt, sweater, flannel button-down, bomber jacket, or oversized coat.
The beauty of dressing boots and jeans together is you can achieve a casual or smart casual look with ease by adding upscale clothes to the ensemble, thereby expanding where and how often you can use these wardrobe pieces.
Timberland Boots with Denim
Timberland boots and denim tops create a workwear style that continues to be a classic look for guys. Whether you choose a denim shirt or jacket for your outfit, the rugged look of the material pairs will with Timbs. To avoid a sloppy look, try pairing dark denim with a chambray shirt or other lighter variations of denim. Combine your Timberlands with jeans for a double denim outfit or swap in stylish chino pants or cargo pants to create additional variations of the style.
Timberland Boots with Blazer
For a smart casual style you can wear out, Timberland boots can be dressed up with a blazer. It is important to pay attention to the details with this look, as it can look disjointed if done incorrectly. An easy go-to combination might be dark jeans and a thick textured blazer for a great smart-casual ensemble for colder days. On nice summer days, a t-shirt with jeans and Timbs is all you need for a polished handsome look.
Timberland Boots with Jacket
Timberland boots go well with a variety of jackets, allowing men to add their favorite modern jacket or classic coat to their outfit without hesitation. From bombers to denim to leather jackets, you can wear Timberlands with several jacket styles, but the trick is to combine your outwear appropriately with the rest of your look. You can try a chino chore jacket to continue drawing on the workwear aesthetic. To dress the latest trends, go classic with a field jacket or keep it simple with a bomber jacket. The type of jacket you pick can accentuate the aesthetic you are cultivating with your outfit, so choose outerwear that can be worn with pieces that you already own.
Timberland Boots with Coat
Well-suited for cold winter months, Timberland boots go well with all types of coats. Your Timberlands with jeans and a fishtail parka is a classic street casual look for the winter. Try an overcoat in black or camel hair to elevate your cold-weather outfits and stand out from the crowd.
Timberland Boots with Sweater
Sweaters with Timberland boots can look refined if executed correctly. Choose the right sweater for your look: clean merino wool sweaters are more refined while fisherman’s sweaters are cozy and traditional. Combine your sweater with black jeans, Timberlands, and other winter accessories like scarves and beanies for a simple, clean look.
Timberland Boots with A T-Shirt
Because they are so versatile, Timberland boots can be worn with simple T-shirts. To rock a minimalist aesthetic, try your Timberland boots with a clean T-shirt that fits you well and simple jeans. Try a high-collared or scallop-edged tee with simple accessories for a fashionable take on this look.
Timberlands with Shorts
If you like streetwear or want to dress a casual outfit in the summer, you can consider pairing Timberlands with shorts. Timbs and shorts are an uncommon combination, but some guys can pull off the look with style. Whether you want to match cargo shorts, athletic shorts, or baggy shorts, Timberland boots can work with different types of shorts. We just recommend that you tread carefully since the outfit can be hit or miss, and it all depends on the color and style combo of the Timbs and pair of shorts.
Timberlands with Sweatpants
Wearing sweatpants and joggers with Timberlands can be a great way to walk around town in comfort. While most sweats and jogger pants are extremely casual, new variations from high-end designers and streetwear brands have given these staple pieces an elevated makeover. Guys can choose thin, skinny joggers in the summer or thick, loose sweatpants in the winter. For a cohesive look, you may even want to buy a tracksuit consisting of a matching long-sleeved jacket and long pants. If you style your outfit properly, you can exude a cool confidence with sweatpants and Timbs.
Timberland Boot Styles
Today, Timberland has diversified their catalog from when they were just a work boot company. Though their iconic yellow boot is the most popular style, Timberland has created a large selection of boots, from chukkas to hiking boots. With so many options, there is a Timberland boot for every man.
6” and Above Boots
These boots are for guys who prefer the classic Timberlands and want the protection and style afforded by its quality build and iconic status. These six-inch Timberland boots are common on the street as well job sites for construction workers who need a heavy-duty work boot. Perfect for keeping your feet protected from gravel or insulated from inclement weather, these tall boots are available in a wide variety of colors and styles to match any outfit.
Timberland’s winter boots are ideal for those who still would like to keep their feet warm and dry without sacrificing style. Winter boots offer the most protection from the elements, with waterproofing and insulation to keep the feeling in your toes even in the coldest weather. Unless stated otherwise, you can safely assume that your Timberlands are waterproof and can be worn in the rain and cold weather months of the year.
Chukkas are a staple for any modern man’s wardrobe, and Timberland chukka boots are made with the same excellent workmanship, quality, and style as the traditional footwear that made this brand popular. Timberland chukkas are great to pair with chinos or slim-cut denim jeans, but the style is versatile enough to work with all types of outfits. Featuring a slimmer profile and lighter feel while still being waterproof, Timberland chukka boots provide style and function.
For men who are adventurous and like the wild outdoors, Timberland makes a high-quality selection of hiking boots. As with their other footwear lines, Timberland hiking boots are well-made and comfortable, resulting in a shoe that is both stylish and utilitarian. The brand will keep you looking fresh on the summit or the street while protecting your feet on all terrains.
Timberland’s sneaker boots combine the practical, sturdy nature of their boots with a modern aesthetic. These boots elevate the traditional sneaker and provide a unique look for casual streetwear. This versatile shoe can be worn everywhere your sneakers would.
In addition to their standard tall boot, Timberland offers a selection of mid-height boots. These include shorter utility boots, hiking shoes, and sneakers. If you prefer a shoe that hit at or just above your ankle, these are the shoes for you.
Perfect for sleek looks that are easy to get on and off, side-zip boots from Timberland come in a wide array of styles. They have utility boots for your on-duty uniform or sleek leather offerings for your evening motorcycle ride.
Slip-on boots allow you to waste no time getting out the door. The sleek, laceless look can complement many outfits. Of course, these boots offer the same durability as other Timberland offerings.
Timberland Boots Size Guide
Timberland offers a convenient and accurate shoe sizing chart to help you determine the right size to buy Timberland boots in. Generally, Timberlands run big so we recommend buying boots that are a half size smaller than your sneaker size. For instance, if your shoe size is 10, then order Timbs in a size 9.5.
How To Lace Timberland Boots
Timberland boots are often worn with the laces relatively loose across the tongue of the boot. To achieve this look when lacing Timbs, we recommend unlacing the boots when you buy them and re-lacing them to create the ideal look for your style. Many men lace their Timberlands without using the final two eyelets and tying the ends of the laces off so that they don’t slip.
Some guys also like to lace their Timbs by skipping every other eyelet for a loose fit, while others use every eyelet for a tight style that won’t slip off your feet. How you lace up your boots ultimately depends on whether you’re wearing your boots for style or function. Of course, you are free to experiment to find the best look for your boots.
Are Timberlands Waterproof?
Yes, Timberlands are waterproof and each pair has been rigorously tested to protect your feet in rain and snow. Because most Timberland boots are made from nubuck leather, your foot will stay dry but the leather material will still stain your footwear. To maintain and care for your Timbs, we recommend a leather treatment in the form of a suede protectant and waterproofing product that will ensure the longevity and look of your boots.
What To Wear with Timberlands
- Choose casual outfits to complement your boots. Timberlands are not meant to be used as dress shoes.
- Complete your outfit with simple stylish pieces such as jeans, t-shirts, sweaters, bomber or leather jackets, and relaxed button-down shirts.
- Wear your Timberlands during the winter with jeans, a shirt layered with a sweater, and an overcoat or puffer jacket.
- Pair your Timberlands with jeans, chinos, joggers, sweatpants, or jumpsuits.
- For a smart casual look, style your Timberland boots with a blazer and dark denim jeans.
- Try different styles such as chukka, Chelsea, sneaker, and hiking boots to find the types that best match your look and fashion.