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How to style your leather boots for a smart-casual look


How to style your leather boots for a smart-casual look

Black Timberland boots with pink trim

For years, leather boots have been a veritable wardrobe staple. Whether you’re soaking up the sun in the suburbs or delving into city life, leather boots are the ultimate secret to achieving a smart-casual look. As versatile as they are stylish, they are comfortable enough to withstand daily wear.

While leather boots in and of themselves appear simple in design, it can be challenging to style them for everyday wear. With a few key strategies in mind, you can master how to style leather boots for the better - and make your style seem totally effortless.

How to wear leather boots

When styling your preferred leather boot outfit, one must consider the level of formality to achieve, the type and colour of your chosen trousers, as well as the intensity of the environment where you’re walking. With the right leather boots by your side, you can hit the ground running.

As you consider how to wear women’s leather boots or men’s leather boots, rest assured there are a wide range of options available to you.

The first element to consider is the type of boots you’re wearing. From black leather boots to grey leather ankle boots, the styles of boots you can sport are virtually endless. Every style has unique benefits depending on your needs, with a huge range of colour options to consider as well.

For example, Chelsea boots offer classic elegance, which tends to elevate any outfit. As an added benefit, they are lace-free, so simple to slip-on and off throughout the day. If open lacing is more your preference, opt for brown leather boots with thin laces that are equally sleek yet functional.

Timberland brown leather boots

The right type of trousers, and their corresponding trouser length, are also critical to achieving the smart-casual look. Cropped jeans, skinny jeans and chinos tend to work best with men’s boots and women’s boots. In any case, avoid pairing knee-length leather boots with slacks and other dress pants.

Also, consider cuffing the hem of your pants to show the boot’s lip for added effect. Then, wear your new pair of Timberland boots with skinny jeans and a white t-shirt – then, you’ll be good to go. 

How to wear ankle boots

From pointed toe boots to desert boots, there are various ankle boot styles that you can consider to update your daily wardrobe. You may wear ankle boots, or booties, with jeans, pants, and even dresses and skirts in the warmer months. 

The key to wearing ankle boots well is to style them well. For those who are new to the ankle boot trend, start by dressing up your favourite pair of jeans for a night out. Cropped jeans match well with ankle boots, especially if you cuff the hems instead of tucking them into the lip of the boot. 

Then, layer them with a simple white t-shirt or blazer. If skinny jeans are more your style, you can still fold up the hem, but it’s not strictly necessary. 

Unlike jeans, ankle booties are a bit more challenging to wear with cropped pants or more formalwear. Consider pairing patterned or textured boots with high waisted silk pants and an oversized pullover. 

For those seeking to keep it classic (or finally spend that gift card you got at Christmastime), you can’t go wrong with a pair of Timberlands. Our signature collection of leather Chukka boots is specifically engineered to provide long-lasting comfort and a lifetime of wear. Equipped with a deconstructed finish, a pair of our relaxed men’s boots will rapidly become your go-to style for work and the weekend. 

Light brown Timberland shoes

How to wear Timberlands

The best way to wear Timberland boots is to lace them well, opt for tapered pants where possible, and remember to size down your work boots (they tend to run large.) While our work boots come in a range of colours and styles, we recommend keeping it classic if you’re new to the Timberland trend.

Timberland boots are as timeless as they are functional, and the Timberland 6 inch boot has become a style staple on both runways and worksites alike. As you browse your options, be sure to choose your colour wisely, lace them up loosely, and pair them with looser, baggier jeans for an on-trend fit.

For those who still aren’t quite sure where to start, you can’t go wrong with a pair of classic Yellow Timberland boots. This neutral hue not only goes with everything, but the Original Yellow Boot also continues to be a true icon and a canvas for American fashion, sports, and life itself.

For a bit of an edgier look, black Timberlands are guaranteed to hide dirt expertly and will go with pretty much any outfit (just ask “Hotline Bling” singer Drake, who never goes without his Black Timberland boots.)

Related: The Origins Of An Icon: The Timberland Original Yellow Boot

White Timberlands are always a bright idea in our book. Celebrities, including Rihanna and Jennifer Lopez, have been known to sport white Timberland lace-up boots for women paired with a simple white t-shirt and an oversized sweater.

Don’t forget to invest in a leather boot care kit for safekeeping. Treating your women’s, men’s, or kids leather boots regularly by brushing away dirt and applying cleaning products will help you protect your footwear and remove any stains that come with regular wear and tear.

Related: Timberland Boots: How To Clean, Protect, & Remove Stains

How to wear ankle boots with jeans

The best way to wear ankle boots with jeans is with cropped denim while tucking the hem of your trousers into the boots. Regular length skinny jeans can also work well with brown or black boots, in which case there’s no need to cuff or tuck your trousers into the lip of the boot.

A cropped pair of jeans will naturally not conflict with your boots because it hits above the edge of the shoe’s rim. Just be wary of showing too much skin between the bottom of your jeans and the top of your booties. Generally, your shoe should hit above the ankle bone to guarantee a flattering fit.

What are you waiting for? Shop Timberland today to nail the smart-casual look before you head out the door.