How to Wear Timberland Boots with Skinny Jeans

How to Wear Timberland Boots with Skinny Jeans -
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Timberland is one of the biggest and most popular boot brands out there. You will see the boots on construction sites, city streets, fashion runways, and in magazines. Needless to say, the brand is timeless and has become a staple streetwear item.

However, even though Timberland boots are popular, some men struggle to find a fashionable and “manly” way to wear these shoes with skinny jeans. Do you simply wear them over the cuffs of the jeans? Some men find that this makes their legs appear excessively skinny, which is not ideal.

Next, we will be looking at a few ways in which you can take wearing your Timbs with skinny jeans to a whole new level.

Get Creative With Lacing Up Your Timbs

There are many fancy and creative ways that you can lace up your boots. If you want to spice up your look, undo your shoes and pull the shoelaces from them.

You could simply go for the old “loose-boot look”. To achieve this, lace your shoes up as normal, but be sure to skip every second hole. This means that you will end up not using the last eyelet, which will give your boots a more open feel and look.

Another popular technique is the “hidden bar lace”. Feed the shoelace through the bottom eyelet, but be sure that the tips of the lace end up on the inside of the boot. You must then pull one end of the shoelace through the next open eyelet so that it is on the outside. Run this lace through to the opposite hole and back to the inside of the shoe. Repeat this method until you reach the top of your boots.

There are many websites that you can follow in order to find alternative lacing techniques, such as Ian’s Shoelace Site, which offers instructions to 62 different lacing methods.

Lace Your Timbs Loosely

By now, most people should know that Timberland boots look much better when they’re not tied up tightly around your ankle. The loose boots give the appearance that you didn’t put much effort into your look - which is good.

This doesn’t mean that you should be falling out of your boots with every step that you take. Instead, tie your laces loosely so that the shoe is tighter towards the bottom and more open towards the top. This will also contradict the tight look of your jeans, which will bring more balance to your outfit.

Cuff Your Skinny Jeans

If you are planning on wearing your Timberland boots during the summer, this is a must. Cuffed jeans give your outfit a casual and cool twist, which is perfect for the hot summertime.

Many guys simply roll their skinny jeans so that they lie just above the shoe. However, this can give you an abnormal silhouette. The better option is the pin roll.

The first step is to unroll your skinny jeans. You will then have to fold the inside of the pant inseam on top of itself - this will leave you with two layers on top of each other. Lastly, roll the cuff like you normally do.

You could also try the “deep cuff”. This look is old school and becoming more and more popular. However, this technique may not be the best for you if you are relatively short.

There are also websites that you can visit to find other ways to cuff your skinny jeans, such as Business Insider, which gives you a step-by-step guide.

Stack Your Skinny Jeans

This is possibly the best way to wear your jeans with Timberland boots, as stacking your pants will reduce the tight look of the skinny jeans.

A couple of years ago, stacked jeans were seen as unfashionable and lazy. However, they have become more popular in recent years as the “effortless” look is starting to dominate fashion.

All you have to do to get the stacked look is pull your pant legs up a bit so that they don’t reach your ankles. The extra material will crease and leave you looking as good as the most fashionable men out there.

Wear Ripped Skinny Jeans

I’m sure you have noticed that the casual look is trendy right now, and nothing says “effortless” like a pair of ripped skinny jeans.

These pants are everywhere and for a good reason - they often add that little bit extra to your outfit. You also have the option of buying three different types of ripped jeans: small-cut jeans, sequel-cut jeans, or huge-cut jeans.

Small-cut jeans have slight rips that aren’t too noticeable. Sequel-cut pants are slightly more ripped up. These are the most popular types of ripped skinny jeans out there. Huge-cut jeans have rips that show off your leg and are often a little too much for most people.

Ripped skinny jeans are a favorite to pair with Timberland boots. Fashion icons, such as Kanye West and Drake, are often seen at events wearing these two items of clothing.

Pair Your Skinny Jeans With a Baggy Shirt

Timberland boots are bulky. The main reason that skinny jeans don’t look right with them is because they are tight-fitting. This is why wearing a baggy or an oversized shirt can be the perfect solution - it can balance out the two looks. You could also try wearing a big jacket over your skirt, which will have the same effect.


There are many ways for you to pair Timberland boots with skinny jeans. Try various creative ways of lacing up your boots. You could also leave your laces loose so that the shoes don’t sit so tightly on your feet. Stacked and cuffed skinny jeans are becoming more and more popular, especially with bulky shoes like Timbs.

Wear a pair of ripped skinny jeans with your boots, as this will give you an effortless and carefree appearance. Lastly, you could try pairing your skinny jeans with a baggy shirt or jacket.

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