Can You Wear Timberlands With Skinny Jeans? (Or Any Jeans?)

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Yes You Can Wear Timberlands With Skinny Jeans

So you want to wear a pair of casual Timberland boots, but you’re worried about looking a little too rugged. If that’s the case, you don’t have to fear. Corduroy jeans are a great option for creating a preppy look that won’t overpower the aesthetic of the Timberlands, while skinnies or slim straight-leg jeans will add more edge to your outfit.

A large part of what makes Timberland boots so great is that they are the perfect clash of ruggedness and style. A pair of slim jeans gives this boot look a polished finish, while a boot-cut jean balances its tough aesthetic.

You can pair your favorite skinny jeans with your favorite pair of Timberlands. With the right size, your skin-tight jeans will hug your legs to show off your shoes.

Do I Tuck My Jeans Into My Timberlands?

You can wear your jeans both ways but your Timberlands boots look so good they deserved to be shown off and the best way to show them off is by tucking your jeans in.

Tuck your skinny jeans into your boots for that cool, laid-back style. No one will be able to stop themselves from asking you where you got them.

The best way to wear jeans with Timberland boots is to wear them tucked into your footwear. You can wear any jeans such as bootcut jeans or flared jeans, but be sure to roll the cuffs upwards and secure them in place with a single stud. Jeans with a slight mid-rise will fit well with the Timberland boots.

A lot of people tuck their pants into boots all wrong. They put them over the tongue or even worse, over the top. The proper way to tuck your pants into your boots is to tuck them under the tongue (the part with the laces) and then place the laces over the top. This will give you that classic look that you are probably going for.

The Timberland designs feature a range of fits, from classic straight to slim flare, chinos, and skinny jeans. Regardless of the style of pants you choose, they should be rolled around the top of the shoe and tucked into the tongue. This will ensure a tailored appearance while leaving enough room for shoes to breathe.

Can You Wear Timberlands Women’s Boots With Skinny Jeans?

Conventional wisdom says skinny jeans are supposed to be worn with flats. But when paired with Nellie boots, your favorite denim legwear will show it can rock out in any season. Stretch denim is ideal for the fall because it won’t constrict your thighs the way your pants would in winter.

The Nellie is a classic ankle boot that looks great with skinny jeans or leggings. Thanks to an authentic crisscross leather piece, they’re casual, cool, and comfortable all at once.

And instead of clomping around in ton-of-bulk chunky boots, go for the lightweight Nellie ankle boot. After all, it’s always fun to break out of your shell. Let’s see what people have to say about wearing these boots with skinny jeans…


Timberland Women’s Nellie Double Waterproof Ankle Boot


Timberland Women's Nellie Double Waterproof Ankle Boot,Black,5 M US

Click image to view on Amazon


When looking for boots to wear with skinny jeans, I wanted ones that would be comfortable but that I could also run around in. The Nellie boot is both aesthetically pleasing and my go-to for everyday activities.

  • I chose the Nellie boots because I figured the ankle boot would be easier to pull on, and I liked how they looked with skinny jeans.
  • Looks great with skinny jeans, relaxed baggy pants, and bootcut pants
  • I love them, especially the look with leggings and skinny jeans.
  • Great boots love them! Comfortable and looks good with skinny jeans.
  • The Nellie boot by Timberland is the perfect boot not only for great hikes but also for everyday life. I love how comfortable and rugged they are!
  • Wear them with your favorite pair of skinny jeans, and your outfit will be ready for anything.


What about with all jeans?

  • I’m a senior and these aren’t only comfortable, they’re cute with jeans or with a denim skirt and leggings.
  • They are cute with jeans.
  • They keep my feet dry and warm, and they look great with both jeans & sweatpants.
  • I bought these for cold, wet days ahead and also for how they look with jeans.
  • Very comfortable and look good with a pair of jeans.
  • I wear them with jeans and even Nike tights. They are my favorite boots.
  • They are both comfy and stylish with jeans, leggings, or skirts.
  • I wore them to work with a pair of jeans, and a pink short blazer on casual Friday and received a lot of compliments on the look.

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Can You Wear Timberlands Men’s Boots With Skinny Jeans?

Timberland Men’s Earthkeepers Rugged Hiking Shoe I’ve been wearing the same pair of boots every day to work for years. Why? Not because I’m a manchild who tosses his mother’s vacuum cleaner compared to a Roomba every Saturday, but because I have a very comfortable pair of Timberland Earthkeepers that requires no breaking in period. They go great with skinny jeans and look excellent with just about any pair of jeans.

They’re versatile as well and go with jeans as well as khakis. They look excellent with just about any pair of jeans, from tight-fitting dark denim to a more casual light wash.

I wanted to make them compliment my outfit. For example, I like skinny jeans and tanks during the summer. So when I grab my converse all stars I can grab a pair of my Tims and put on a nice button-down shirt with the sleeves rolled up and add another layer of clothing underneath it to stay cool in the hot weather…


Timberland Men’s Earthkeepers Rugged 6″ Boot



Timberland Men's Earthkeepers Rugged Hiking Shoe, Red Brown, 7

Click image to view on Amazon


These boots give you outstanding support on rugged trails, while still providing a clean look with slim jeans.

  • They also look amazing and everyone has something nice to say about them. (they go great with skinny jeans)


What about with all jeans?

  • A great pair of boots for casual wear, they look excellent with just about any pair of jeans.
  • I received tons of compliments every time I wear it with khakis, jeans, shorts, and any casual clothes at the office or job site.
  • After 2 years of use and abuse, I can clean them up, wear them with a nice pair of jeans, and still get compliments on them!
  • They have a special anti-fatigue sole that feels very pleasant on your feet. Plus, they look badass with jeans.
  • Looks great on Jean’s primary reason for me to buy them.
  • I bought these to dress up with my jeans and to do a lot of NY city walking.
  • They look amazing with a pair of jeans.
  • They’re versatile as well and go with jeans, chinos, and I even wear them to work in the hospital where I’m on my feet all day.

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In summary, Timberland’s are the best boots you will ever own. Not only are they incredibly comfortable, but they are so durable you can wear them year after year. It is best to tuck your pants into your Timberland’s boots if you don’t want any scrunching or sagging.

If you’re hip to wearing Timberland boots with the right outfit, the best look for them would be a nice pair of slim jeans, a jacket, and a nice shirt. Don’t shy away from experimenting with other items as long as your street punk vibe is intact. Wearing Timberlands with jeans is probably one of the most classic combinations that you can choose.

You may also be interested in… Timberland Is A Good Brand and What Is Calvin Klein Jeans? (Classic, Versatile, Modern, Urban, Iconic)