How to Dress Up with Timberland Boots for Ladies

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The classic Timberland boots are a must-have for all the fashionable ladies out there like me.

In fact, I believe all women deserve a pair of Timberland boots.


Because they are super stylish and trendy.

In this article, I will show you the best outfit ideas you can follow when wearing your Timberland boots.

How to Dress Up with Timberland Boots for Ladies

Timberland boots are super iconic and classy.

Yes, they indeed look funny and too masculine at first.

But when you pair them with the right outfit, you would look super lovely with it.

Trust me, I have doubted my Timberland boots before.

But when I got to wear them with different outfits, I realized how super fashionable and versatile they are.

Check out this list I made to see which outfit suits your taste best.

Timberlands with shorts

One of my most famous go-to outfits is the Timberland boots and shorts combo.

This will be the perfect match if you want to look slimmer and sexier with your Timberland boots.

Denim shorts are the best type of outfit that can go with a pair of Timberlands when going out for casual settings.

It’s also super easy to style and they can go with almost all types of tops.

You can also wear this combo with a plaid cardigan or a leather jacket to appear more chic and stylish.

Timberlands with dress

For the ladies who want to look feminine with their Timberland boots, opt for a dress.

Again, many women might have second thoughts when wearing their Timberland boots.

Some of them think they are too chunky and rugged.

But wearing it together with a dress would give it a softer and more delicate touch.

The rugged look of your Timberland boots can also give a striking contrast when worn together with a dress.

For the fall or winter season, midi-length dresses topped with a denim jacket or cardigan would look perfect with your Timberlands.

It will also help in keeping you warm from head to foot.

Planning to wear your Timberland boots with a dress during the summer season?

I recommend maxi and mini dresses.

This type of dress would give you a very feminine and breezy look.

Which can show off your most delicate and aesthetic features.

Accessorizing this with your sunglasses and summer hat would also be the perfect fit.

Timberlands with leggings

Now for the ladies who kept on asking about how to wear Timberlands with leggings, here’s a nice tip for you.

Timberlands and leggings are one of the easiest combinations to wear.

Actually, these pairs can be worn in both formal and casual setups.

If you’re just out to get some coffee or bread, you can top our leggings and Timberlands with a simple oversized shirt.

This will give you a super stylish and comfortable look.

But, if you want to go to work with your leggings on and a pair of Timberlands, opt for a long-sleeved button-down shirt.

You can also wear a blazer over them to complete your professional and smart appearance.

Timberlands with skinny jeans

Want to look comfortable and stylish at the same time?

Why not try wearing your Timberlands with jeans, specifically your skinny jeans.

This is another combo that can be styled with any top, depending on the look you are trying to achieve.

And just like your leggings, this wardrobe choice is perfect for both casual and formal events.

You can tuck in a nice long-sleeved polo shirt in your skinny jeans and wear them with your Timberland boots.

This can give you a very smart and more put-together kind of look.

And if you want to appear sexier and elegant, wear a crop top or a tank top with your skinny jeans and Timberland boots.

You can accessorize this with some light jewelry to complete your whole outfit.


Another chic and stylish combo is the Timberlands and skirt pair.

Although not all skirts would look good with your Timberlands so beware when choosing what skirt to wear.

You can go for a mini skirt with a Timberlands outfit and top it with a hanging shirt or a crop top.

This can give you a very feminine and sexy look.

Maxi skirts and Timberland boots can also be a pair although you have to be very careful on the top you choose to complete this outfit.

It’s perfect for the fall or the winter season to keep yourself warm and still look very stylish.

Timberlands with Joggers

For me, many women tend to look down on joggers a lot.

But in reality, joggers can also be super stylish, especially when worn together with classic Timberland boots.

If you want to look sporty and comfortable, you can pair your Timberland boots with a pair of joggers.

Styling this with a tank top or a fitted shirt would be the best choice if you want to look stylish.

You can accessorize this outfit with a necklace that has two layers or your favorite watch and bracelets.

Oversized shirts

Join the trend by wearing your favorite Timberland boots with an oversized shirt.

Since Timberland boots are big, wearing them with an oversized shirt would make a really great complement together.

This combo can also give you an edgy and somewhat rugged kind of look.

You can wear these two together when going out with friends or hanging around the park.

It’s super comfortable and can easily make some heads turn towards your direction.


Just like your oversized shirts, your Timberland boots can also give a very striking appearance with hoodies.

This type of wardrobe choice is perfect for any season.

But they are most especially trendy during winter.

Hoodies are comfortable and can create a very stylish look together with your Timberlands.

You can wear your hoodie alone with your Timberland boots.

This will give you a sexy look and give your outfit some character.

You can also wear hoodies with jeans together with your Timberland boots.

This will create a more casual and classy look for you.