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How To Wear Timberland Boots

I love writing about all kinds of clothes, shoes, and accessories. Very rarely will I write about a brand because I’m the type who only thinks about looks and quality. But right now there are two brands that I don’t really see as brands. Instead, I see them as genres. They are the Converse sneakers and the Timberland boots. Note that I am not even capitalizing the brand names here, just as I am not capitalizing white sneakers and ankle boots. They’re so classic that they just stick to the same design here and there with a little twist. In this blog post, I want to put together some of my favorite ways to style Timberland boots.

Wear it with a black trench coat and skinny jeans

black trench coat leggings timerland boots
Get a pair of similar wooden boots here
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I’ll start the list with a dark and stylish all-black look. Just wear a slim-fitting black sweater with a black trench coat and black skinny jeans. The Timberland boots are the only product that is not black. They just stand out and spice up the outfit.

Wear it with a long sweater, ripped jeans and a black leather jacket

black leather jacket green sweater Timberland boots
Get a similar black leather jacket here
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Boots are just fantastic when it comes to tough looks. Wear the long green sweater with ripped jeans and a black leather jacket. The Timberland boots go very well with the sweater and make the parts look well balanced.

Wear it with black skinny jeans and a gray bomber jacket

Bomber Jacket Black Jeans Timberland Boots Outfit
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Get similar camel boots here
For a casual fall outfit, you can wear a white t-shirt with a gray bomber jacket and black skinny jeans. Complete the stylish outfit with the iconic Timberland boots.

Long white t-shirt, black sweater and leather jacket

long white t-shirt leather jacket Timberland boots
Get a similar black sweater here
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For a sleek look with some layering tricks, you can try wearing a long white t-shirt and black slim fit sweater and black leather jacket over it. For the floor, combine the Timberland boots with black skinny jeans.

Wear it with black leggings and a long fleece coat

long fleece black coat timberland boots
Get similar wooden lace-up boots here
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If you are looking for a feminine and beautiful winter outfit that will keep you as warm as it looks good, you may have found the idea you need in this outfit. For the top, wear a red sweater with a long black fleece coat. Combine them with black leggings and the boots. The good news is that this outfit is surprisingly easy to take off for all body types.

Black and red plaid flannel shirt & shirt Jeans

Timerland boot with a plaid flannel shirt
Get a similar plaid boyfriend shirt here
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As a casual country low-key outfit, you can wear a black and red checked flannel shirt and tuck it into your jeans. The Timberland boots really add character to this simple outfit. By the way, you might want to check out our other blog post on flannel shirt outfit ideas.

Wear it with a plaid boyfriend shirt and denim shorts

Timerland plaid flannel shirt jean shorts
Get similar waterproof boots here
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For a spring-like look, you can try wearing the Timberland boots with a black vest top and denim shorts topped with a plaid boyfriend shirt.

Wear it with black and white leggings and a leather jacket

black and white leggings leather jacket boots
Get similar black and white striped leggings here
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This outfit is sure to be the most creative and artistic outfit on the list. It is the combination of the black and white striped leggings and the Timberland boots that make the outfit so unique. Pair them with a white blouse, black leather jacket and scarf. Every piece of this outfit just goes perfectly together and it just looks stunning.

Wear with a long white trench coat

white long trench coat black leggings boots
Get a similar quilted leather shoulder bag here
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For a striking look with contrasting colors, wear the entire black blouse and skinny black jeans. Combine them with a long white trench coat and the Timberland boots to complete this gorgeous winter outfit.

Wear it with a white sweater and black trench coat

black trench coat white sweater Timerland
Get a similar black wool coat here
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Here is another adorable winter outfit. Just wear a white sweater with black skinny jeans, Timberland boots, a black trench coat and a black beanie.

Denim jacket & ripped black jeans

Denim jacket ripped black denim boots
Get a similar light blue denim jacket here
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For a casual, simple and stylish look that is especially suitable for spring and autumn, you can simply wear a gray t-shirt, a denim jacket and black, ripped skinny jeans with your boots.

Blue trench coat & brown scarf

blue trench coat green scarf woodland
Get a similar chiffon scarf here
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This outfit is a great demonstration of how to wear brown and blue together. Wear a white top with blue jeans and a light blue trench coat. Wear a brown scarf that goes perfectly with the boots.

Wear it with a colorful faux fur jacket

colorful faux fur jacket
Get a similar gray felt hat here
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This outfit is only interesting because of the funky jacket. Start with the simple white t-shirt and cuffed jeans combo. Then pair them with a color-block faux fur jacket and a gray fleece felt hat. Of course, don’t forget the forest boots.

White shirt, long trench coat and ripped jeans

Timberland boots white shirt long trench coat
Get a similar trench coat here
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As a unisex outfit, you can wear a white shirt with ripped jeans. Combine the forest boots with a brown long trench coat.

Wear it with a white shirt, skinny jeans and a long trench coat


Get a casual jacket of a similar length here
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For a chic casual outfit that you can wear to work. Just wear a white button down shirt, black skinny jeans, a gray long trench coat and the Timberland boots.

Hope you enjoy the outfit ideas I just shared with you. The list has a single purpose: I want to show you some of my favorite Timberland boot outfit ideas so you can actually find some that actually work for you. Yes, I want to inspire you to trial and error and take your own outfit ideas to a whole new level. Learning how to style classic items like the Timberland boots is very useful as you can then fundamentally upgrade your daily outfit. At the beginning of the blog post I mentioned that I think the Converse sneakers are the other element that is so iconic. If you’re interested, you can also check out my blog post on Converse outfit ideas.

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