How to Wear Timberlands

by Aksana Nikolai ; Updated September 28, 2017

Timberland boots are a footwear choice of people who live in a climate characterized by cold temperatures and precipitation. If you are concerned about style, do not let the boots' practical appearance put you off. Regardless of gender, you can be stylish wearing Timberland boots.

Tuck your skinny jeans into the Timberlands, making sure that the tongue is over, as opposed to under, the jeans. If wearing flared jeans with Timberlands, make sure that the jeans are long enough to reach the sole of the boots.

Wear classic, flat soled Timberlands with leggings and a mini skirt. If you own the women’s style that resembles a heeled bootee, wear them with leggings and a sweater dress.

Pair knee-long sweat pants or men’s shorts with Timberlands and a fitted T-shirt. For a casual look, tie the boots loosely so that the tongue hangs out.

Fold the fabric portion of roll-top Timberlands down so that the pattern is visible. Alternatively, keep the fabric in its original position when your look requires high-top boots.


  • Balance the urban look of Timberland boots by wearing them in combination with preppy garments such as polo shirts and argyle sweaters.

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About the Author

Aksana Nikolai is a graduate of the New York Institute of Technology with a bachelor's degree in language studies and international affairs. Nikolai is currently working in online marketing and communications. She has been writing since 2008, specializing in made-for-Web content and maintaining her fashion and beauty blog.