Timberland Boots with Jacket

Timberland boots go well with a variety of jackets, allowing men to add their favorite modern jacket or classic coat to their outfit without hesitation. From bombers to denim to leather jackets, you can wear Timberlands with several jacket styles, but the trick is to combine your outwear appropriately with the rest of your look. You can try a chino chore jacket to continue drawing on the workwear aesthetic. To dress the latest trends, go classic with a field jacket or keep it simple with a bomber jacket. The type of jacket you pick can accentuate the aesthetic you are cultivating with your outfit, so choose outerwear that can be worn with pieces that you already own.

Timberland Boots with Coat

Well-suited for cold winter months, Timberland boots go well with all types of coats. Your Timberlands with jeans and a fishtail parka is a classic street casual look for the winter. Try an overcoat in black or camel hair to elevate your cold-weather outfits and stand out from the crowd.

Timberland Boots with Sweater

Sweaters with Timberland boots can look refined if executed correctly. Choose the right sweater for your look: clean merino wool sweaters are more refined while fisherman’s sweaters are cozy and traditional. Combine your sweater with black jeans, Timberlands, and other winter accessories like scarves and beanies for a simple, clean look.

Timberland Boots with A T-Shirt

Because they are so versatile, Timberland boots can be worn with simple T-shirts. To rock a minimalist aesthetic, try your Timberland boots with a clean T-shirt that fits you well and simple jeans. Try a high-collared or scallop-edged tee with simple accessories for a fashionable take on this look.

Timberlands with Shorts

If you like streetwear or want to dress a casual outfit in the summer, you can consider pairing Timberlands with shorts. Timbs and shorts are an uncommon combination, but some guys can pull off the look with style. Whether you want to match cargo shorts, athletic shorts, or baggy shorts, Timberland boots can work with different types of shorts. We just recommend that you tread carefully since the outfit can be hit or miss, and it all depends on the color and style combo of the Timbs and pair of shorts.