20 Simple Ways To Style Timberland Boots - WikiHow

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How to Style Timberland Boots Download Article Explore this Article IN THIS ARTICLE 1 Tuck your pants into your Timbs for a streamlined outfit. 2 Cuff your pants for a trendy, tapered vibe. 3 Slip into sweats or leggings for an extra-comfortable ensemble. 4 Leave your Timbs partly unlaced to show your street style. 5 Lace your Timbs tightly for a preppy look. 6 Prepare for cooler weather with baggy jeans and a jacket. 7 Play up the rugged side of Timberlands with cargo pants. 8 Cozy up for winter with a puffy parka. 9 Slip on a stylish jacket to give your outfit a classy touch. 10 Pair a sweater and jeans for a studious outfit. 11 Give your outfit some edge with a rugged jacket. 12 Create a bold, streetwise outfit with monochromatic clothes. 13 Try a double-denim look for a clean, matching outfit. 14 Wear a dress with Timberlands for an edgy look. 15 Stay casual in a crop top and jeans. 16 Stay cool with a button-down shirt and shorts. 17 Embrace the 90s with a pair of camo pants. 18 Choose classic yellow Timberlands for an iconic streetwise look. 19 Pick black Timberlands for a sleek look. 20 Add an element of surprise with brightly-colored Timberlands. + Show 17 more... - Show less... Other Sections Expert Q&A Video Related Articles References Co-authored by Kalee Hewlett and Janice Tieperman

Last Updated: June 3, 2025 References

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This article was co-authored by Kalee Hewlett and by wikiHow staff writer, Janice Tieperman. Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’ There are 8 references cited in this article, which can be found at the bottom of the page. This article has been viewed 131,270 times.

Originally meant for construction jobs and manual labor, Timberland boots have transformed into a versatile and iconic fashion statement over the past few decades. From flannels and jackets to dresses and peacoats, these sturdy boots work well with a variety of different ensembles. If you’re in need of a little inspiration, take a peek at this list to help you get started.

The Best Ways to Wear Timberland Boots

• Tuck slim-leg pants, baggy jeans, or joggers into Timberland boots.
• Roll up the cuff of your pants to just above the top of your boots.
• Wear sweatpants or leggings with Timberlands for a casual, comfy look.

Steps

1

Tuck your pants into your Timbs for a streamlined outfit.

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1. Pick out a pair of pants with a slim fit. This pants style helps balance out the bulkiness of your Timberlands.
   • For a winter ensemble, pull a pair of socks into the bottoms of your pants. Then, tuck both your socks and pants into your Timbs.
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2

Cuff your pants for a trendy, tapered vibe.

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1. Roll up your pants so they stop just above the tongue of your boot. Make the cuff around 2 inches (5.1 cm) wide and roll it 3 times to get a hem that falls just above the boot.
   • This basic cuff works best with a slim-cut pair of pants.

3

Slip into sweats or leggings for an extra-comfortable ensemble.

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1. Timbs and comfy bottoms are great for lounging around. Top the outfit off with a flannel to complete this cozy look.
   • Elevate the look with an interesting sweater or bag to keep it more fashion-forward.
   • Keep your look casual with a hoodie.
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4

Leave your Timbs partly unlaced to show your street style.

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1. Leave the laces out of the top 2 eyelets. Then, loosen up the laces and either leave them untied or tie them loosely.[1]
   • To avoid your Timberlands falling off of your feet, lace the bottom eyelets more tightly and leave the laces loose around the ankles.
   • You can also try re-lacing the shoes while skipping every other eyelet. Leave the top eyelet undone.
   June Ambrose, Stylist

   Timberlands have become a staple in hip hop fashion by embracing the boots' rugged utilitarianism with an urban edge. Play with exaggerated tongues, loose laces, and rolled cuffs to make them your own. Pair with baggy jeans or joggers tucked in for an authentic street vibe. Timbs demand attention, so keep the rest of your look minimal.

5

Lace your Timbs tightly for a preppy look.

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1. Timbs don’t always have to be casual! You can make them look more dressed-up by lacing them tightly around your ankles. This will give you a clean, fitted look.[2]
   • Try changing up how you lace your Timbs based on what you're wearing.
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6

Prepare for cooler weather with baggy jeans and a jacket.

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1. Slip into a plain tee as the base of your outfit. Then, keep things loose with a pair of baggy jeans, along with a sturdy, rugged jacket. Slide into your Timbs to finish off this casual look.[3]
   • Create a cool contrast with tan Timbs and dark jeans.
   • A bomber or jean jacket works well with this look.

7

Play up the rugged side of Timberlands with cargo pants.

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1. Timberlands were originally created to be work boots. To lean into this casual style, try pairing your Timbs with cargo pants or even overalls. Then, finish off the outfit with a white tee.[4]
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8

Cozy up for winter with a puffy parka.

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1. Try a long puffy coat with skinny jeans to play with different proportions. Add a touch of luxe by looking for a coat with fur around the hood.
   • Try a pea-coat for a more preppy look.

9

Slip on a stylish jacket to give your outfit a classy touch.

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1. Start off your look with a varsity-style jacket. Then, balance out the jacket with your favorite pair of blue jeans. Slip on your Timbs, and you’re to head outside![5]
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10

Pair a sweater and jeans for a studious outfit.

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1. Sweaters add a cozy, elegant touch that contrasts with your Timbs. Slip on your favorite sweater, along with a pair of slim-fitting jeans. If it’s especially cold out, bundle up in a cozy hat and scarf before braving the elements.[6]
   • You can tuck your jeans into your boots for a more polished outfit, or leave them untucked.

11

Give your outfit some edge with a rugged jacket.

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1. Slip into a slim-cut bomber jacket to keep your outfit on the streetwear side. To make your look even edgier, wear a black leather jacket instead.
   • Burgundy, khaki, and olive green bomber jackets all pair well with Timbs.
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12

Create a bold, streetwise outfit with monochromatic clothes.

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1. Pick out a matching top and pair of pants. To really go the extra mile, slip on a matching coat or cardigan to create a streamlined outfit. Finish off your eye-catching ensemble with a matching pair of Timbs.[7]
   • You might pair a white top with a white pair of jeans, along with a white cardigan and a white pair of Timbs.

13

Try a double-denim look for a clean, matching outfit.

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1. Wear a dark wash, slim-cut pair of jeans with a fitted chambray shirt. To make the look extra rugged, pick out a distressed pair of jeans.[8]
   • Triple the denim by adding a jean jacket on top.
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14

Wear a dress with Timberlands for an edgy look.

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1. Contrast the rugged look of these work boots with a flirty dress. Go for a looser-fitting dress for a casual look, or a short dress for a sexier outfit.
   • To make this outfit cozier, go for a flannel or sweater dress and tights.

15

Stay casual in a crop top and jeans.

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1. Slip into a pair of slim, form-fitting jeans. Then, show off a little skin by wearing a crop top over top. To complete your look, slide on a cardigan, and put on your favorite pair of Timbs.[9]
   • This type of outfit works great with neutral tones. For instance, you might mix a white crop top and jeans with a dark cardigan, along with a tan pair of Timberlands.
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16

Stay cool with a button-down shirt and shorts.

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1. A pair of sturdy Timbs are an excellent companion on summer days. Pick out a pair of comfortable shorts, along with a button-down shirt or another breezy top. Finish things off with a pair of ankle socks, along with a pair of Timbs.[10]
   • Just about any top works well with a summer outfit—staying cool is what’s most important.

17

Embrace the 90s with a pair of camo pants.

Download Article

1. Slip into a pair of slim, comfortable camo pants. Contrast the pattern with a plain white tee, along with a denim jacket. Finish off your streetwise outfit with your favorite pair of Timbs.[11]
   • Slim pants help add a modern twist to this nostalgic look.
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18

Choose classic yellow Timberlands for an iconic streetwise look.

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1. The yellow, high-top Timbs are classics for a reason. Throw them on with any outfit and you'll instantly add an element of cool.[12]
   • Yellow Timberlands are instantly recognizable and can be dressed up or down. When in doubt, go with the originals.

19

Pick black Timberlands for a sleek look.

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1. These Timbs are great for a monochromatic look. Black Timbs can add either a touch of sophistication or grunge to your look, depending on what you pair them with.[13]
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20

Add an element of surprise with brightly-colored Timberlands.

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1. Timbs also come in colors like red, blue, and pink. Try finishing an all-black outfit off with bright Timberlands, or go for a fun, colorful look from head to toe.[14]
   • Timberlands also make boots in limited-edition colors and patterns, so keep an eye out if you want to add an unusual style to your closet.

Expert Q&A

Search Add New Question

• Question What kind of pants go best with timberlands if I'm a girl? Kalee Hewlett Image Consultant Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’ Kalee Hewlett Image Consultant Expert Answer Timberland boots look great with boyfriend jeans if you want to go for a more laid back look. They're also great with skinny jeans or leggings and some thick cable-knit socks. Thanks! We're glad this was helpful. Thank you for your feedback. If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow Yes No Not Helpful 2 Helpful 5
• Question What top works best with timberlands and jeans if I'm a girl? Kalee Hewlett Image Consultant Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’ Kalee Hewlett Image Consultant Expert Answer A classic denim shirt or a lumberjack flannel are great options. You can also go for the classic white T. Thanks! We're glad this was helpful. Thank you for your feedback. If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow Yes No Not Helpful 3 Helpful 2

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References

1. ↑ https://www.yournextshoes.com/wear-timberland-boots-girls/
2. ↑ https://www.yournextshoes.com/wear-timberland-boots-girls/
3. ↑ https://medium.com/@lifetailored/how-to-wear-timberland-boots-mens-style-guide-65f75f61aa94
4. ↑ https://www.yournextshoes.com/wear-timberland-boots-girls/
5. ↑ https://m.youtube.com/watch?v=DWvDQoocJrQ&t=2m32s
6. ↑ https://medium.com/@lifetailored/how-to-wear-timberland-boots-mens-style-guide-65f75f61aa94
7. ↑ https://www.instyle.com/celebrity/celebrities-love-timberland-boots?slide=997ec842-3de8-422d-a2c4-1e1cb717f8bd#997ec842-3de8-422d-a2c4-1e1cb717f8bd
8. ↑ https://www.thetrendspotter.net/what-to-wear-with-timberland-boots/
9. ↑ https://www.instyle.com/celebrity/celebrities-love-timberland-boots?slide=b3ce51cb-07c6-446c-a1ef-81216d670486#b3ce51cb-07c6-446c-a1ef-81216d670486

More References (5)

10. ↑ https://medium.com/@lifetailored/how-to-wear-timberland-boots-mens-style-guide-65f75f61aa94
11. ↑ https://m.youtube.com/watch?v=DWvDQoocJrQ&t=1m21s
12. ↑ https://stylecaster.com/how-to-wear-timberlands-like-a-fashion-girl/
13. ↑ https://www.yournextshoes.com/wear-timberland-boots-girls/
14. ↑ https://www.yournextshoes.com/wear-timberland-boots-girls/

About This Article

Co-authored by: Kalee Hewlett Image Consultant This article was co-authored by Kalee Hewlett and by wikiHow staff writer, Janice Tieperman. Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’ This article has been viewed 131,270 times. 10 votes - 90% Co-authors: 7 Updated: June 3, 2025 Views: 131,270 Categories: Boots In other languages Portuguese German Japanese

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Yes No Advertisement Cookies make wikiHow better. By continuing to use our site, you agree to our cookie policy. Co-authored by: Kalee Hewlett Image Consultant Co-authors: 7 Updated: June 3, 2025 Views: 131,270 90% of readers found this article helpful. 10 votes - 90% Click a star to add your vote

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