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1Tuck your pants into your Timbs for a streamlined outfit.
2Cuff your pants for a trendy, tapered vibe.
3Slip into sweats or leggings for an extra-comfortable ensemble.
4Leave your Timbs partly unlaced to show your street style.
5Lace your Timbs tightly for a preppy look.
6Prepare for cooler weather with baggy jeans and a jacket.
7Play up the rugged side of Timberlands with cargo pants.
8Cozy up for winter with a puffy parka.
9Slip on a stylish jacket to give your outfit a classy touch.
10Pair a sweater and jeans for a studious outfit.
11Give your outfit some edge with a rugged jacket.
12Create a bold, streetwise outfit with monochromatic clothes.
13Try a double-denim look for a clean, matching outfit.
14Wear a dress with Timberlands for an edgy look.
15Stay casual in a crop top and jeans.
16Stay cool with a button-down shirt and shorts.
17Embrace the 90s with a pair of camo pants.
18Choose classic yellow Timberlands for an iconic streetwise look.
19Pick black Timberlands for a sleek look.
20Add an element of surprise with brightly-colored Timberlands.
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Co-authored byKalee Hewlettand Janice Tieperman
Last Updated: January 10, 2024References
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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.
1
Tuck your pants into your Timbs for a streamlined outfit.
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2
Cuff your pants for a trendy, tapered vibe.
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3
Slip into sweats or leggings for an extra-comfortable ensemble.
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4
Leave your Timbs partly unlaced to show your street style.
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Leave the laces out of the top 2 eyelets. Then, loosen up the laces and either leave them untied or tie them loosely.[4]
- 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, Celebrity 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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6
Prepare for cooler weather with baggy jeans and a jacket.
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7
Play up the rugged side of Timberlands with cargo pants.
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8
Cozy up for winter with a puffy parka.
Download Article
9
Slip on a stylish jacket to give your outfit a classy touch.
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10
Pair a sweater and jeans for a studious outfit.
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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.[10]
- 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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12
Create a bold, streetwise outfit with monochromatic clothes.
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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.[12]
- 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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14
Wear a dress with Timberlands for an edgy look.
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15
Stay casual in a crop top and jeans.
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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.[14]
- 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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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.[15]
- 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.
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18
Choose classic yellow Timberlands for an iconic streetwise look.
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19
Pick black Timberlands for a sleek look.
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20
Add an element of surprise with brightly-colored Timberlands.
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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.[19]
- 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
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Question
What kind of pants go best with timberlands if I'm a girl?
Kalee Hewlett
Image ConsultantKalee 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.
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Question
What top works best with timberlands and jeans if I'm a girl?
Kalee Hewlett
Image ConsultantKalee 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.
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Thank you for your feedback.
As a small thank you, we’d like to offer you a $30 gift card (valid at GoNift.com). Use it to try out great new products and services nationwide without paying full price—wine, food delivery, clothing and more. Enjoy!Claim Your GiftIf 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 wikiHowYesNo
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![20 Simple Ways to Style Timberland Boots - wikiHow (48) 20 Simple Ways to Style Timberland Boots - wikiHow (48)](https://i0.wp.com/www.wikihow.com/images/thumb/4/45/Kalee_Hewitt1.jpeg/-crop-100-100-78px-Kalee_Hewitt1.jpeg)
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Kalee Hewlett
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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.’ This article has been viewed 102,146 times.
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Co-authors: 7
Updated: January 10, 2024
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Categories: Boots
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