How to Wear Timberland Boots for Ladies

Written by Kalee Hewlett | Edited by Madeleine Flamiano

Last Updated: May 28, 2022 References

Have some classic Timberland boots lying around? That's lucky, because Timberland boots can totally up-level your style. Here, we'll tell you how to put together casual, chic, and sporty looks with classic Timberland boots. Jump right in to get the most mileage out of your Timberland boots and dress up with them all year-round.

This article is based on an interview with our celebrity stylist & confidence coach, Kalee Hewlett. Check out the full interview here.

1

A geo pattern sweater and jeans

Pair this with Timberlands to look cozy and cabin-ready. Classic yellow Timberlands and simple blue jeans go with any geometrical print, so choose a sweater with any pattern or color. Sling on a crossbody bag and you're good to go.^{[1]
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- For a preppy look, slip your sweater over a striped button-down shirt.
- When it's really bright out, pop on wide-rimmed sunglasses.
- If it's extra chilly, try on a jacket in a neutral color.

2

A puffy jacket, casual top, and statement jeans

Give off outdoorsy vibes with Timberlands and warm outerwear. First, choose your favorite pair of statement jeans—for example, they can be bright red, camo print, or leather. Then, choose a sweater or tee in a neutral shade like beige or grey. Finally, slip on a puffy jacket that complements the color scheme you put together.^{[2]
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- For an aviator look, choose a puffy jacket with a fur hoodie.
- Leave your hair down and skip any products for a super casual vibe.
- Tuck sunglasses into your top's collar to show you're ready for anything.
- Wear a gray puffy jacket with gray Timbs and any jeans for an ultra modern look.

3

A bomber jacket and boyfriend jeans

Come across as military-chic with Timberlands and a slick coat. For a unisex or tomboyish look, slip on boyfriend jeans. Then, keep it simple with a white tee—it can be fitted or oversized. Finally, slide into your fave military jacket. Green, black, or tan coats are all awesome choices.^{[3]
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- Iron patches onto your military jacket to add even more personality.
- To add a bit of sexiness, go for a white crop top.
- Roll up your jacket's sleeves and show off a watch or beaded bracelet.

4

A camel coat, neutral top, and blue jeans

A brown-toned jacket is perfectly color-coordinated with Timberlands. In order to make your camel coat stand out, choose a tee or sweater in a neutral, cool tone like beige, cream, or grey. Wear dark or light blue jeans to complement the brown shades in your outfit.^{[4]
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- Try delicate gold jewelry like stud earrings or dainty necklaces.
- If you want to include sunglasses, try brands with gold rims.
- Add sophistication by wearing a turtleneck sweater and styling a high ponytail.
- Whip up some autumnal whimsy and pair your camel coat with orange Timbs.

5

A thermal long sleeve shirt and slim fit jeans

Make yellow Timberlands pop with a dark top. Go super casual understated with any dark top—like black or navy blue—and slim fit jeans that aren't distressed. For extra color, add a flannel button-down shirt over your long sleeve shirt. Keep your makeup earthy and simple.^{[5]
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- Tie your flannel shirt around your waist for another way to accessorize.
- For a grunge look, choose a dark blue, dark green, or dark gray flannel.
- For a preppy vibe, try a purple, pink, or light blue flannel.
- If you want an airport-ready outfit, sling your carry-on bag over yourself.
- Round-rimmed sunglasses go best with this outfit.
- In the summer, swag leggings or jeans for a pair of shorts.

6

A cute top and a pair of ripped jeans

Add edginess to fresh and clean Timberlands with distressed pants. Timberlands are super versatile and go with any ripped jeans, so just choose your fave pair! Then, decide on your top—it can be fitted and sexy or oversized and casual. Depending on the weather, you can slip on a color-coordinated jacket or just skip a coat.^{[6]
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- For a chic look, try white ripped jeans, a white top, and a black coat.
- For an urban style, experiment with destroyed denim jeans and a hoodie.
- For an everyday outfit, pair destroyed jeans with a sports cap and a tank top.
- For a punk vibe, try acid wash ripped jeans, sneakers, and a leather coat.
- Mix femininity with edginess and go for a crop top, hoop earrings, and an updo.
- A bright pair of Timbs—like green, blue, or mixed-media—would add a pop of color to this edgy 'fit.

7

A rock band tee and your fave jeans

Show you're down for a concert or musical festival with this look. Go for jeans in any color or style—they can be white, black, or blue as well as ripped or undistressed. Choose a fitted or oversized rock band tee that reps your favorite musicians.^{[7]
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- For an outdoor music festival, put on beaded earrings and earthy makeup.
- For a soft, indie vibe, pair a boho band tee with ripped jeans and beige Timbs.
- For an indoor concert, do a dark smokey eye and style your hair in messy waves.
- For a punk or goth band, have fun with chokers, gauge earrings, and black Timbs.^{[8]
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- Wear purple or burgundy Timbs to make a black rock band tee and black leggings pop.

8

A wool jacket, sweater, and leggings

Take on chilly weather with this chic layered ensemble. First, slip into a dark pair of leggings. Then, choose your favorite sweater in any color you like. For a super cozy look, go for a cable-knit. If you want to be more understated, try a simple thermal sweater in a bold color. Then, sling on a purse or your favorite fashion backpack.^{[9]
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- For extra elegance, match your leggings to your wool coat.
- Color-coordinate classic Timberlands with a brown monogram backpack.
- In the fall, pair an autumnal sweater and coat with brown Timbs and wool socks.
- When it’s extra cold, try a pair of fur-trimmed Timbs and throw on an oversized scarf.
- Stick to basic makeup to sell the understated sophistication of this look.

9

A blouse and leggings

Elevate Timberlands with these dressy, sophisticated pieces. Start with a blouse that will match with your Timberlands. For example, if you've got classic Timberlands, try neutral or warm silk blouses or experiment with animal print. Then, slide on some color-coordinated leggings. Complete your outfit with a fitted hip-length jacket.^{[10]
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- For fun flair, try on black leggings and a black jacket with zipper accents.
- Add some silliness and whimsy with your favorite beanie.
- Get wild and expressive with your manicure—any color will work!
- If you’d like to add even more sexiness for a date night, try heeled Timbs.

10

A sweater, camel midi skirt, and quilted jacket

These staples give Timberlands a preppy, semi-formal feel. If you want to give off a cute librarian vibe, pair a camel midi skirt with a sweater in any color. Go for a slouchy cable-knit sweater or a form-fitting long sleeve shirt. Then, round out the look with a quilted jacket that's color-coordinated with your sweater. Sling on a neutral purse or backpack for extra charm.^{[11]
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- A pastel sweater looks sweet and innocent with a camel skirt.
- A black or white form-fitting sweater lends a fun allure to the outfit.
- A light blue sweater and a dark blue jacket are great for spring.
- A light pink sweater and a salmon pink jacket are ideal for a chilly summer.
- A light orange sweater and a burnt orange jacket are a great call for fall.
- A white sweater and a brown jacket are a chic combo for winter.

11

A muscle tee and joggers

Timberlands give activewear an urban chic flair. For camo joggers, try a muscle tee in a solid color like white, black, or gray. If you want to try on joggers in a solid color, go for a graphic muscle tee to add some flair to your outfit. Finish your look with a sporty hairstyle, like a ponytail or a braid.^{[12]
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- For a flirty touch, wear a dark bra under a transparent white muscle tee.
- For something a little more form-fitting, swap a muscle tee for a tight crop top.
- Add some old Hollywood glam to black joggers with a pair of red Timbs.
- Experiment with graphic earrings to add whimsy to your activewear.
- Match your Timbs’ shoelaces to your tee or joggers for a fresh and unique look.
- Give IG influencer vibes with beige joggers, a white crop top, a puffy jacket, and white Timbs.

12

A black mini dress and denim jacket

A snug dress and a cute jacket make Timberlands super alluring. Wiggle into a black bandage dress or slide into a black cami dress. Pair black socks with your Timberlands to make sure you're color-coordinated with your dress. Put on your favorite denim jacket. Then, add a thin black choker to complete your girly ensemble.^{[13]
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- Focus on a dark lip so you can make your outfit pop.
- For a date night, go for a fitted denim jacket.
- A white floral sundress and pink Timbs look ultra feminine together.
- If you're having fun outdoors, try an acid wash denim jacket.
- A white mini dress goes great with brown Timberlands and lace socks.

13

A knitted dress

This pretty piece adds femininity to a pair of Timberlands. Go for a midi, mini, or two-piece knitted dress. Choose shades that are ideal for your pair of Timberlands—for example, if you have classic yellow Timberlands, try black, cream, brown, or burnt orange knitted dresses. Finish your look with layered metallic jewelry, a dark matte makeup palette, and a fresh manicure.^{[14]
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- A neutral manicure really helps your knitted dress stand out.
- The combo of a knitted dress and boots give off a "girl boss" look.
- Use fashion sunglasses as a headband for a cool, femme fatale vibe.
- If you want effortless elegance, try a black midi knitted dress with a black purse.
- For a preppy style, go for a plaid, argyle, or checkered two-piece knitted set.

14

A t-shirt dress

Timberlands and a breezy t-shirt dress make a sweet combo. Timberland boots will go with any casual dress, so pop on any t-shirt dress you feel confident in. Your t-shirt dress can be fitted or oversized as well as bold or striped. Balance out your down-to-earth garment with heavier makeup and your favorite jewelry.^{[15]
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- Pair a sports jersey dress with a chunky necklace and hoop earrings.
- A scarf headband goes great with Timberlands and a striped shirt dress.
- For effortless cool, try a black t-shirt dress without any accessories.

Expert Q&A

Question

What kind of jeans look good with Timberland boots?

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

Boyfriend jeans and skinny jeans are both great options when you're styling Timberland boots. Boyfriend jeans are more laid-back and casual, while skinny jeans can look more dressed up.