'90s Fashion
Jan 1, 2023

10 Timberland-Boot Outfit Ideas We Love

by Melony Forcier

It's no secret that the Y2K resurgence has ruled the past few years, but simultaneously, fashion people are turning to the '90s for a bit of inspo too. The decade popularized some of our staple footwear brands, Vans, Dr. Martens, Converse, and of course, Timberland. Gen Z may not be as knowledgeable about the origins of this popular shoe brand, so to enlighten, Timberland started as a durable workboot but became known in fashion during the rise of the hip-hop and rap scene. Icons such as Notorious B.I.G. and Tupac, along with groups like Wu-Tang Clan, were often spotted in the shoes, and quickly they became synonymous with hip-hop and New York style.

The shoe remains just as relevant today, with celebrities including Jennifer Lopez, Rihanna, and Pharrell often sporting the boots. Most recently, the brand has taken on several collabs with brands ranging from Jimmy Choo to Kith, so you're sure to see the shoe everywhere in upcoming months. With durability and a waterproof exterior, we can't forget that they are the perfect boot for the winter season.

Perhaps you're looking to branch out from the classic 6" Work Boot style. Luckily, the brand has broadened its selection to include types from Chelsea boots to even heels; yes, you heard that right. So whether you're looking for the perfect pair of black ankle boots to pair with a lace slip dress or a fashionable shoe to sport on your next hike, you're sure to find a way to incorporate the shoe into your personal style.

If you're looking for a new way to style your Timbs, are considering purchasing your first pair, or just need outfit ideas with combat boots, we've put together 10 fashion-forward ways to wear the shoes, no matter your taste.

Timberland-boots-outfit-skirt

Photo:

@aude_julie

Who knew pairing Timberlands with a skirt could look so cool?

Timberland Cortina Valley Waterproof Hiking Boots

Cortina Valley Waterproof Hiking Boots

If you're looking for a more low-key approach to the Timberland shoe style, these combat-style boots are perfect. Plus, they are waterproof, making them snow and rain approved.

Edikted Alani Pleated Miniskirt

Alani Pleated Miniskirt

Don't try to resist a pleated mini skirt. You can't.

Everlane The Baseball Cap

The Baseball Cap

Everybody needs a plain black baseball cap in their wardrobe.

Timberland-boots-outfit-plaid

Photo:

Getty Images

Adding a statement jacket to a pair of Timberlands, denim, and a white tee can bring the simple look to the next level.

Timberland 6-Inch Premium Waterproof Boot

6-Inch Premium Waterproof Boot

Doesn't get more classic than this pair of Timberlands.

Triarchy Ms. Triarchy Cut Jeans

Ms. Triarchy Cut Jeans

These Triarchy jeans are super discounted right now, so grab them while you can.

Topshop Oversize T-Shirt

Oversize T-Shirt

Another staple. Must we say more?

timberland-boots-outfit-sweatshirt

Photo:

@timberland

This laidback monochrome moment is the perfect cozy weekend ensemble. Throw on your boots, and you're ready to go.

Timberland Work Boots

The ease of Amazon shipping makes these Timberland boots a no-brainer.

H&M Sweatshorts

You can never have too many pairs of sweatshorts.

H&M Oversized Hoodie

Oversized Hoodie

Or sweatshirts for that matter.

Asos Rains Long Waterproof Jacket

Rains Long Waterproof Jacket

A cute raincoat can be hard to find, but you can't go wrong with this minimalistic charcoal option.

Hue Women's Slouch Sock 3 Pair Pack

Women's Slouch Sock 3 Pair Pack

Hue socks are hands down my favorite.

timberland-boots-outfit-dress

Photo:

Getty Images

Try styling the boots with a lace slip dress, a statement jacket, tights, and a turtleneck for an unexpected wintertime ensemble.

Timberland Courmayeur Valley Boots

Courmayeur Valley Boots

For the wintertime, we love these shearling Timberland boots.

River Island Purple Faux Leather Quilted Bomber Jacket

Purple Faux Leather Quilted Bomber Jacket

Bomber jackets are going to make their way into 2023.

Splendid Fitted Turtleneck

Fitted Turtleneck

You can layer a black turtleneck under almost anything, and we are so thankful for that.

Commando Ultimate Opaque Control Top Tights

Ultimate Opaque Control Top Tights

These opaque tights have a matte finish.

timberland-boots-outfit-puffer

Photo:

Getty Images

Another statement coat look, but this time with a pink puffer. Timberlands truly are the quintessential winter boot.

Timberland Cortina Valley Chelsea Boots

Cortina Valley Chelsea Boots

If you are looking to stray away from the classic Timberland boot, try out a Chelsea boot style.

Mz Wallace Ruby Quilted Crossbody Bag

Ruby Quilted Crossbody Bag

You can never add too many shades of pink to an outfit. Right?

timberland-boots-outfit-vest

Photo:

@aude_julie

Tan Timberlands are made to be worn with this shade of green, especially in the fall.

Asos Design Nylon Onion Quilted Vest

Nylon Onion Quilted Vest

A vest to give your puffer a day off.

Abercrombie & Fitch Matching Set Quilted Sunday Sweatpants

Abercrombie & Fitch

Matching Set Quilted Sunday Sweatpants

These pants are so fashionable, they won't even register as sweatpants.

H&M Oversized Hoodie

Oversized Hoodie

Cozy up in this hoodie at home or dress it up and wear it out.

timberland-boots-outfits-sweater

Photo:

Getty Images

If you're looking to add a lot of color on top, then go simple with a neutral-colored pair of Timberlands on the bottom.

Timberland Heritage Boot

If you want to go even bolder, though, we love the gold accents on this pair of Timberlands.

Olivia Rubin Cescy Sweater in Green Check

Cescy Sweater in Green Check

For those who aren't afraid to add color to their wardrobe.

Aimee Kestenberg Famous Double Zip Leather Crossbody Bag

Aimee Kestenberg

Famous Double Zip Leather Crossbody Bag

This berry color somehow pairs nicely with every shade. We don't get it, but we are here for it.

timberland-boots-outfits-trench

Photo:

Getty Images

Adding Timberlands can make any outfit street style-worthy. Even with a simple black base, layering on pearls, a camel trench, and Timbs can make all the difference.

Timberland Cortina Valley Waterproof Boot

Cortina Valley Waterproof Boot

These Timbs are slightly darker than the popular yellow shade.

The Reformation Downing Coat

The Reformation

A good wool coat makes braving the elements bearable.

The Reformation Paige Knit Top

The Reformation

Reformation knits are just so cozy.

Good American Good '90s Jeans

Good '90s Jeans

Staying on theme with '90s jeans.

timberland-boots-outfit-cargo-skirt

Photo:

@aude_julie

A Timbs outfit for the Y2K lovers.

Timberland Women's Polartec® Funnel-Neck Fleece

Women's Polartec® Funnel-Neck Fleece

A Timberland fleece to match your Timberland shoes? Immediately yes.

Zara Cargo Skirt

We are still here for the cargo skirts, btw.

timerland-boots-outfit-leather-leggings

Photo:

@myvoguishdiaries

Timberlands for toddlers are a thing. You know what to do. As for the moms, pairing black Timberlands with faux leather leggings and a white puffer is an easy, yet stylish outfit.

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