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.
Who knew pairing Timberlands with a skirt could look so cool?
Shop the kook:
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.
Don't try to resist a pleated mini skirt. You can't.
For a sporty touch.
Everybody needs a plain black baseball cap in their wardrobe.
Adding a statement jacket to a pair of Timberlands, denim, and a white tee can bring the simple look to the next level.
Shop the look:
Doesn't get more classic than this pair of Timberlands.
These Triarchy jeans are super discounted right now, so grab them while you can.
Another staple. Must we say more?
It's giving modern-day Clueless.
This laidback monochrome moment is the perfect cozy weekend ensemble. Throw on your boots, and you're ready to go.
Shop the look:
The ease of Amazon shipping makes these Timberland boots a no-brainer.
You can never have too many pairs of sweatshorts.
Or sweatshirts for that matter.
A cute raincoat can be hard to find, but you can't go wrong with this minimalistic charcoal option.
Hue socks are hands down my favorite.
Try styling the boots with a lace slip dress, a statement jacket, tights, and a turtleneck for an unexpected wintertime ensemble.
Shop the look:
For the wintertime, we love these shearling Timberland boots.
Bomber jackets are going to make their way into 2023.
Simply elegant.
You can layer a black turtleneck under almost anything, and we are so thankful for that.
These opaque tights have a matte finish.
Another statement coat look, but this time with a pink puffer. Timberlands truly are the quintessential winter boot.
Shop the look:
If you are looking to stray away from the classic Timberland boot, try out a Chelsea boot style.
Simple and sleek.
Add to cart.
You can never add too many shades of pink to an outfit. Right?
Tan Timberlands are made to be worn with this shade of green, especially in the fall.
Shop the look:
We're going PRO.
A vest to give your puffer a day off.
These pants are so fashionable, they won't even register as sweatpants.
Cozy up in this hoodie at home or dress it up and wear it out.
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.
Shop the look:
If you want to go even bolder, though, we love the gold accents on this pair of Timberlands.
For those who aren't afraid to add color to their wardrobe.
This berry color somehow pairs nicely with every shade. We don't get it, but we are here for it.
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.
Shop the look:
These Timbs are slightly darker than the popular yellow shade.
A good wool coat makes braving the elements bearable.
Reformation knits are just so cozy.
Staying on theme with '90s jeans.
Pearls can be edgy too.
A Timbs outfit for the Y2K lovers.
Shop the look:
Classic for a reason.
A Timberland fleece to match your Timberland shoes? Immediately yes.
We are still here for the cargo skirts, btw.
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.
Shop the look:
The classics, but in black.
Marshmallow chic.
Faux leather leggings that are actually comfortable.
I Never Wear Uggs, But These 10 Cool Outfits Just Changed My Mind.
-
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)It's finally time to part ways with boring linen dresses.
-
I'm Manifesting a Fashionable Fall in NYC With These 36Replica Store Anniversary Sale FindsFrye, AllSaints, Vince, Coach, and more.
-
The '90s Dress-and-Shoe Pairing It Girls Are Wearing to Parties in East Hampton (Sorry, Flip-Flops, You Weren't Invited)Classic elegance spotted at Gucci's star-studded soirée on Long Island.
-
I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025Apologies are in order.
-
Fall Is Already on My Mind—I'm Prepping My Wardrobe With These 31 ElevatedReplica Store FindsEach piece is chic and on sale.
-
Katie Holmes Is Already Wearing the Boho Boot Color Trend Fashion People Everywhere Will Wear This FallNot once, but twice.
-
Leopard Print Is Fine, But This Is the Unexpected Shoe Print Fashion People Are Already Wearing on RepeatControversial yet chic.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local BistroSorry, ankle boots, but it's not you.
