6 Best Timberland Sneakers, 30+ Shoes Tested in 2023
From construction workers to fashion-savvy guys to stylish rappers, Timberland sneakers are a footwear staple that are beloved by everyone. Over the years, the popular label has built an awesome line-up of hiking-inspired kicks that allow you to go socializing with friends in a coffee shop right after a short hike.
If you prefer a pair of trail-ready sneakers, the Bradstreet Chukka is an excellent choice. For those who advocate for the preservation of the environment, the best-rated Timberland's Davis Square Chukkas will definitely appeal to your taste. These rugged yet fashionable kicks are made of recycled materials.
We’ve rounded up and tested 10+ of the best Timberland sneakers available in the market today. We finalize their rankings and pick our recommendations for this guide.
Table of contents How we test sneakersBest overallBest high topBest mid topBest retroBest valueMost popularComparison
Overview
How we test sneakers
To identify the finest sneaks from Timberland, we check and double-check every parameter of the footwear inside the lab. After gathering essential data, we take the shoes to the city pavement and on the backwoods for a quick hike. These are the steps involved in our selection process:
- Invest our energy, time, and money to perform all the wear-tests ourselves. This ensures that all the reviews remain 100% honest and unbiased.
- Subject the sneakers to a series battery of lab and mechanical tests. We take note of the quality of their materials, durability, real-life fit, comfort, support, versatility, and many more.
- Wear the shoes in athletic events and flaunt them in special occasions and semi-formal gatherings. We assess the shoe’s strengths and shortcomings.
- We also scour hundreds of forums and customer reviews to gather further insights and useful information for our reviews and final rankings.
In the end, we give all the pairs of Timberland sneakers their respective overall ratings. Refer to the CoreScore to check out the ratings of each model in the selection.
Best Timberland sneakers overall
Timberland Bradstreet Ultra Oxford
Amazon
Prime & free shipping
$89
Stadium Goods
$115
Zappos
Running Warehouse
CoreScore
- Top 1% in sneakers
- Top 4% in Timberland sneakers
Pros
- Clean and sharp look
- Versatile for casual wear
- Keeps feet cool on hot days
- Super lightweight
- Grippy for different surfaces
- Supportive and stable
- Supple upper of leather variant
- No break-in time
Cons
- Dark colorways stain badly
- Not well-cushioned
- Pricey
Verdict
The Bradstreet Ultra Oxford from Timberland makes great casual looks as easy as 1-2-3. With its sleek look, it matches different casual styles exceptionally well, elevating outfits with a subtle classy vibe. In addition, it has everything needed to stand with poise, refinement, and composure for any occasion.
Best Timberland high top sneakers
CoreScore
Pros
- Lightweight
- Great foot protection
- Sleek design
- Versatile
- Budget-friendly
Cons
- Narrow forefoot
- Frail material
Verdict
With its lightweight comfort, the Timberland Dausette assures you a smooth ride that goes on for the whole day. Its sleek leather construction has a casual edge that completes the getup, whether for work or play. This shoe is considered to be a stylish sneaker boot that lasts. Overall, its versatility makes the shoe a go-to footwear that probably offers more than expected for its budget-friendly price.
Best Timberland mid top sneakers
CoreScore
- Top 30% in Timberland sneakers
- Top 24% in hiking sneakers
Pros
- Classy silhouette
- Gets compliments galore
- Quality materials and construction
- Super lightweight
- Great durability
- Breaks in fast
- A good investment
Cons
- Upper is prone to stains
- No arch support
Verdict
The Groveton Chukka from Timberland is a shoe that blows away people’s expectations of it. While many have bought it for a specific purpose, it has quickly become an everyday shoe for them because of the sheer amount of style and utility it brings to the table. In addition, its quality construction means that its brilliant looks and refined feel are here to stay.
Best Timberland retro sneakers
CoreScore
Pros
- Empowering style
- Remarkably supple
- Smooth-sailing break-in
- Eye-catching hues
- Lightweight
- Supportive ankle cuff
- Superb durability
Cons
- Difficult to put on
- Could be more flexible
Verdict
What better way to feel posh on a busy weekday than to wear the Skyla Bay Chukka from Timberland? Dubbed by a reviewer as a "wise choice," this trail-ready sneaker will give you the oomph and style you need from the main street to unpaved sidewalks. Having this boot on is like cheating, as it naturally levels ups your look without even trying.
Best value
Timberland Davis Square Mixed-Media Chukka
Amazon
Free shipping
$56
Moosejaw
Free shipping
$90
Eastern Mountain Sports
$90
Zappos
CoreScore
- Top 25% in sneakers
- Top 14% in Timberland sneakers
Pros
- Perfect balance of style
- Comfortable for all-day wear
- Timeless and clean look
- Runs true to size
- Lightweight
- Unique construct
- Easy to style
- Matches any outfit
Cons
- Causes blisters
- Lacks cushioning
- Narrow
Verdict
This Timberland Davis Square Mixed-Media Chukka has treated nubuck repels oil, water, and stains, while the Cordura® fabric resists abrasions. This mid-profile sneaker boot features eco-friendly materials of Cordura® EcoMade fabric and soft fabric lining made from recycled plastic bottles.
Most popular Timberland sneakers
CoreScore
Pros
- Comfortable footbed
- Well-cushioned
- Breathable
- Cushy tongue
- Secured
- Lightweight
- Stable
- Water-repellent
- All-rounder
Cons
- Tight-fitting forefoot
- Lacks style
Verdict
Won’t you love strapping up an athletic-style sneaker from Timberland you can take almost anywhere? Solar Wave Low might just give you that satisfaction. It does its job in keeping the feet engulfed in a durable mesh membrane firmly. The chuck of foam isn’t only eco-conscious but delivers comfortable strides after you’ve crossed a short break-in period.
