A man wearing a timberland outfit with a brown jacket, pants and boots

Timberland

$$unisex
StyleWorkwear / HeritageGorpcore / OutdoorStreetwear
Known forBootsFootwear
Origin · Abington, United StatesMade in · USA & AsiaFounded · 1952

Timberland makes waterproof leather boots, footwear and outdoor apparel, built around the 6-Inch Premium "yellow boot" that became a hip-hop and streetwear staple. A VF Corporation subsidiary since 2011, it operates from Stratham, New Hampshire, selling work boots, chukkas, boat shoes, hikers, outerwear and accessories, with recycled-material and responsible-leather sourcing programs. Recent collaborations include Telfar and Supreme in late 2025 plus a second Jacquemus capsule reworking the 3-Eye Lug boat shoe for summer 2026; its FW25 campaign featured Spike Lee and Skepta.

You might also like
A man looking off in the distance on a snowy mountain wearing an orange Norrona jacket89% match

Norrona

$$$Outdoor / TechnicalLysaker, Norway

Norrona strongly aligns with Timberland in their focus on high-quality, durable outdoor gear with a neutral palette and similar price range, making them suitable for similar activities.

See all 30 brands like Timberland

How Timberland fits
CategoryRunsShapeLengthSize adviceConfidence
Hoodies & sweatshirtsslightly largerelaxed and roomy, built for layering over a tee or flannelregular body with generous sleeve lengthStick to your normal size for a relaxed look, or size down for a cleaner fit.medium
Shirts & overshirtsslightly largerelaxed regular fit, especially on flannels and overshirt-style shirtslonger hem intended to be worn untuckedOrder your usual size unless you want a fitted look, in which case size down.medium
Trousers & pantstrue to sizestraight, utility-influenced cut with room through the thigh and seatregular inseam, often sold in fixed lengths that may need hemmingTake your measured waist size; the leg is roomy by design.low
Jeans & denimtrue to sizestraight to relaxed workwear denim, rarely slimregularBuy your normal waist and expect a straight, non-tapered leg.low
Jacketsslightly largeroomy outdoor cut with space for mid-layersregular to slightly long, with longer parka optionsStay with your usual size if you layer; consider sizing down if wearing it over just a tee.medium
T-shirts & graphic teesslightly largeboxy, straight-cut body with a fairly wide sleeveregular, occasionally a touch longSize down if you prefer a trim, close-to-body tee.medium
Does Timberland run big or small?

Timberland fits slightly large. Take your usual size for a relaxed outdoor fit, or size down one if you want anything close to a modern slim silhouette. Timberland apparel is generally cut for layering and outdoor wear, so most shoppers find it true to size but noticeably roomier and boxier than fashion-oriented brands; the boots themselves are the well-known exception, widely reported to run large with a half-size down recommended.

How does Timberland fit?

Timberland apparel is generally cut for layering and outdoor wear, so most shoppers find it true to size but noticeably roomier and boxier than fashion-oriented brands; the boots themselves are the well-known exception, widely reported to run large with a half-size down recommended. Overall shape: relaxed, workwear-leaning regular fit with generous room through chest and body.

How do Timberland hoodies & sweatshirts fit?

Timberland hoodies & sweatshirts fits slightly large. Stick to your normal size for a relaxed look, or size down for a cleaner fit. Shape: relaxed and roomy, built for layering over a tee or flannel.

How do Timberland shirts & overshirts fit?

Timberland shirts & overshirts fits slightly large. Order your usual size unless you want a fitted look, in which case size down. Shape: relaxed regular fit, especially on flannels and overshirt-style shirts.

How do Timberland trousers & pants fit?

Timberland trousers & pants fits true to size. Take your measured waist size; the leg is roomy by design. Shape: straight, utility-influenced cut with room through the thigh and seat.

Directional fit consensus summarized from public sources with AI — a starting point, not a guarantee. Confirm with the product's own measurements before buying.

Not sure what size to buy?

Paste a Timberland listing's measurements and compare them to something you already own.

Check fit with Timberland

Bought Timberland? Share how it fit