Timberland Boots: From the 1973 Yellow Boot to Platforms and Chelseas

Timberland Boots: From the 1973 Yellow Boot to Platforms and Chelseas

Timberland boots began as a waterproof work boot in 1973, and this edit sorts the 6-inch classics, platform and heeled pairs, and chukkas, hikers and chelseas by how they wear. I say when I would reach for each one and what to check in the fitting room.

In 1973 the Abington Shoe Company launched the Original Timberland 8-inch boot, the yellow one, and the brand says the 6-inch version followed three years later. The company's story starts with a founder, Nathan Swartz, who took full control of the Boston-based Abington Shoe Company in 1955 and developed waterproof boots with his son Sidney, who then went on to brand them. The boot was made for hard-working New Englanders, inspired by form and function, not trends and runways. I love that. Something built for wet job sites ended up in everyone's closet.

 

That is why I trust Timberland boots more than most shoes with a logo. The details are still practical: brass eyelets, four rows of stitching, a padded leather collar and an anti-fatigue footbed. The look has stayed put while the colors have multiplied, so you can wear the classic shape and still pick the version that suits your wardrobe.

 

Start with the 6-inch pairs. The Premium Waterproof Boot in black is the city one, with PrimaLoft insulation and a chunky lug sole, and I would wear it with straight jeans and a long coat. The Premium 6-Inch in gray suede has a caramel sole and tonal laces, which feels softer next to a gray knit dress. The wheat 6" Premium Waterproof Boots are the original look, and the Stone Street wheat pair puts it on a platform sole. If you want a pop, the dusty red nubuck and the dark green croc-embossed pair both work with plain denim, and the navy canvas pair works with gray and camel. Try the laces loose first, then snug, and walk up a flight of stairs before you decide.

Collage of 6-inch lace-up boots, platform and block heel boots, and chelsea, chukka and hiking boots, and a mood photo of wheat lace-up boots with white socks on a bench

Timberland 6-inch lace-up boots

Platforms and heels, tested

Height is a sneaky thing on a boot, so stand in them for a full minute before you decide. A platform sole changes how a pair walks far more than a heel does, and the boots in this section split between the two ideas.

 

The Stone Street Platform Hiking Boot in wheat is the tallest statement here, and I would wear it with a mini skirt and thick socks. The Stone Street Platform Boot in gray nubuck has a corduroy ankle and heel that I find very charming with wide cord trousers. For the cold weeks, the warm-lined gray pair has a cream shearling collar, and the Stone Street Waterproof Platform Boot in jet black has PrimaLoft insulation and a memory foam footbed. The light pink mid boot with moc-toe stitching on a gum platform sole is the playful one, and I would keep the rest of the outfit quiet around it.

 

If you want a heel rather than a platform, the Allington Block Heel Bootie in black and the Allington Heights 6" in taupe nubuck are the two I would try. The bootie has an Ortholite footbed and a recycled-plastic lining, and the taupe one has a stacked heel with hex eyelets. Both work with a slip skirt or a cropped trouser.

 

What I would skip: a thick platform for a day of constant stair climbing, unless you have already walked in it at home.

Heeled and platform Timberland boots

Chelseas, chukkas and hikers

Check the shaft before anything else: how a boot closes at the ankle tells you how it will sit under a hem. This last section is about boots that are not the classic 6-inch, and each one asks for a different trouser.

 

The chelsea boots are the sharpest. The Premium Mid Chelsea in light brown full grain has dual stretch gores and a steel shank for arch support, so it is the one I would wear to the office with tailored pants. The Brimfield Chelsea in light beige suede has an OrthoLite insole and a lugged sole, and the Rowan Way pull-on in tan nubuck is the easy version for mornings with no time. Pull each one on and off a few times in the fitting room, because a gore that is too tight gets annoying fast.

 

The Rowan Chukka in light taupe nubuck is lined in faux-shearling and works with cuffed jeans. For hiking looks, the Authentic Waterproof Mid in wheat has a roll-top and fleece lining, and the White Ledge in brown suede is waterproof and insulated. The Mt. Maddsen pair is the louder one, with blue panels, orange laces and purple lining in the tan version, and a plain black leather version with D-ring lacing and a logo patch. Wear the hikers with a puffer and leggings, and keep the colors close in tone. If you want the taller original, the Premium 8-Inch Waterproof Leather Boot is the 8-inch cousin of the 1973 yellow boot, and the Euro Hiker in wheat is the lighter trail pair.

Timberland chukkas, hikers and chelsea boots

How I would choose a pair

Pick the job first. If you want the original, the wheat 6-inch is the answer. If you walk a lot in rain, take the black waterproof pair. If you want height, try a platform and a block heel on the same day.

 

Then try a few on with the socks you actually wear. Walk, sit, and take the stairs. The best pair is the one you forget you have on.

 

I keep coming back to the first idea: a boot made for a wet New England job site that still looks right in a city. I think that is the whole appeal. If you want to keep browsing, I also put together Frye Campus Boots Dupe and Burgundy boots.