Are these boots actually waterproof?

Yes. The leather upper is treated and the seams are sealed, so water stays out in rain and shallow puddles. They are not meant for standing in deep water.

How do they fit compared with sneakers?

They fit true to size for most buyers. The medium width suits an average foot, and thick socks may call for a half size up.

How long does the break-in take?

Expect a stiff first week or two. The leather softens with regular wear, and most owners report a comfortable fit after that.

The rubber outsole is stitched and glued to the leather upper, so a cobbler can replace it. That extends the life of the boot well beyond the first sole.

What is the difference from the standard Timberland 6-Inch Premium?

This is the same 6-inch silhouette in black leather with a waterproof build. The Premium line uses similar construction, so the choice comes down to color and leather finish.

Are they good for winter?

They handle cold, wet and light snow well and the lugged sole grips. They are not insulated, so very cold days need thick socks.

Where is the Timberland Classic 6" Waterproof Boot cheapest?

At eBay, for $138.95, 23% under what the other stores charge, as of our latest check.

What do buyers say about the Timberland Classic 6" Waterproof Boot?

Rated 4.7 out of 5 from 3 ratings. Buyers like: Reviewers call them dream shoes; Repeat buyer on their 3rd pair from the store; Right product with right fit.