Is the Timberland Chillberg fully waterproof?

Yes. The leather upper is waterproof and the seams are sealed. It is not a Gore-Tex boot, so it breathes less than a membrane model.

It runs true to size with a normal width. If you wear thick winter socks, many owners go up half a size.

Is $99.99 a good price?

Yes. At $99.99 at Target as of November 8, 2026, it is near the bottom of its recent range; it usually sells for $130 to $160.

For light snow and shoveled sidewalks, yes. For deep snow or long hikes, a taller insulated boot with a membrane is a better choice.

One pair of boots. Laces come fitted; there are no extra insoles or care products included.

Winter boot prices drop after the holidays and again in late winter clearance. The current $99.99 is already close to those lows.

At Target, for $99.99, 26% under what the other stores charge, as of our latest check.

Rated 4.8 out of 5 from 49 ratings.

10 stores we checked sell it, including Shop Simon, Target, eBay, Poshmark, Depop.

$99.99at TargetObserved at 2:35 AM

26% under what the other stores charge

Compared across 4 stores. Prices are checked against each store and labelled with when.