What the regular Montauk offers
Timberland’s matching regular Montauk family page describes full-grain leather, an EVA midsole, an OrthoLite insole and cement construction. That provides a concrete basis for comparison with the welted Pit Boss. Construction differences do not establish which lasts longer in your work or which feels better; they identify two actual designs to examine rather than two color choices.
Do not add waterproofing from another Montauk
The title here says Jet Black 10.5M and does not claim waterproofing. Timberland markets a separate Montauk waterproof product, so a shortened search result can obscure the distinction. If wet-route performance is essential, verify the precise style instead of treating all Montauk six-inch boots as one specification.
The useful 10.5 comparisons
Pit Boss Brown 10.5 and Direct Attach Black 10.5 M offer two different reasons to compare: a conventional welted work-boot direction and an explicitly insulated-waterproof direction. They do not become equivalent simply because the nominal length is the same. Choose a fitting trial that reflects the construction question you are trying to answer.
The manufacturer lists steel-toe and EH features for regular Montauk. Those should be matched to the actual pair; they do not imply a puncture-resistant plate or metatarsal guard. The contoured shock-diffusion plate described by Timberland is a structural feature and should not be recast as either of those separate protective components.