When the expensive boot is wrong
This site usually argues for the rebuildable option. Work boots are the clearest case where that argument can fail, and it is worth saying so up front.
A Goodyear welt is only valuable if the sole is what wears out first. If you work around solvents, hot asphalt, sharp steel scrap or concrete dust, the upper goes before the sole does - and a welt you never get to use is money spent on nothing. In those jobs a hundred-dollar direct-attach boot replaced every twelve months is the rational purchase, and we would rather tell you that than sell you a 350-dollar boot you will ruin.
Buy the rebuildable boot when your wear pattern is ordinary: walking, standing, ladders, weather. That covers most trades, most of the time.
The safety rating alphabet, briefly
Safety toe - steel, alloy or composite, all meeting the same impact and compression standard. Steel is cheapest and conducts temperature. Alloy is lighter. Composite is non-metallic, so it does not set off detectors and does not conduct.
EH rated - electrical hazard. The sole provides secondary protection against incidental contact with live circuits. It is a backup, not a reason to touch anything.
Puncture resistant - a plate in the midsole. Worth having on demolition and construction sites, pointless in a workshop.
The sole decision matters more than the toe
Thorogood's MAXwear wedge is one of the most comfortable things you can stand on for ten hours on a shop floor. It is also close to useless on a muddy slope or a ladder rung, because there is no defined heel. Carolina's lug sole and Danner's Vibram do the opposite job.
People buy wedges because they are comfortable in the shop and then wear them outside, which is how the "my work boots are slippery" complaint happens. Match the sole to where your feet actually are.
The honest entries
KEEN's Detroit XT is on this list precisely because it is not a buy-it-for-life boot. It is cemented, so when the sole goes the boot goes - and it is the most comfortable thing here out of the box, with a wide toe box that fits feet other brands do not. Timberland PRO's Direct Attach is cheaper still, genuinely waterproof, genuinely insulated, and permanently un-resoleable: the name of the construction tells you so.
Both are good purchases for the right person. Neither should be sold as a lifetime boot, and the product cards below say so.
Socks are not a footnote
A steel toe chews through the front of an ordinary sock in weeks. Any boot on this page is improved more by a proper boot sock than by spending another hundred dollars on the boot, and the socks in question carry an unconditional lifetime guarantee. The link below is the highest-value click on this page.