Boot construction comes down to how the upper attaches to the sole. Two main ways at the work-boot price points: Goodyear welt and cement (also called direct-attach or cemented).
Goodyear welt. A leather strip (the welt) is stitched to the upper and the insole. The outsole is then stitched to the welt. Two separate stitchings, no glue holding the sole on. This means the cobbler can cut the sole stitching and replace the outsole without disturbing the upper. You can resole a Goodyear-welted boot 2-4 times over its life.
Cement construction. The sole is glued directly to the upper. Cheaper to manufacture. The boot is lighter and more flexible out of the box. When the sole wears or the glue fails, the boot is done — there's no cost-effective way to resole it.
"If your uppers die before your soles, save the money. If your soles die first, spend it."
Most $80-150 work boots are cement construction. Most $250+ work boots are Goodyear welted. The price difference is partly the leather, partly the construction.
When resoling matters. If you wear out outsoles in a year and your uppers are still good, Goodyear welt. Resoling costs $90-120 at most cobblers including Red Wing and Thorogood shops. You buy one $300 boot every 5 years instead of three $130 boots every 18 months.
When it doesn't matter. If you destroy uppers as fast as you destroy outsoles — concrete, chemicals, abrasion — Goodyear welt buys you nothing. Cement-construction boots are the right tool. Buy them, wear them out, replace them.
Look at the bottom of your current pair. If the upper is shot, don't pay for welt construction next time.