Most working guys don't replace gear continuously. They replace it in waves, twice a year. The big winter buy in October-November, and the half-time refresh sometime in May-June. The half-time is what catches people off-guard, because the cold-weather buy is calendar-driven, but the half-time is wear-driven.
What gets replaced at half-time, in order of frequency:
Boot insoles. This is the cheapest, most-overlooked item on the list. A pair of work boots wears out the insoles in 4 to 6 months of daily use, well before the boot itself is done. A $30 set of replacement insoles — Superfeet Green or the Carhartt Insite at $25 — extends the boot's life by 6+ months and fixes the dead-foot feeling guys complain about by April.
Gloves. Whatever the rotation looked like in March, it's smaller now. We see guys come in for two new pair of leather-palms and three new pair of nitrile-dipped knits at the half-time. Total around $80.
Socks. This one always surprises customers. Wool socks that came in at $26 a pair in October are heel-thinned by April. A four-pair wool-sock refresh at the half-time is $80-100. If you've been in the same wool socks since October and you can see your foot through the heel, replace them.
Pants. Knees blow out, double-fronts wear through. The Carhartt B01s a guy started the season with in March will have repairable spots by June and unrepairable spots by August. A fresh pair at half-time at $55 is the move.
Belts. Belts are forgotten. A leather work belt that started fresh in October is cracking by May. $30 for a fresh one.
Hi-vis. Reflective tape peels and sun-fades through the spring. By June, a March-purchased hi-vis t-shirt is half as visible as it was when it was new. Replace it. $30.
What does NOT need replacing at half-time, usually: boots, jackets, bibs, hats. These are season-spanning items and the major replacement cycle is October-November.
Average half-time refresh for one guy across all trades: $250-350. Less than a winter kit, more than people expect. Plan for it.