Late December is dead at the shop on the calendar — the holidays slow everything — but it's the right time to do an inventory of what you're going to wear in January. The goal is not to buy a fresh everything. It's to be honest about what's about to fail and replace it before it fails on the job.
What we tell customers to look at, in order:
Boot soles. If your wedge or lug is glassy, your traction is gone. New boots, or a resole if the upper is still good. A Thorogood resole at the right cobbler runs $80-120 vs. $230 for a new pair. Worth it if the upper has another year. Not worth it if the upper is creased and cracked.
Boot leather, around the toe and heel. Cracks in the leather are slow leaks for water. If your boots cracked in November, January is going to be miserable.
Bib zippers. The single most-failed point on insulated bibs is the front zipper. Test it now. A bib that won't zip in January is a bib that's not on you.
Glove insulation. Insulated gloves compress over a season. The pair that was warm in November is colder by January. If your hands are getting cold by 9 AM in 30-degree weather, replace the gloves.
Watch caps. Watch caps are cheap and they pill, stretch, and lose elasticity. Replace yearly. $14.
Wool socks. The four pair you started winter with should still have life. The two pair you've been wearing for three years don't. If you can see your heel through the wool, swap.
Base layers. Wool and synthetic base layers degrade over heavy use. If your merino tops have holes in the armpits or the elastic in the cuffs is shot, swap. They're $50-110 each but they last 2-3 winters.
Hi-vis. Reflective tape on a heavy-use hi-vis loses 30-50% of its retroreflectivity after a year of work and washing. If your hi-vis is a year old and you're working in low-light, swap.
What you don't need to swap year-end: parkas (these last 4-7 years if cared for), bibs (3-5 years), good leather work gloves (1-3 years).
Most year-end cleanup runs $150-300 if you're in average shape. Less if you've been keeping up. More if you've been kicking the can on a few items. December is the month to be honest about it.