Tracksmith Allston Tights ($118)

The Allston’s nylon-elastane blend is breathable, compressive, and smooth. A wide, flat waistband provides a sleek fit.
Whoop Strap 3.0 Fitness Tracker ($288 per year)

Running hard means learning when to back off. Whoop’s simple screenless band uses an app to track workouts. It also uses heart-rate variability and sleep data to tell you how recovered or worked you are, and suggests training adjustments accordingly.
The North Face Etip Recycled Gloves ($45)

The Etip is warm enough for frigid temperatures without being bulky. All five fingers are touchscreen compatible.
Darn Tough Vertex No Show Ultra Light Cushion Socks ($17)

We keep reaching for these socks because of their versatile lightweight merino fabric and just-right compressive fit. The lifetime guarantee doesn’t hurt.
Janji Swift Tech LS Top ($66)

Janji’s slim-fit mock-turtle top is so flattering, you’ll want to keep it on post-run—which you easily can: its wicking poly-merino blend stays stink-free.
HydraPak Recon Bottle ($16)

Don’t forget to hydrate after cold runs. The Recon’s cap twists open to produce a titrated flow, which prevents spillage while you’re drinking. Each bottle features 50 percent recycled material.
Houdini Power Headband ($30)

At eight inches wide, the Power is perfect for those who want more coverage than a headband but don’t like the restrictive feeling of a hat. The four-way-stretch fleece yields a snug, no-slip fit.
Brooks Carbonite Jacket ($180)

Dwindling daylight hours are no reason to skip your run. This water-resistant shell is designed to maximize your visibility, with high-contrast black, white, and yellow coloring, and reflective strips at major movement points: the chest, shoulders, elbows, and wrists.
Oiselle Pockito Bra ($58)

This bra boasts not one but three pockets—perfect for long days when you can’t travel light. We were skeptical at first, but the front center pouch holds a large phone with no bouncing, and the two underarm stashes fit keys, gels, and other sundries.