Winter is a challenge.

As always, you have to maintain your gruff-but-impeccable appearance, but you also have to navigate cold snaps and abruptly unseasonable weekends without getting too bulky. It’s a tightrope.

The good news is, we’ve got three hard-and-fast rules to keep you unencumbered through the season—and able to navigate any unexpectedly warm days that might pop up along the way.

The Time for Layering Is Over
A month ago, you could put together a warm undershirt, a sweater, a blazer and a scarf, and expect it to add up to outerwear. That time is over. If you try to outfit yourself with enough layers for December, you’ll just end up with strained seams and unsightly bunching. Instead, trust in your winter coat. Underneath that, feel free to dress like it’s September again.

Don’t Be Afraid to Unbutton
The secret of dressing seasonably is that it has more to do with the calendar than the temperature, so don’t ditch the coat just because it’s a few degrees higher than you were expecting. We’re big fans of wearing a large winter coat open, even if you don’t bother to stash your scarf. There’s a braggadocio to it—provided you don’t catch cold.

When in Doubt, a Good Pair of Gloves
The winter triumvirate is hat, scarf and gloves—but if you had to blow your bankroll on a single one, we’d go with the gloves. There’s a limit to how good a hat can ever look, and even the cheapest wool scarf has a certain charm to it. A pair of leather gloves, on the other hand, is like a tailored suit; as you put more money into it, it keeps getting better and better. Budget accordingly.

—R.B.

CONTRIBUTORS

  • Russell Brandom