You don’t want to be caught underdressed when the windchill picks up, nor do you enjoy having to peel off multiple sweaters every time you cross a doorstep. What you do want: effortless, temperature-regulating combinations that don’t require much forethought each morning. Below: a guide to keeping things warm (and intentional) now and all through winter.

ON THE CLOCK

An asymmetrical hemline on a crisp-collared cotton button-up adds intrigue to a failproof work look. Particularly when peeking out from underneath a chunky merino knit.

ON THE TRAIL

Puffer vests and fleecy base layers are made for each other. It’s a toasty yet breathable equation that will keep you from overheating as you get your heart rate up. Next, seal in warmth from head to toe with a balaclava and shearling-lined boots.

ON THE TOWN

A faux-leather jumpsuit, in addition to being the epitome of sexy sleekness, acts as a sort of second skin (a godsend on a winter’s night out). Emphasize the polished finish with contrasting textures—a houndstooth coat here, a plush neck warmer there…and, of course, something sparkly at the ears.

ON THE WEEKEND

Big cashmere pullovers and chunky boots are a day-off given. What isn’t: intarsia zigzags and bright-red soles that will pull and hold gazes wherever you take them. Reinforce the cozy under (with a thermal tee) and over (with a bouclé coat).

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