



Olive jacket, green knit polo & khaki pants
$338For cold days, about 25–40°F · Work · 4 pieces from $50
What to wear to work in winter: a fine knit or shirt under a wool coat or blazer, tailored trousers, and leather boots or loafers, warm on the commute and sharp at your desk. 778 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026 · How to dress for work in winter
Dress for two climates. The commute is cold and wet; the office is often warm and dry. So keep the insulation in the pieces you take off: a wool or cashmere-blend coat, a scarf, gloves and leather boots for the walk. Underneath, wear what looks right at your desk: a fine knit, a shirt, tailored trousers. A merino base layer adds warmth without bulk, and nobody sees it.
Slim leather boots, like Chelsea boots, lace-up boots or heeled ankle boots, look smart with trousers and skirts and handle bad weather. Loafers work when the sidewalks are dry. If you walk through slush, wear boots to the office and keep a pair of loafers or flats under your desk.
A fine-gauge turtleneck or sweater with straight or wide-leg trousers; a knit or wool midi skirt with opaque tights; or a long-sleeve knit dress with a blazer. Heeled or flat leather boots and a long wool coat finish all three. Keep the colors quiet, like camel, grey, navy, ivory and black, and add one richer shade for variety.
A merino or lambswool crewneck over an oxford shirt, flannel or wool trousers, and brown or black leather boots or loafers. An overcoat in navy, charcoal or camel goes over all of it. In a more formal office a blazer replaces the sweater; in a casual one, a quarter zip or a knit polo does.
Match what your office wears in summer, then add texture rather than formality: flannel instead of cotton trousers, a knit instead of a shirt on its own, suede or leather instead of canvas. Dark, warm colors make a simple outfit look more polished than it is.
Build on two or three trousers or skirts in neutral colors and rotate the tops: a turtleneck one day, a shirt and sweater the next, a blazer for meetings. If the coat and boots go with everything underneath, five outfits come from eight or nine pieces.
Yes, in most offices. Sleek leather or suede ankle boots look as polished as loafers with trousers or a skirt. Save hiking-style or very chunky boots for casual Fridays.
Yes. A fine-gauge crewneck, V-neck or turtleneck in merino or cashmere is business casual, alone or over a collared shirt. Chunky cable knits and hoodies read as weekend wear.
Opaque black, navy or charcoal tights in 40 to 80 denier look right under midi skirts and dresses at work. Match them to your shoes or your skirt for a longer line.
A knee-length or mid-thigh wool overcoat in navy, charcoal or camel goes over a suit and a sweater alike. In very cold cities, a plain dark puffer or a parka long enough to cover a blazer works too.
Add warmth underneath, not on top: a thermal or merino base layer, fleece-lined tights or wool socks, and a wool coat with a scarf. Change into lighter shoes at the office if your commute needs snow boots.
778 looks
Filter by brand in searchFor cold days, about 25–40°F · Smart casual · 3 pieces from $38
For cold days, about 25–40°F · Smart casual · 4 pieces from $50
For cold days, about 25–40°F · Smart casual · 4 pieces from $50
For cold days, about 25–40°F · Smart casual · 4 pieces from $50
For cold days, about 25–40°F · Smart casual · 4 pieces from $45
For cold days, about 25–40°F · Smart casual · 4 pieces from $36
For cold days, about 25–40°F · Smart casual · 4 pieces from $58
For cold days, about 25–40°F · Smart casual · 4 pieces from $118
For cold days, about 25–40°F · Work · 4 pieces from $90
For cold days, about 25–40°F · Smart casual · 4 pieces from $138
For cold days, about 25–40°F · Work · 3 pieces from $99
For cold days, about 25–40°F · Work · 4 pieces from $100
For cold days, about 25–40°F · Work · 4 pieces from $100
For cold days, about 25–40°F · Work · 5 pieces from $68
For cold days, about 25–40°F · Smart casual · 4 pieces from $80
For cold days, about 25–40°F · Smart casual · 4 pieces from $120
For cold days, about 25–40°F · Work · 3 pieces from $100
Counted from 35 of these looks.
Black, cream, grey and green come up most often across these looks, so they make an easy base to build on.
Most whole outfits here cost between $289 and $513; the typical one is $389. 24 include a piece on sale. Swap any piece to change the total.
Most pieces come from TOMS, Jachs NY, Thursday Boots, Oak + Fort and Nine West. Each look checks out on the stores' own sites, one store at a time.