11 Winter Work Outfits To Wear On Repeat All Season Long

The centerpiece of any working wardrobe, regardless of the season, is a great dress. This winter, we’re layering Joseph’s two-toned maxi underneath H&M’s long gray coat. Polish off the look with Massimo Dutti’s preppy penny loafers and a roomy suede tote from Toteme. Wrapping up in Cos’ checked scarf adds a pop of color—and extra warmth.


oversized mohair-blend scarf

Err on the Edgier Side in a Sleek Leather Pant

Esse Studios


Proenza Schouler

Soho patent-leather platform loafers

Embrace the Statement Dress

The Frankie Shop


Park medium grained-leather tote

Anagram alpalca-blend scarf


Stuart Weitzman

collarless single-breasted wool blazer

Isola recycled platinum-plated hoop earrings

Mara croc-effect leather notebook

Gray on Gray Is a Chic Closet Combo to Consider


The Row

Yuliana leather knee boots

These days, no modern workwear wardrobe is complete without a masterfully minimal midiskirt. Esse Studios’ patent leather pick brings polished edge, especially when styled with a classic polo sweater from Veronica de Piante and Khaite’s suede Marfa booties. Then, there are statement skirts from Victoria Beckham and Cos that are equally essential. Nine-to-five dresses from Proenza Schouler and Joseph are all-in-one-outfits not to shy away from, either. Styling-wise, top off the looks with a pair of sturdy knee-high boots and a warm winter coat. Speaking of outstanding outerwear options, we’re sporting Proenza Schouler’s shearling leather jacket with a matching trouser from Toteme and Banana Republic’s puffer coat with a pair of lug-sole boots from Chloé built for traction.

Toteme’s green V-neck sweater will immediately alleviate any winter blues you may have. Styling-wise, wear the It item with Victoria Beckham’s asymmetrical jean skirt and a camel peacoat from Zara. Then, keep things sophisticated in a pair of patent knee-high boots (also from Toteme) and Burberry’s Knight bag.

Veronica de Piante


Of all the workwear trends, cinched-waist blazers, sweaters, and silhouettes are topping our list. Try out Joseph’s belted sweater to see for yourself. Styling-wise, layer it over a crisp white shirt from & Other Stories and Theory’s minimalist maxiskirt. Like the lug-sole boot, a pair of chunky loafers ensures that this workwear outfit stands up to the elements in style.


A sleek leather pant elevates any ensemble, no matter what it’s paired with. For workwear, we suggest styling Toteme’s pair with a statement red turtleneck from Zara and, to match, a shearling leather jacket from Proenza Schouler. Speaking of outfit elevators, sling-back kitten heels from St. Agni will take the look to new heights.


Moon striped cotton-jacquard shirt

Avio cotton-poplin trench coat

It’s Sweater Weather! A Polished Polo Is a Prized Pick

merino wool turtleneck top

How to Brave Wind, Sleet, and Snow in Style

long wool-blend double-breasted coat

Oh, the ever-enduring allure of the winter white outfit! At the office or elsewhere, nothing is quite as chic as Toteme’s faux fur coat paired with a J.Crew cable-knit sweater and The Row’s trousers. Beige accessories from Massimo Dutti, Loewe, and Manu Atelier add depth to the final look.


ribbed cashmere-blend balaclava

The Strong Suit


Flow Runner brushed suede sneakers

A Cinched-Waist Sweater Is Totally Timeless

The Slim crinkled patent-leather knee boots

You Can Never Go Wrong With a Classic Button-Up Shirt

Coco cotton-jersey T-shirt

Estella ribbed wool sweater

Spencer suede square-toe loafers


When it comes to easy outfit elevation, a timeless trench coat is a closet classic for a reason. This winter, layer one from The Row with gray outfit separates courtesy of Khaite, The Frankie Shop, and Uniqlo. Other tailoring essentials include Victoria Beckham’s matching wool suit and a cinched-waist sweater from Joseph, which pairing equally well with Loewe’s city sneakers as Stuart Weitzman’s chunky loafers.

high-rise leather wide-leg pants


Milos faux-leather maxiskirt

Alps long satin puffer coat

Strong suiting and workwear go hand-in-hand. This winter, opt for Victoria Beckham’s wool suit and underneath, layer in & Daughter’s chunky turtleneck. Meanwhile, Loewe’s city sneakers make for easy, chic commute; same goes for By Malene Birger’s bright white tote bag and an Acne Studios’ mohair-blend scarf.

Emme Parsons

The Frankie Shop

The Row

leather tote bag with a crackled finish


Carol striped chiffon midi dress

x Anna October patchwork cable-knit crewneck sweater



oversized wool-blend sweater

Believe it or not, the “groutfit” (an all-gray outfit) is a staple in any fashion darling’s wardrobe. Just this past fashion month, many a chic insider could be spotted sporting the new neutral tone. This winter, get the look courtesy of Khaite, The Frankie, Uniqlo, and The Row. Your working wardrobe has never been this smart—or timeless!

Massimo Dutti

Drop large recycled sterling silver earrings

A Welcome Punch of Color

100% cashmere knotted sweater

Alina high-rise wool-blend trousers


HEATTECH ultra warm high-neck T-shirt

Oh, and since most of us are already in a big holiday mood, each of these winter work outfit formulas transitions from commute to cocktail flawlessly. Below, 11 winter work outfits to wear on repeat all season long.

A Long Knit Dress Is Clean and Simple

Gelso pleated straight-leg pants

Nikola double-breasted belted trench coat

Stuart Weitzman

Even in the dead of winter, a classic button-up is a working wardrobe staple. For added coverage, we recommend layering in Cos’ second-skin turtleneck underneath. To match, finish off the look in a pair of winter white jeans (also from Cos) and The Frankie Shop’s belted khaki coat. A pair of ballet flats from Khaite adds a sweet touch.

What to do when the snow is falling, the roads are icy, and the temperatures are dipping below freezing? Bundle up in Banana Republic’s puffer coat and then slip into a pair of shearling-lined boots from Chloé, which have grippy soles built for slippery roads. Meanwhile, separates from H&M and Cos are warm as they are chic.


The Row


Paris faille sling-back pumps

Fintra wool turtleneck sweater

Bremy wool straight-leg pants

Victoria Beckham

The Row

Is there anything better than cozying up in a statement sweater? We think not. We especially love the combination of Veronica de Piante’s polished polo with Esse Studios’ leather midiskirt. Other chic outfit additions include Zara’s classic black coat, a pair of suede booties from Khaite, and Aesther Ekme’s slouchy tote bag.

Judd cropped shearling-trimmed leather jacket

St. Agni

Raina shearling-trimmed ankle boots

Michaela Fair Isle cardigan


‘Tis the season for festive dresses! Go from office party to cocktail party in Proenza Schouler’s animal-printed chiffon number. Complete the look courtesy of an & Other Stories black blazer and a pair of slouchy knee boots from Stuart Weitzman. Winter accessories from Banana Republic and Everlane are not to be missed, either.

By Pariah

Proenza Schouler

The Cashmere Fine Rib Beanie

Winter White Is Your New Neutral

Banana Republic

Victoria Beckham

If you’ve been following along with our winter fashion guides, then it’s likely that you already have a solid roster of workwear essentials lined up–think crisp shirting, sleek pairs of smoking loafers, knit dresses, structured wool overcoats, the list goes on. Now comes the fun part (and where we come in): styling your winter work outfits. Since it’s fashion we’re obsessed with after all, you can also expect an It item or two in the mix, like Khaite’s cult-classic Fair Isle cardigan, a fabulous faux fur coat from Toteme, and Zara’s statement red turtleneck.