9 Chic City Outfits That Make Dressing for Winter Effortlessly Easy

Back to the power of a winter white poplin: no cold-weather city outfit is complete without one. As modeled below, the closet classic serves as the ultimate fashion foundation, to be worn layered underneath a cashmere crewneck from La Ligne and then finished off with a mohair-blend coat from Ganni. Similarly foundational, is a forever chic cable-knit sweater, like this one from Dries Van Noten. Styling-wise, pair the notable knit with Victoria Beckham’s asymmetrical denim midiskirt and Proenza Schouler’s over-the-knee boots. And since we’re talking about layering, here, throw on Mango’s shearling jacket for a downtown feel. If you haven’t already heard, red is undoubtedly the color of the winter season. Take part by layering Cos’ statement turtleneck underneath a Bode Fair Isle cardigan to match. A perfect camel peacoat from Massimo Dutti is also crucial to the final look. 

Then, there are more casual, but cool layering essentials to invest in, like an oversized hoodie from & Other Stories to Agolde’s corduroy overshirt. On the opposite side of the sartorial spectrum, dress up your newly minted layers with a croc-embellished patent boot from Staud or a leather midiskirt from Zara. Consider the below Vogue’s lesson in layering a.k.a. 9 super-chic city outfits that make dressing for winter effortlessly easy.

Never Underestimate the Power of a Crisp Button-Up Shirt

Nothing is more foundational in a wardrobe—or a chic city outfit—than a crisp white button-up shirt. This fall and winter, layer it underneath La Ligne’s plum-colored cashmere crewneck and a wool-blend coat from Ganni. The result? A perfectly polished look each and every time. Accessory-wise, slip into a pair of penny loafers from ATP Atelier and carry Toteme’s sleek shoulder bag. 

La Ligne

Mini Toujours ribbed cashmere sweater

Zara

pleated straight-leg pants

Toteme

T-Lock large grained-leather cross-body bag

A Chunky Cable-Knit Sweater Is Forever in Style

A wardrobe staple that stands the test of time? A chunky cable-knit sweater. From Dries Van Noten, this one is a prized pick. Cool-ify the classic with a jean midiskirt from Victoria Beckham and Proenza Schouler’s over-the-knee boot. For one extra layer, drape Mango’s oversized shearling jacket across your shoulders. Cozy, yet chic accessories include The Row’s ’90s bag and a checkered mohair scarf from Cos. 

Mango

faux shearling-lined jacket

Cos

oversized mohair-blend scarf

A Hint of Red Is This Season’s Hero Item

No fall hue is trending now quite like cherry red. Case in point? Cos’ statement turtleneck layered underneath Bode’s fabulously festive Fair Isle cardigan. Other chic outfit additions include a Massimo Dutti khaki peacoat, slouchy blue jeans from Re/Done, and a pair of metallic loafers from Mansur Gavriel. 

Cos

merino wool turtleneck top

Bode

Oslo Fair Isle intarsia cardigan

Khaite

Maeve small suede handbag

An Oversized Hoodie Is Your Best Friend

As showcased on the Miu Miu fall 2023 runway, an oversized hoodie is your best friend. Sartorially speaking, of course. It strikes the perfect balance of casual and cool, especially when layered underneath an oversized blazer, like this one from The Frankie Shop. Add in Citizens of Humanity’s long-sleeve tee for a bit more coverage; then slip into a pair of sleek black leggings from Toteme to finish the look. 

Toteme

Cork stretch-jersey leggings

Citizens of Humanity

Adeline ribbed stretch organic top

Agnelle

embellished leather gloves

From Classic to Cool-Girl, Corduroy Is in–and in a Major Way

On days where a heavy winter coat is thankfully not needed, opt for a cozy corduroy overshirt instead. From Agolde, the workwear staple pairs perfectly well with a matching trouser (also from Agolde). And to add one more layer into the mix, because why not, slip on Khaite’s denim Jinn shirt underneath. Styling tip: leave both overshirts un-buttoned, so that each layer shines through equally. Accessory-wise, a pair of stompy boots from The Row is just perfect. 

Agolde

Odele cotton-corduroy shirt

Agolde

Low Slung Baggy cotton-corduroy wide-leg pants

Khaite

Jinn oversized denim shirt

A Super Snuggly Turtleneck Is the Ultimate Style Staple

Who could resist snuggling up in Cos’ wool turtleneck sweater this winter? However, if you’re worried about itchiness, layer in a crewneck top from Bite Studio underneath just to be on the safe side. For an elegant evening look, pair the notable knit with a leather midiskirt from Zara and Khaite’s knee-high Marfa boots. Finishing touches include an & Other Stories double-breasted wool jacket and Loewe’s signature fringed Anagram scarf. 

Cos

mouliné wool turtleneck sweater

& Other Stories

double-breasted wool jacket

Bite Studios

crewneck long sleeve T-shirt

Khaite

Marfa 25 leather knee-high boots

When in Doubt, Go Gray

As modeled by the street style scene, fashion has officially gone gray! One of our favorite looks starred a gray V-neck sweater, like the one below, with a plain, but perfect white tee layered underneath. A feminine twist if you ask us. Finish off the look with Massimo Dutti’s flared midiskirt to match and a toggled-adorned jacket from Gap. Ensemble elevators include The Row’s ivory kitten-heel mules and a knit beanie from Khaite. 

The Row

Tommy cotton-jersey T-shirt

Khaite

Alpina Fair Isle cashmere beanie

Blazers With Dresses Is a Classic Closet Combination

Layering a dress underneath a boxy blazer is a closet classic season after season. This fall and winter, we’re taking part with Mango’s ribbed turtleneck midi and Blazé Milano’s gold-buttoned blazer. For one extra layer, add Everlane’s cashmere crewneck into the mix. You could wrap it around your shoulders or even tie it around your waist. The stylistic opportunities are endless! 

Staud

Cami croc-effect leather knee boots

Everlane

The Alpaca Cropped Crewneck Sweater

Lié Studio

The Klara gold-plated earrings

Saint Laurent

Le Anne-Marie small patent-leather shoulder bag

A Simple Striped Turtleneck Goes a Long Way

A simple striped turtleneck goes a long way no matter which way it’s styled. This season, we’re wearing ours tucked into a pair of winter white jeans from Staud and layered under The Frankie Shop’s oversized wool coat. For added flare, step into a pair of Western-inspired booties from Aeyde and loop in Saint Laurent’s silver statement belt. 

Massimo Dutti

long-sleeve striped T-shirt

Aeyde

Belinda leather ankle boots

Everlane

The Cashmere Fine Rib Beanie

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