April 18, 2024


Unique & Classy

7 Foolproof Ways to on How to Style a Button-Up Shirt This Winter

3 min read

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Understated elegance, stealth wealth, minimalism, whatever you call it, the ultra-crisp button-up shirt transcends trends and seasons. Part of a solid rotation of wardrobe essentials, this menswear-inspired It item has garnered a cult-like following that includes supermodels, from Kendall Jenner and Gigi Hadid, to even Jennifer Lawrence. Like any closet classic, it’s likely that you already own a button-up or two. Now comes the fun part (and where we come in): figuring out how to style it, especially for the colder months. 

In building a foundational capsule wardrobe, a bright white poplin is essential. This style from Acne studios gets the fabric and cut just right. A bold blue button-up is another minimalist must-have, and The Frankie Shop has a great one. Styling-wise, layers are your friend in the winter—think sleek turtlenecks, tissue-thin base layers, and lightweight scarves—for adding warmth and dimension to your look. 

When it comes to the classics, you can never go wrong with a simple stripe. Our Legacy’s blue and white version takes on preppy cool beneath a sweater vest from Gigi Hadid’s brand, Guest In Residence. Meanwhile, By Malene Birger’s tomato red style is the perfect pop of color when paired with a light brown, tailored suit. Below, seven editor-approved ways on how to style a button-up shirt all winter long.

Vogue’s Go-To Button-Ups: 

White Button-Up + Black Turtleneck

A white button-up pairs perfectly with simple wardrobe staples like straight-leg, wool trousers from Dries Van Noten and a soft knit turtleneck from Alex Mill. A leather bomber, combat boots, and chic shades take the look from classic to cool. 

Dries Van Noten

wool-blend straight-leg pants

Alex Mill

Chrissy ribbed turtleneck


relaxed double faced jacket

Le Specs

Outta Love oval-frame sunglasses

Stuart Weitzman

Sondra leather ankle boots

Shop More White Button-Ups:

Isabel Marant

Cylvany cotton-poplin shirt

Striped Button-Up + Sleeveless Vest

Prep school, with a twist. Our Legacy’s striped button-up pairs perfectly with Guest in Residence’s shrunken sweater vest, and an asymmetrical pleated skirt from Sacai. 


pleated pinstriped midi skirt

Guest in Residence

Layer Up ribbed cashmere vest

Radda platinum hoop earrings

Shop More Striped Button-Ups:

Sporty & Rich

striped cotton-poplin shirt

Acne Studios

striped cotton-poplin shirt

Black Button-Up + White Long-Sleeve Top

Go minimalist in layers of simple black and white. The Row’s soft, oversized button-up looks right at home with a sleek black maxi from Matteau and chunky loafers from Aeyde. Bright, white socks add extra style points. 

The Row

Caroline oversized wool shirt


wool-blend crepe maxi skirt

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Blue Button-Up + Black Turtleneck

Pair The Frankie Shop’s blue button-up with Suzi Kondi’s red, cashmere bandana, and a pair of stark, white jeans for a bright and fresh winter outfit.  Extra layers around the neck will keep you cozy and frame your face. 


Bethany boyfriend cargo jeans

Shop More Blue Button-Ups:


oversized long-sleeve shirt


embroidered cotton-poplin shirt

Red Button-Up + Sleeveless Tissue Turtleneck

Add impact to Toteme’s classic suit with a bold pop of red in By Malene Birger’s button-up. Black accessories and a sleeveless white turtleneck anchor the look.

By Malene Birger

Derris button-front shirt


tailored herringbone twill jacket

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Brown Button-Up + Matching Base Layer

Dark brown is this winter’s new classic color. Cos’s chocolate button-down looks so chic with wide-leg, satin trousers from Toteme and a clean, white sneaker. 


oversized cotton-blend shirt


Barb satin wide-leg pants


Prado pearl hoop earrings

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Denim Shirt + Midi Dress

For an added layer—and texture—in between your coat and sweater dress, consider a denim shirt. Wear it open and unbuttoned, or semi-closed with a belt for definition. Suede boots complete the look.  


Remy suede knee-high boots


The Heart Is Not A Metaphor necklace

Shop More Denim Shirts:


Camryn oversized denim shirt

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