19 Chic and Smart Ideas on How to Wear Dresses with Blazers This Winter

Dresses with blazers is a proven closet combination that thrives during the transitional fall-to-winter months, just ask Katie Holmes. The actress has long been a fan of the look, sporting an oversized black blazer atop a fringed white dress just last season. Even Vogue’s very own executive fashion & beauty director, Lisa Aiken, is known to try out the trend, layering Saint Laurent’s Prince-of-Wales-printed blazer atop a dainty lace dress during New York Fashion Week. The juxtaposition of the two styles, one masculine, and the other feminine, perfectly defines how the modern woman wants to dress today: chicly and smartly. 

When it comes to choosing your winter dress of choice, look to notable knit pieces, printed maxi styles, turtleneck designs, or even a statement red dress. (Proenza Schouler White Label, Toteme, Cos, and Dôen all have options that are too good to pass up.) 

With your bases covered, now it’s time to turn your attention to the other half of this chic outfit combination—the blazer. There is Reformation’s “luxury” faux-leather blazer that adds an instant edge to your entire look or Mango’s suede style for another textural take. A solid black blazer is forever timeless in your wardrobe, whether slim-fitting or oversized like these from Wardrobe.NYC, H&M, and Acne Studios. Houndstooth and checkered blazers go well atop dresses from Polo Ralph Lauren and Altuzarra, while & Other Stories’ slate gray pinstriped blazer stands alone against Sacai’s two-in-one turtleneck dress. Staying true-to-the-classics, Everlane’s camel blazer is a no-brainer in any fashion darlings’s wardrobe, pairing ever-so perfectly with a striped cashmere knit dress from Jardin des Orangers.

This winter, dresses with blazers is a chic closet combination that is stylish as it is smart. Below, shop 10 dresses with blazers outfit combinations and expect sartorial success every time.

Proenza Schouler

Rachel striped midi sweater dress

Sea

Lorraine lace-trimmed silk-satin midi dress

Proenza Schouler White Label

Polo Ralph Lauren

long-sleeve turtleneck dress

Saint Laurent

Prince of Wales-check wool double-breasted jacket

Dôen

Obelia corded lace-trimmed silk-satin midi dress

Massimo Dutti

houndstooth double-breasted blazer

Polo Ralph Lauren

Bluen intarsia-knit turtleneck maxi dress

Bottega Veneta

Knot double-breasted oversized blazer jacket

Toteme

belted gathered crepe maxi dress

Reformation

Veda Dalia relaxed-fit leather blazer

Ulla Johnson

Magnolia two-tone sunburst knit midi dress

Dôen

Harlow checked woven midi shirt dress

Toteme

Petite stretch-crepe blazer

Cos

pleated turtleneck maxi dress

Jardin des Orangers

striped wool and cashmere midi dress

J.Crew

Collection tipped tuxedo blazer

Proenza Schouler

Carol striped chiffon midi dress

Toteme

twisted-seam velvet midi dress

& Other Stories

oversized pinstripe blazer

Altuzarra

Denning ribbed-knit maxi dress

Loulou Studio

Senja pinstripe cashmere blazer

Lisa Yang

Finley ribbed cashmere midi dress

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