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19 Polished Ways on How to Wear Dresses With Jackets This Fall

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According to calendars, there are a few precious weeks of summer left to enjoy. But lately, many New Yorkers have noticed a crisp, cool breeze while walking the city streets. It’s beginning to feel a lot like fall. Specifically and sartorially, it’s beginning to feel like the best part of fall: the transitional season. The early weeks of September are one of the most exciting times to get dressed. It’s finally time to pull out the new jackets and jeans that are burning a hole in the back of your closet, but your favorite summer staples can still stay in play.

One of our favorite transitional outfit ideas is the simple combination of a jacket (be a blazer or ladylike jacket) and a dress. Sure, the two-piece formula may seem obvious, but much like its summer counterpart (dresses and sneakers!), it’s a versatile look that can be worn in endless iterations. The best blazer and dress combos are lessons in contrast—feminine versus masculine, long mixed with short, and business meets casual. For our favorite ways to wear it this fall, discover our edit below.

Vogue’s Fall Dress Wish List:

Vogue’s Fall Jacket Wish List:

Jil Sander

wool-blend and satin midi dress

The Row

Alda double-breasted Cady blazer

Khaite

Hencil knitted midi dress

Courrèges

Officer Prince of Wales checked tweed jacket

Posse

Raquel floral cotton-silk maxi dress

Staud

Corrine single-breasted suede jacket

Róhe

pinstriped wool-blend twill wrap blazer

Diotima

Pocomania open-knit cotton maxi dress

Cos

striped midi T-shirt dress

Proenza Schouler

Bella sleeveless maxi dress

Loulou Studio

Lavena single-breasted collarless jacket

Loretta Caponi

Cassiopea cotton-poplin maxi dress

Dôen

Rosaria floral silk-blend midi-dress

Miu Miu

logo-embroidered mohair blazer

Ulla Johnson

Kalena draped crepe midi dress

Zara

oversized crop pinstripe blazer

Matteau

gathered drop-waist organic cotton maxi dress

St. Agni

jersey turtleneck maxi dress

Nour Hammour

Zakary belted paneled leather jacket

Esse Studios

strapless knit maxi dress

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