J. Crew V-neck Dress in Super 120s Wool
A closet classic, this dress nips in at the waist and hits just below the knee to create a slimmer-looking middle and longer-looking legs. Made from soft merino wool, this work-ready pick will keep you warm from fall all the way through winter. Also available in three other colors.
To buy: $188; jcrew.com.
Moon River Ruffle Midi Dress
Tassled ties and a ruffled, prairie-style shape make this frock effortlessly romantic. Wear it with a pair of suede tall boots and your favorite leather jacket for a little edge.
To buy: $100; nordstrom.com.
Zara Printed Midi Dress
This dark floral print works in a myriad of situations—try it under a blazer with a pair of sleek pumps for the office, or add some statement jewelry for an unexpected evening look.
To buy: $70; zara.com.
Abercrombie & Fitch Pleated Midi Dress
With its airy, chiffon pleats, this pretty slip dress looks great now (while the weather is still warm) worn alone with summer sandals. Come cooler temps, the rich burgundy hue will look just right layered over a thin black turtleneck. Also available in four other colors.
To buy: $78; abercrombie.com.
Banana Republic Floral Tie-Neck Shirtdress
Make this pretty printed option feel prim and proper with ladylike heels and a chic bow tied at the neck, or rough it up by wearing it open over a blouse and leather leggings.
To buy: $148; bananarepublic.com.
Lands’ End Women’s Plus Twist Neck A-Line Dress
With soft fabric that drapes in all the right places, an adjustable belt for the perfect fit, and an elevated, twist detail at the neck, this berry-hued dress will be on repeat all season long. Also available in cobalt blue.
To buy: $89; landsend.com.
& Other Stories Floral Print Maxi Dress
Hitting just above the ankles, this statement print dress is an instant outfit that requires only the most minimal of accessories to get you out the door.
To buy: $145; stories.com.