Kiyonna Barcelona Wrap Dress
A classic wrap style (updated with cute shoulder cut-outs) in versatile navy makes this dress a year-round staple. Add a blazer and tall boots for work during the winter months, then slip on sandals and statement earrings for warm-weather get-togethers.
To buy: $65; 6pm.com.
Ashley Stewart Pleated Tiered Maxi Dress
A tiered, pleated construction gives this maxi an ultra light and airy feel that can go casual with flat sandals or dressed up with heels (and eliminates any worry about clingy or tight-fitting fabric).
To buy: $49; ashleystewart.com.
ASOS Curve Smart Midi Dress
Office appropriate without feeling stuffy, this modest style transitions effortlessly from desk to dinner, no wardrobe change needed.
To buy: $64; asos.com.
Avenue Blue Mixed Floral Cold Shoulder Dress
There’s little not to love about a fit-and-flare frock. From the on-trend “cold shoulder” look to the leg-elongating asymmetric hem, this one will be on repeat for whatever your summer schedule throws at you.
To buy: $60; avenue.com.
City Chic Lace Underlay Chiffon Dress
A wardrobe not-so-secret weapon, every woman needs a go-to little black dress in her closet. With a lace pencil skirt and a floaty, sheer chiffon overlay, this one is anything but basic.
To buy: $89; bloomingdales.com.
Lauren Ralph Lauren Plus Denim Shirt Dress
Stock your closet with no-brainer summertime staples—like a denim dress—and you’ll never experience the “I have nothing to wear!” conundrum again. Just slip on your favorite shoes and you’re out the door.
To buy: $135; dillards.com.
Luxe by Carmen Marc Valvo Plus Size Floral Dress
This clever pattern centers the darkest part of the print right at your waist, creating a minimizing, nipped-in appearance that’s universally flattering.
To buy: $64; dressbarn.com.