The Chic Maxi Dresses That Make Transitional Fashion a Breeze

'Tis the season of the long, flowy dress.

The Chic Maxi Dresses That Make Transitional Fashion a Breeze
collage of four maxi dresses
Maxi dresses are the key to transitional dressing.

When it comes to transitional dressing, you’ll be hard-pressed to find an item of clothing better equipped for the situation than a maxi dress. It’s not always easy figuring out what to wear during these in-between months, but you simply can’t go wrong with a classic maxi. These long frocks are ideal for steamy summer days, crisp springtime moments, brisk fall moments and everything in between; it’s all about how you style the look.

You can accessorize with a leather jacket and ankle boots when it’s cooler out, or pair it with sandals and a straw bag, depending on the weather. When it comes to transitional dressing, a maxi dress is a true powerhouse, and we especially love that the sartorial staple is one of those pieces that you can seamlessly dress up or down, which is a key component of any item in a quality capsule wardrobe. There are casual daytime maxis and dressier long frocks, all of which you’ll find yourself turning to year after year.

Whether you’re attending a summertime cocktail fête, getting dressed for a day of errands, heading out with friends or just struggling over how to clothe yourself for that return to the office, there’s a maxi dress that’s perfect for the occasion. Below, see the best maxi dresses to shop now that make transitional dressing an absolute breeze.

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The Best Stylish Maxi Dresses to Shop Now

  • La Ligne Mary Alice Ruched Long Sleeve Tiered Maxi Dress
    La Ligne Mary Alice Ruched Long Sleeve Tiered Maxi Dress

    La Ligne Mary Alice Ruched Long Sleeve Tiered Maxi Dress

    We love a good smocked dress, like this ruffled black long-sleeve number that’s sure to be on repeat in your transitional season wardrobe. The fitted bodice seamlessly flows out into a tiered skirt, for a flattering and versatile look.

    $495, Shop Now
  • sleeveless ruffled blue and pink floral maxi dress with v-neckline

    Saloni Rita Ruffled Floral-Print Silk-Voile Maxi Dress

    This pretty floral maxi dress is everything you’d want from a silky frock; you can wear it more casually or as a special occasion ensemble (it’s wedding guest season, after all), depending on how you accessorize. The blue and red print on this ruffle maxi dress is a more unexpected color scheme than the traditional pink florals, for a fun twist on the look.

    $865, Shop Now
  • mango long sleeve knit dress

    Mango Knitted Dress

    A long-sleeved knit maxi is a minimalist dressing powerhouse.

    $99.99, Shop Now
  • short sleeve baby blue belted pleated maxi dress
    Self Portrait.

    Self Portrait Chiffon Maxi Dress

    While a shapeless floor-length frocks can look more casual, unflattering and even a touch sloppy, there’s no chance of that with this elegant sky blue chiffon short-sleeve maxi dress. The ladylike silhouette, complete with lace accents on the sleeves and neckline, is perfection, and the belted waist adds structure to the pleated skirt. You can dress this up with strappy sandals and a clutch for evening, or wear it with flats during the day.

    $615, Shop Now
  • Rails.

    Rails Lucille Cotton Maxi Dress

    This crisp, cotton spaghetti-strap maxi is the perfect fabrication and silhouette for warm days, while the earth tones and longer length ensure it’s just as appropriate for spring and autumn.

    $228, Shop Now
  • Ba&sh Cecilia Floral Tiered Maxi Dress
    Ba&sh Cecilia Floral Tiered Maxi Dress

    Ba&sh Cecilia Floral Tiered Maxi Dress

    No wardrobe is complete without a breezy floral maxi, like this adorable purple dress from Ba&sh, complete with feminine short flutter sleeves and a flattering belted waist.

    $595, Shop Now
  • Farm Rio.

    Farm Rio Mixed Tapestry Scarf Maxi Dress

    Try out a more bohemian vibe in this flowy printed long-sleeve maxi dress, which has plenty of tassels and ruffles, as well as the prettiest tiered skirt.

    $330, Shop Now
  • navy spaghetti strap maxi dress

    L'Agence Stefani Dress

    This flowing navy v-neck maxi dress hits all the right marks for either a fancy affair or a casual day out; put on a pair of heels for a more elegant fête, or accessorize with flats or sandals and keep it more low-key.

    $420, Shop Now
  • Zimmermann Cira Tiered Cotton Tie-Waist Shirtdress

    Zimmermann Cira Tiered Cotton Tie-Waist Shirtdress

    Lean into the spring atmosphere with this long-sleeve floral maxi, which has a high stand collar and a removable beaded belt.

    $950, Shop Now
  • strapless shirred tiered olive green maxi dress

    Matteau Shirred Silk Tiered Maxi Dress

    This chic shirred maxi is at the top of our current add-to-cart list. You can wear it either strapless or with the thin spaghetti straps as a halter neck, and the olive green hue is perfect for transitional times of year.

    $1,290, Shop Now
  • cream sleeveless knit maxi dress

    Courrèges Ribbed-Knit Maxi Dress

    Of course cool girl French brand Courrèges is behind the ultimate knit maxi dress. This cream-colored sleeveless frock has a subtle cutout at the high neckline and an elevated bodycon silhouette—it’s a lesson in perfecting minimalism.

    $675, Shop Now
  • Mirth.

    Mirth Rio Dress

    This effortless tiered maxi dress  is equal parts whimsical and put-together, with a square neck and charming bow straps.

    $310, Shop Now
  • Faherty.

    Faherty Susanna Smocked Dress

    Go all in on the prairie dress aesthetic with this long-sleeved smocked maxi.

    $129, Shop Now
  • Bytimo Floral Print Georgette Maxi Dress

    Bytimo Floral Print Georgette Maxi Dress

    Embrace a full cottagecore vibes in this lovely floral puff-sleeve frock, which has a flowy skirt and cinched smocked waist. The three quarter sleeve length is perfect for when you want more coverage on your arms without going full long-sleeves, for a chic garden party aesthetic.

    $514, Shop Now
  • Agua by Agua Bendita Espliego Oasis Maxi Dress
    Agua by Agua Bendita.

    Agua by Agua Bendita Espliego Oasis Maxi Dress

    Instead of the usual long-sleeve or tank iterations, consider a romantic floral off-the-shoulder maxi dress, like this gorgeous frock from Agua by Agua Bendita.

    $780, Shop Now
  • Poupette St Barth Denise Printed Satin Maxi Dress
    Poupette St Barth.

    Poupette St. Barth Denise Printed Satin Maxi Dress

    While Poupette is perhaps most closely associated with their chic beachwear, the brand also has plenty of pieces that are just as suitable for everyday or an evening out, even if you’re not on a beachy getaway. This delicate A-line spaghetti strap dress has a wide v-neck and flowing tassels, for a breezy, effortless feel.

    $450, Shop Now
  • camel colored long slip tank dress

    Skims Soft Lounge Ribbed Long Slipdress

    Kim Kardashian’s Skims is known for their flattering shapewear, but the brand also makes great everyday staple looks, like this body-hugging, lightweight slip dress. It’s no surprise the versatile frock is a best-seller for the brand, and it’s also plus size-inclusive, with a range from XXS to 4X.

    $78, Shop Now
  • Reformation Annabelle Silk Dress

    Reformation Annabelle Silk Dress

    Reformation is a go-to for everyday spring and summer dresses, but the sustainably-focused brand also offers plenty of dressier frocks and cocktail dresses for special occasions, like this sleek gown, with a subtle cowl scoop neck.

    $448, Shop Now
  • sleeveless floral print maxi dress

    Mirth Biarritz Dress in Rose Bloom

    This sleeveless floral print maxi has a relaxed but flattering silhouette, with a v-neckline and subtle cutouts around the bodice. It’s so versatile and easy to throw on; wear it as a breezy sundress during warmer months, or add a denim jacket or leather topper when it’s cooler out.

    $340, Shop Now
The Chic Maxi Dresses That Make Transitional Fashion a Breeze