Get a Head Start on Transitional Dressing With These Breezy Maxi Dresses

Maxi dresses are the answer to all your late summer and early fall fashion woes.

Get a Head Start on Transitional Dressing With These Breezy Maxi Dresses
Maxi dresses are the solution to all your transitional dressing woes. Grace Kamin for Observer

Summer’s not over yet, but as temperatures start to oh-so-subtly drop and you reach for that lightweight sweater on breezy nights, it’s time to start thinking about your transitional wardrobe. That tricky period at the end of summer and early fall is always hard to dress for, but when in doubt, you can’t go wrong with a classic maxi dress.

While linen frocks, caftans and flirty minis are perfect for peak summer times, the maxi dress is ideal for both hot summer days and brisker fall moments; 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, heading to get your pumpkin spice latte or 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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  • La Ligne.

    La Ligne Claire Dress

    We love a good smocked dress, and this ruffled navy cotton frock seamlessly brings that look into fall, thanks to the darker colorway and short sleeves. While it does technically fall a touch above the ankle, it’s perfect for those days you simply cannot handle a hem dragging on the floor.

    $395, Shop Now
  • Smash + Tess

    Smash + Tess River Maxi Dress in Midnight Black

    You can’t go wrong with a breezy, black tank maxi dress. This one has a comfy, relaxed silhouette, too.

    $65, Shop Now
  • Splendid.

    Splendid McCall Sweater Dress

    It’s been a minute since we’ve looked at a sweater dress (it’s been a ridiculously hot summer), but this tank-style dress has us ready to throw on a knit frock. This ribbed maxi works for warm and cool weather, and is a great option that takes you from the office to a night on the town.

    $168, Shop Now
  • Rails.

    Rails Lucille Cotton Maxi Dress

    This crisp, cotton spaghetti-strap maxi is the perfect fabrication and silhouette for summertime, while the earth tones and longer length easily transition to autumn.

    $228, Shop Now
  • Staud.

    Staud Faye Maxi Dress

    No wardrobe is complete without a breezy black maxi, and this short-sleeved Staud dress is sure to be a staple for years to come. Drawstring bows at the sleeves and a ruched bodice add structure, but in a comfy and effortless way.

    $345, Shop Now
  • Farm Rio.

    Farm Rio Mixed Tapestry Scarf Maxi Dress

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

    $330, Shop Now
  • L'Agence.

    L'Agence Stefani Dress

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

    $420, Shop Now
  • Ba&sh.

    Bash Kezia Dress

    Embrace the ’70s sartorial moment in this flowy, tie-dye print maxi.

    $450, Shop Now
  • Matteau.

    Matteau + Net Sustain Tiered Maxi Dress

    This chic shirred maxi is at the top of our current add-to-cart list; it has delicate spaghetti straps and subtle deep v-neck, and we love the way it flows out at the bottom. The cotton material and feminine details are so pretty for summer, while the earth tone colorway easily transitions to autumn; throw on a leather jacket and boots and you’re all set.

    $560, Shop Now
  • PatBo.

    PatBo Long Sleeve Knit Maxi Dress

    Don’t be afraid to make a more daring fashion choice this season and try out more unexpected silhouettes, like this long-sleeved maxi with strategically placed cutouts.

    $675, Shop Now
  • Mirth.

    Mirth Rio Dress

    This effortless frock dress is equal parts whimsical and put-together.

    $310, Shop Now
  • Faherty.

    Faherty Susanna Smocked Dress

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

    $248, Shop Now
  • Cleobella.

    Cleobella Margot Ankle Dress

    If you’re looking for a dressier option, consider this elegant black halter neck maxi.

    $258, Shop Now
  • Ciao Lucia.

    Ciao Lucia Pirro Dress in Cream

    As the seasons start to change, swap out your blinding summer whites for softer creams, like this dreamy cotton poplin frock from Ciao Lucia. Yes, it does hit a bit above the ankle, but it’s just such a good dress that you can wear any time of the year, and we’re *obsessed* with the black bows.

    $435, Shop Now
  • Reformation.

    Reformation Nira Dress

    Reformation is a go-to for summer dresses, but the sustainably-focused brand also has plenty of chic transitional frocks, like this red floral number.

    $248, Shop Now
Get a Head Start on Transitional Dressing With These Breezy Maxi Dresses