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.

Subscribe to Observer’s Lifestyle Newsletter

All products featured are independently selected by Observer editors. When you buy something through our links, we may earn an affiliate commission that supports our work.

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.

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

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.

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.

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.

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.

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.

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

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.

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.

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

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

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

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.

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.

We get it: you like to have control of your own internet experience. But advertising revenue helps support our journalism. To read our full stories, please turn off your ad blocker. We'd really appreciate it.

Below are steps you can take in order to whitelist Observer.com on your browser:

Click the AdBlock button on your browser and select Don't run on pages on this domain.

Click the AdBlock Plus button on your browser and select Enabled on this site.

Click the AdBlock Plus button on your browser and select Disable on Observer.com.