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15 Best Maxi Dresses to Slip Into this Fall

Style them with leather ankle boots or chunky sneakers.

New York Fashion Week - Street Style - Day 1
Christian VierigGetty Images

For some, fall weather means the return of cardigans and denim jackets. For me, it means knitted sweater dresses and long-sleeve maxis I can wear with boots. The new season offers hundreds, if not thousands of maxi dress styles, so where does one even begin to shop? Before you browse through 30 pages of dresses from your favorite retailers, here's a present: I've done the homework for you. The 15 maxi dresses ahead will have you covered for all facets of your life—work, brunch, parties, pumpkin patches, apple picking.... So shop away and spend that extra time you now have outdoors, soaking up the last bits of summer.

1 of 15
The 1930s-Inspired Maxi
Zhandra Floral Midi Dress
RIXO net-a-porter.com

One of the most versatile dresses for fall is this floral-print silk crepe de chine maxi from RIXO. You can wear with heels to that Saturday wedding and with flats for work Monday morning. The piece has a pretty twisted front detail and fluttery sleeves that were inspired by styles from the '30s.   

2 of 15
The Butterfly Print Maxi
Long Floaty Dress With Butterflies Print
Sandro sandro-paris.com

This dress, with its warm gold and brown tones, reflect the colors of fall foliage. Though butterflies may not be bountiful at this time of the year, they will forever be immortalized in the print of the dress. The style also appeals to more boho than overly sweet senses thanks to the long puff sleeves and lace trim on the chest.

3 of 15
The Blush Pink Maxi
Wrap Dress
H&M hm.com

You're looking for an affordable blush dress all your bridesmaids can wear: here it is. The flattering wrap design and tiered sleeves will make anyone feel comfortable once they slip the dress on. Your bridesmaids can even rewear this again for all their other weddings.

4 of 15
The Puff Sleeve Maxi
Sante Silk Maxi Dress
The Row net-a-porter.com

Net-a-Porter's exclusive capsule collection with The Row offers the most beautiful chambray blue mélange hue I've ever seen. The cool tone is both calming and soothing while the dress itself falls artfully over the body. Don't miss the important details like the gathered shoulders and sleeve cuffs. 

5 of 15
The Polka Dot Maxi
Long Printed Dress
Zara zara.com

If this dress doesn't immediately remind you of something Kate Middleton would wear, please study all her past looks. (Okay, I know I'm a little obsessed.) The modesty in the garment is offset by the vibrant green and white print, which makes the maxi all the more bold and daring to wear.

6 of 15
The Prairie-Like Maxi
Liliana Grid-Print Cotton Maxi Dress
Mara Hoffman modaoperandi.com

Choose a lightweight cotton dress to transition from summer into fall. Once the weather gets colder, you can layer on a coat and wear with flats or western-inspired boots. The long blouson sleeves give off Little House on the Prairie vibes, which I honestly don't mind. 

7 of 15
The Toss-on-and-Go Maxi
Printed Long Dress
Mango mango.com

This maxi will come in handy for mornings when you're already running 10 minutes behind schedule. Just throw on some earrings voluminous floral and stripe dress do its thing. The silhouette alone already makes a stylish statement. 

8 of 15
The Vacation Maxi
Tassel Tie Maxi Dress
Dolan nordstrom.com

This is the kind of dress I would pack for seaside vacations in Italy or for wandering around in at Turkish markets or artisan fleas in Mexico City. Basically, this is the perfect travel dress because of the photogenic color, print, and tassels. Pair with sandals, or sneakers if you want more comfort.

9 of 15
The Layerable Maxi
Kendall Bow-Tie Detailed Floral-Print Silk Dress
LoveShackFancy modaoperandi.com

This LoveShackFancy is too pretty to wear only one season a year so extend its closet life by layering a long-sleeve tee or a turtleneck top underneath when it gets cold. Instead of sandals, give it the athelsiure touch with a pair of sporty or chunky sneakers.

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The Maxi for the Bride
Garland Marie Ruffled Tulle Gown
Needle & Thread modaoperandi.com

Brides, I've found the most romantic multi-tier dress you can wear for your reception dinner or bridal shower in the fall. Unlike the brighter florals of summer, this maxi contains more muted pinks and greens for a softer tone. The black lace trims add structure and highlights your frame, so you don't drown in fabric.

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The Size-Inclusive Maxi
Stripe Short Sleeve Maxi Dress
City Chic nordstrom.com

Tired of florals? Then how about stripes? This watercolor brushstroke maxi will look great under a denim jacket or black leather moto outerwear—your go-to's for autumn weather. The best part about this dress is that it's size inclusive, ranging from extra small to double XL. 

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The Dark Floral Maxi
Floral Print Ruffle Wrap Dress
Michael Kors nordstrom.com

Let your black leather knee-high boots peek out from underneath the flouncy skirt of this Michael Kors dress. It's an unexpected pairing for most, but if you've been watching the runways then you know this is the combo to try for the season.

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The Vegan Leather Maxi
Rosana Vegan Leather Button-Front Dress
Nanushka modaoperandi.com

I've had my eye on investing in a vegan leather piece from Nanushka and this dress is calling my name. The material is buttery soft and smooth, so it comfortably lays on your body. It also comes with functional buttons in the front and a detachable waist belt to enhance your frame.

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The Simple Maxi
Tie Back Wrap Maxi Dress
ASTR the Label astrthelabel.com

When you don't know what to wear to those fall weddings, this dress will come to the rescue. The floral print in a neutral color is perfect for autumn as you kiss goodbye your summer brights. Wear with wedges for the wedding or sneakers when you want to look more casual.

15 of 15
The Maxi Slip
Black Silk Dress
Silk Laundry

Kate Moss' '90s slip dress was iconic (and very sheer). If you're feeling nostalgic for that era, scoop up this long, slinky dress from Silk Laundry. The garment dips low in the back—and front—for added sex appeal. Slip on casual sandals and top with an extra-long cardigan for those late summer/early fall beachside bonfires.


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