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21 Maxi Dresses to Slip Into this Fall

When you need a break from jeans.

maxi dresses
Design by Morgan McMullen

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 gift: I've done the homework for you. (This may seem a little premature given it's still summer, but it's best to be prepared.) The 21 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 (with a mask on), soaking up the summer rays.


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The Check Print Dress
Checkered Long Shirt Dress
Ganni farfetch.com

Everyone needs a practical check print shirt dress in their closet. This one from Ganni has easy button fastening on the front and a loose fit, so you can pair it with jeans underneath if you wish. You can also leave buttons undone at the bottom to give it a DIY slit detail. 

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The Belted Dress
Belted Button-Up Maxi Dress
Dodo Bar Or farfetch.com

Go for rich browns and reds to celebrate the fall season. This button-up maxi dress falls into that category and has pretty gold buttons and a front button fastening. Style with a pair of black boots and a trench coat.

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The Turtleneck Dress
Kamali Kulture Go Turtleneck Maxi Dress
Norma Kamali shopbop.com

Fall is the start of turtleneck season and I'm all for it. First up on my list of what I'd want to wear: This simple, slinky black jersey. You can make it feel more fitted with a belt or edgier with a corset. Accessories with color will jazz up the dark hue. 

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The Vichy Pattern Dress
Vichy Pattern Long Dress
Fendi farfetch.com

A silk dress that's sophisticated enough to wear for your most buttoned-up occasions, but also laidback enough to pack for a trip to the countryside. All you need to top off this look is a hat.

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The Feather Shirt Dress
Mandevo Shirt Dress
Taibo Bacar industrieafrica.com

For a shirt dress that has it all, from faux feathers to crystals, direct your attention to this option from Mozambican brand Taico Bacar. The silk sateen is made by local communities in Mozambique for a unique artisan spin. This is a one-of-a-kind piece you won't find at your nearest retailer. 

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The Chiffon Dress
Chiffon Dress
H&M hm.com

Chiffon dresses are warm, lightweight, and look great when worn with slouchy boots underneath. This under $50 option has billowy balloon sleeves, a detachable liner, and adjustable shoulder straps so you're in charge of how much skin you want to show.

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The Square Neckline Dress
Madison Long Sleeve Maxi Dress
Lost + Wander nordstrom.com

For those who are not ready to give up their bright summer floral frocks, here's a printed one with sleeves that feels fall appropriate. The ditsy print is playful and romantic while the ruffles at the waist feel feminine. Meanwhile, gathered sleeves will it a retro-inspired look. 

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The Animal Motif Dress
Printed Silk-Twill Maxi Dress
Gucci net-a-porter.com

Tired of florals and stripes? Then how about this very, very bold animal motif dress? The "feline garden" pattern features leopards and tigers hiding in long blades of grass. Pounce on this maxi now before it's sold out and wear with a denim jacket or a black leather moto outerwear. 

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The Bridal-Ready Dress
Sienna White Ruffle Neck Silk Maxi Dress

Brides of 2021 (and 2022), this is your under $500 wedding dress that looks gorgeous for both the ceremony and reception. It's made from 100 percent silk and has a layered neckline, which gives it a vintage '30s touch. Best of all, this dress can easily be re-worn for other formal events. 

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The Floral Dress
Ava Tiered Floral Fil Coupé Gown
Erdem matchesfashion.com

We can picture this dress on Kate Middleton, who often wears the brand. If you're obsessed with her style or want to channel those royal vibes, slip into this white fil coupé gown. The sleeveless style will show off your arms while the floor-sweeping hem allows you to conceal a more comfortable, though not always "cute," pair of shoes. 

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The Evening Gown
Bow-Detailed Halterneck Cady Gown
Christopher John Rogers net-a-porter.com
$365.00 (33% off)

My favorite part about this dress is the open back where the halter neck ties come together to form a large bow. Talk about drama. This emerald evening gown is your go-to for a show-stopping look at your next fancy event. 

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The Denim Dress
Cedar Dress
Rachel Comey shopbop.com

When fall hits, you can get away with wearing heavier fabrics like a denim dress (I would be sweating in this in 90-degree summer heat). This pull-over indigo maxi can be paired with just about any autumn shoe, from a sophisticated boot to your scuffed up sneakers.

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The Zebra Stripe Dress
Milia Seebra Dress
AllSaints us.allsaints.com

It can be nice to break up your all-black uniform with a print like this zebra striped dress. The colors are still dark and muted enough to wear with your favorite black booties and will help you make a statement where ever you go.

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The Neutral Color Dress
Millie Belted Linen-Blend Maxi Shirt Dress
Staud net-a-porter.com
$177.00 (40% off)

You're ready to stash away your summer florals in favor of neutrals come fall/winter. This beige shirt dress will work nicely into your wardrobe because of its timeless silhouette. The dress is made from a mid-weight linen blend, so it'll be suitable for that unpredictable in-between seasons weather. If you feel chilly in the mornings, just drape a jacket over your shoulders. 

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The Bold Dress
Cotton Voile Maxi Dress With Side Cutouts
New York and Company nyandcompany.com

For a dress that's full of life and personality, scoop up this Gabrielle Union design. The prints were inspired by the culture and art/music of Little Haiti, Miami, which is why the details feels so vibrant and fun. Style with your favorite pair of leather knee-high boots.

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The Stripe Dress
Multi Striped Tiered Maxi Slip
Hope for Flowers hopeforflowers.com

This maxi will come in handy for mornings when you're already running 10 minutes behind schedule. Just throw on some earrings and let the stripe dress do its thing. The silhouette alone already makes a stylish statement. To stay warm once the crisp air rolls in, layer a tee or turtleneck underneath.

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The Vacation Dress
Awa Kimono Joal
Diarrablu diarrablu.com

This dress is handmade in Dakar, Senegal, so the length can be customized according to your height. Pack this with you on your next vacation. It's the perfect travel dress because of the photogenic print and ease of wear. 

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The Wedding Guest Dress
Maxi Dress With Bat Wing Sleeves
ASOS Design us.asos.com

When you don't know what to wear to those fall weddings, this dress will come to the rescue. The mustard color is similar to that found in fall foliage while the built-in sash will cinch in your waist to show off your curves. 

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The Plunging Neckline Shirt Dress
Eva Shirt Dress
Free People freepeople.com

This shirt dress has some sexy elements like the plunging neckline and side slits to make it look less buttoned-up than other options on the market. Throw on the dress with a pair of sneakers or sandals and call it a day—it's that easy to wear.

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The 1930s-Inspired Maxi
Zhandra Floral Midi Dress
RIXO net-a-porter.com
$264.00 (40% off)

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.   

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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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