13 Amazon Midi Dresses That Are Comfortable and Cute

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Whether I'm sitting in my home office or running errands, the staple I always rely on is a comfortable midi dress. It's one of those pieces that's so easy to wear with sneakers, plus I never feel restricted in it. Of everything in my closet, it's certainly the item you'll see me in the most. In fact, my sweatpants are starting to collect dust on my shelves simply because I much prefer the freedom (and effortless style) of a comfy midi dress.

With the leaves beginning to turn and the temperatures starting to cool down, I've been looking to update my midi dress collection with a few more fall-friendly styles that are equally trendy and ideal for wear during the transitional seasons. Naturally, I find that few retailers have a better or more affordable selection of styles than Amazon — so that's where I've started my shopping spree.

Already, I've discovered a wide variety of cozy, autumnal pieces that are perfect for the new season — and starting at just $27, too. From sweater midi dresses and ribbed midi dress styles to puff-sleeve frocks and more — if you're searching for a comfy piece that you can seamlessly wear for both work and weekends, let me be your guide. As a shopping editor, it's my job to uncover the designs customers are raving about — and Amazon has a lot to choose from. Read on to see what comfy midi dresses are worth your investment from Amazon, and buy something fresh for the fall.

— Additional reporting by Macy Williams

An Off-the-Shoulder Midi Dress: Find. Rib Jersey Off-Shoulder Midi Dress
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An Off-the-Shoulder Midi Dress: Find. Rib Jersey Off-Shoulder Midi Dress

We love a versatile dress as much as the next fashionista — which is probably why we're so obsessed with this chic Find. Rib Jersey Off-Shoulder Midi Dress ($26). The ribbed, off-the-shoulder style is breezy without being too casual — allowing you to easily dress the piece up or down, depending on the occasion. Plus, the body-hugging midi dress is also available to shop out in a black color.

A Pocketed Midi Dress: Amazon Essentials Midi Button-Front Tie Dress
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A Pocketed Midi Dress: Amazon Essentials Midi Button-Front Tie Dress

There's so much to love about this Amazon Essentials Midi Button-Front Tie Dress ($32), but the obvious appeal is in its pocketed design (pockets truly make everything better). With its wrap-tie feature, users can also adjust the comfy midi dress to carry a looser or tighter fit, as needed. Throw your favorite flats or mules on with the frock for a relaxed and stylish daytime look that you'll be wearing on repeat all.

A Wrap Midi Dress: Exlura Knit Sweater Wrap Dress
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A Wrap Midi Dress: Exlura Knit Sweater Wrap Dress

This Exlura Knit Sweater Wrap Dress ($47) is a best-seller for a reason. Sure, the cozy frock is available to shop in a wide variety of colors (though we're partial to this versatile beige color!). But the real appeal of the sweater dress is in its comfortable fit — provided by the style's soft nylon and acrylic composition that's as chic as it is cozy.

A Tank Midi Dress: Raikamitu Bodycon Tank Dress
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A Tank Midi Dress: Raikamitu Bodycon Tank Dress

Summer never has to end with this Raikamitu Bodycon Tank Dress ($30). The style is a warm weather essential that's breathable enough to be worn on even your busiest days outside of the house. Plus, it's also a staple for transitional weather — and can easily be layered with a distressed denim jacket or oversize blazer on top.

A T-Shirt Midi Dress: Amazon T-Shirt Flared Midi Dress
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A T-Shirt Midi Dress: Amazon T-Shirt Flared Midi Dress

Nothing says "comfy midi dress" quite like a T-shirt dress style. And contrary to popular belief, these frocks don't always have to be super muted or minimalistic — just look at this vibrant and patterned Amazon T-Shirt Flared Midi Dress ($27) for further proof. You'll make a serious statement on your next museum date or dinner party with this flared midi dress in tow.

A Formal Midi Dress: The Drop Ana Silky V-Neck Midi Slip Dress
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A Formal Midi Dress: The Drop Ana Silky V-Neck Midi Slip Dress

Layer a sweater over this influencer-favorite The Drop Ana Silky V-Neck Midi Slip Dress ($50) for a more robust (and cozy!) evening look. Whether you're heading out for date night, an evening event, or just a late night with the girls, this is the style you'll be reaching for time after time. Especially if you have the right heels to go with it!

A Sweater Midi Dress: Caracilia Crew Neck Midi Sweater Dress
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A Sweater Midi Dress: Caracilia Crew Neck Midi Sweater Dress

Cozy season and sweater dresses are truly synonymous with one another at this point. And we're more than ready to kick off the fall season on a stylish note with the help of this Caracilia Crew Neck Midi Sweater Dress ($30). The wrap-tie design guarantees a universally-flattering fit!

A Puff-Sleeve Midi Dress: Merokeety Plaid Smocked Dress
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A Puff-Sleeve Midi Dress: Merokeety Plaid Smocked Dress

Let the cottagecore vibes continue well into the fall with this Merokeety Plaid Smocked Dress ($33). The patterned gown features so many of our favorite style trends in one convenient piece, with the puff-sleeves, smocked design, and airy silhouette. Plus, it's also available in a bevy of other fall-friendly colors!

An Animal-Print Midi Dress: Kirundo Midi Leopard Dress
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An Animal-Print Midi Dress: Kirundo Midi Leopard Dress

You'll want to wear this Kirundo Midi Leopard Dress ($30, originally $38) all day, every day — and who can blame you? The fierce style plays perfectly into this season's animal-print trend, which is already making waves on the runway. And with its formal design, it can also double as the perfect dress to wear to the office or any other upscale event.

A Ribbed Midi Dress: Cable Stitch Stripe Ribbed Dress
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A Ribbed Midi Dress: Cable Stitch Stripe Ribbed Dress

Breezy summer dresses be damned — we're fully committed to cozy, ribbed styles this fall. This stretchy Cable Stitch Stripe Ribbed Dress ($70) has our full attention at the moment thanks to its bold, colorblock design and sexy silhouette. Reviewers hail the piece for its figure-flattering design that's still super breathable, too!

A Cozy Midi Dress: The Drop Suki Rib Midi Sweater Dress
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A Cozy Midi Dress: The Drop Suki Rib Midi Sweater Dress

Effortless elegance is embodied perfectly in this The Drop Suki Rib Midi Sweater Dress ($50). Your fall wardrobe deserves to have as many sweater dresses incorporated into it as possible, as this Amazon style feels like a great piece to start with. Bonus: it's also available in maroon and black colorways, so you can stock up on several great pieces in a single order!

A Floral Midi Dress: PrettyGarden Summer Wrap Dress
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A Floral Midi Dress: PrettyGarden Summer Wrap Dress

If we're being honest, there's never a wrong time to wear floral. And at the moment, we have our eyes on this PrettyGarden Summer Wrap Dress ($41) which feels like the most quintessential midi dress style for fall. A statement pair of nude heels will help take this autumnal ensemble to new heights.

A Jersey Midi Dress: Daily Ritual Jersey Midi Dress
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A Jersey Midi Dress: Daily Ritual Jersey Midi Dress

Turn heads in any room with the help of this Daily Ritual Jersey Midi Dress ($33). The breezy style is great for wear on those warmer fall days when you're not quite ready to commit to a sweater dress style. And with its sleeveless design, it's also super versatile for day-to-night wear, as it can be paired with a cozy knit cardigan or even a denim jacket.