20 Cute and Stylish Fall Dresses to Wear in 2020

Dress season isn't over yet.
fall dresses you'll see all over instagram

When you're envisioning the perfect fall wardrobe, dresses might not be part of your outfit formulas. In your head, fall is probably defined by leggings, trousers, and thigh-high boots to wear over your leggings and trousers. Because the more layers, the better. But you might be getting ahead of yourself. Here's why: Now that dressing for the outside world is being kept to a bare minimum, it's time to lean into cute and stylish fall dresses.

Also, 50-degree temperatures don't happen when the clock strikes midnight on September 22 — the colder temperatures creep up just like all that Zoom-homework you're leaving until the last minute while you're procrastinating reading this (it's our little secret, though). That's why you need to either not pack up your summer dresses just yet or invest in specific dress styles you can wear for the next three months (and even through winter if you get extra creative).

Want to know which dress styles we recommend for fall outfit equations? Scroll down to find out. From cozy (and trusty) ribbed knit dresses to fun cut-out dresses, we've rounded up cute and stylish fall dresses to wear inside (or out… momentarily). 

Ribbed Knit Dresses

With summer (almost) gone, we'll happily leave sweating in the past (at least, excessive sweating). So rejoice – you finally can wear your knits without the fear of losing your limbs! What's great about ribbed knit dresses is that even if you do wear them on a hotter day, you'll still get some breeze since they're a bit thinner compared to your oversized sweater dresses.

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Asos Design Curve Crew Neck Ribbed Midi Dress

Image may contain: Clothing, Sleeve, Apparel, Long Sleeve, Home Decor, Linen, Robe, Fashion, Dress, Overcoat, and Coat

Rib-knit Dress

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Simon Miller Rib Wells Dress

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Ava & Viv Long Sleeve Turtleneck Ribbed Sweater Dress

(Faux) Leather Dresses

Just like denim jackets and knit everything, once fall comes around, it's time to bust out your leathers. If leather blazers á la Kaia Gerber or long leather trench coats á la Matrix were the first pieces that came to mind, you're not wrong. This time around though, we're also stocking up on (faux) leather dresses. Just like their outwear counterparts, leather dresses will definitely make a statement with little to no effort.

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A-line Dress

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Faux-leather Shirt Dress

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Ganni Lamb Leather Dress

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Lantern Sleeve Faux Leather Dress

Shirt Dresses

Thanks to a handful of brands, this year-round staple item is getting a re-do for the fall season. From asymmetrical shirt dresses to colorful ones, make sure to add a few options alongside your classic, tailored white shirt dress!

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Kamila Wrap Shirt Dress

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Asymmetric Mini Shirt Dress

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The Parklet Shirtdress

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Pleated Cotton Shirt Dress

House Dresses

Alas, yes, many of the dress styles in this roundup will fall under this category. However, this fall we're saying, “it's not you, it's me,” to your typical fall hues and silhouettes and welcoming the most playful and fun midi dresses into our fall wardrobe.

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Asos Design Curve Shirred Tiered Maxi Dress

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Sleeper Loungewear Dress

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Wilfred Serenade Dress

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Skye Dress

Cutout Dresses

This summer cutout dresses were big. If you didn't get the change to experiment with them, don't fret because they're also here to stay for fall. It might be tricky to envision wearing them at first since they aren't exactly the most weather-ready trend but if paired with the right layers, prepare to rock some double-tap-worthy looks this season.

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Topshop Floral Cutout Midi Dress

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Ibiza Sun Dress Midi

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Long Sleeve Climber Dress

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Rotate Birger Christensen Kaya Cutout Mini Dress

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