27 Dresses That Look Cute But, More Importantly, Comfortable

27 Dresses That Look Cute But, More Importantly, Comfortable

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A velvety maxi you can belt or leave loose for that coveted shapeless silhouette.


You can get a belt like the one in the picture right here.

Promising review: “This dress is gorgeous! I have received tons of compliments from random strangers, and I’ve only worn it about three times. It’s ridiculously comfortable and the pockets are excellent. I mean, pockets in a dress are one of the greatest things ever, but I feel like most of the time I can’t actually use them. It creates an unsightly bulge. That is not the case with this dress. Because it’s so open and flowy, I can stash a chapstick or a pen in the pockets without it showing at all. The color is also true to the Amazon photo, though of course, depending on lighting, sometimes it looks more golden yellow and other times more orange. Either way, it’s going to be perfect for fall.” —Jessica

Get it from Amazon for $19.99+ (available in sizes XS–L and four colors).


A hi-low number you’ll be plaid to have.


Promising review: “This dress is amazing. I got lots and lots of love and compliments. It was very comfortable. I actually ordered another one in white, and I plan to reorder in blue and green.” —Dee Kinu

Get it from Amazon for $26.99 (available in sizes S–XXL and eight colors).


An apron midi dress for anyone who wants to look farmer chic.

Urban Outfitters

Get it from Urban Outfitters for $79 (available in sizes XS–XL).


A cowl neck dress in a nice mauve rose color to help grow your wardrobe.


Get it from Loft for $79.99 (available in sizes 14–26).


A button-adorned midi dress with — *drumroll* — pockets!


Promising review: “This is SO CUTE. The length is perfect, the buttons are perfect, it’s a nice substantial material without being heavy, IT HAS POCKETS… Seriously, buy this dress!” —Nicola Griffin

Get it from Amazon for $16.99+ (available in sizes S–XXL and nine colors; available in long or short sleeves).


A cutie pie T-shirt dress simple enough to wear with all your best accessories.


Promising review: “I love this dress! It’s perfect for date night! It fits like a dream! It didn’t cling to anything I didn’t want it to. It’s so soft! I will be ordering in other colors!” —Morgan Hargrove

Get it from Amazon for $5.79+ (available in sizes S–3XL and 14 colors; available with long or short sleeves).


A shift dress sure to make you look as cute as a button.


Promising review: “I wasn’t expecting too much from this since my two previous clothing purchases were a bit of a let down. But not this! It fit perfect, it was soft, and thick. No need for a cami under this! I want to buy one in every color! I wore it to work today and it was super comfortable.” —Randall McCormick

Get it from Amazon for $13.99+ (available in sizes S–XXL and 18 colors).


An oversized sweater dress for next-level snuggliness that could rival that of a teddy bear.


Promising review: “I absolutely love it. It’s so cute and cozy. I’m definitely planning on ordering again. <3" —JJ

Get it from Amazon for $33.99+ (available in sizes S–XL and five colors).


A faux collar shift dress that may very well be the perfect solution to the age old question: “what should I wear?”


Get it from Amazon for $15.99+ (available in sizes XS–3XL and five colors).


A chic sweater dress with a diagonal line of buttons to give it a little extra charm.


Get it from Amazon for $26.75+ (available in sizes 1X–4X and three colors).


Promising review: “Buy this right now! You can rock it with ankle booties or over the knee boots, and it’s so adorable! I’ve also styled it with a fur vest which was super cute. I definitely recommend this particular brand too because the fabric isn’t T-shirt fabric.” —SparklySprinkles

Get it from Amazon for $18.59+ (available in sizes S–XXL and 30 colors).


A popular sleeveless option pretty much made for lounging in (and looking damn fine doing it).


This dress has over 1,600 positive reviews!

Promising review: “Love this dress. It even has pockets!! I will be buying another. The fabric is soft and comfortable, and the fit was perfect. Very flattering and doesn’t show too much thigh.” —Amazon Customer

Get it from Amazon for $14.99+ (available in sizes S–XXL and 15 colors).


A ribbed shirt dress that I seriously can’t stop admiring.


Get it from Boohoo for $12 (available in sizes 12–24 and three colors).

amazon.com, amazon.com

Promising review: “I absolutely love this!!!!!!!! Great quality!! I love big sweaters and that is exactly what I got! Really big and long. And very thick for cold weather!” —Reader

Get it from Amazon for $35.99 (available in sizes S–3XL and nine colors).


An easy-breezy swing dress with cut-out shoulders for people who are more than ready for spring.


Promising review: “Excellent purchase. I loved the dress. It came to just above my knees and when paired with a sweater, it was appropriate for work. I have not washed this dress yet, but the quality of the fabric was nice. Not too heavy, but definitely not light.” —K isfor Kandace

Get it from Amazon for $15.99+ (available in sizes 14–26 and 28 colors and patterns).

amazon.com, amazon.com

Promising review: “This is the dress if you’re looking for comfort! The fabric is pretty soft and breezy! It’s perfect for a summer/fall weather! I’m very happy with this purchase!” —Jess Palacios

Get it from Amazon for $22.98 (available in sizes S–XXL and 14 patterns).


A polka-dotted sweetie to really round out your wardrobe.


Promising review: “This dress is so cute and comfortable! Love the pockets and the higher neckline (so no need to layer a cami). I am 5’2″ and the dress hits about three inches below the knee, which is great. The elastic waist is comfortable and not too tight. Wonderful dress for the money!” —JH

Get it from Amazon for $16.99+ (available in sizes S–XL and three colors).


A leopard smock dress that looks so cozy, you should pounce on it immediately.


Get it from Boohoo for $14.80 (available in sizes 12–24).


A skater dress dotted in faux pearls that’s ~pearl~fect for winter.

amazon.com, Amazon

Promising review: “Super cute dress that is a little short for my curvy body. I did wear it with black shorts underneath and felt completely comfortable. I love the style with the black with white pearls on top. It looks very chic.” —kevinerhard

Get it from Amazon for $19.99 (available in sizes XS–L and three colors).


A long-sleeved midi dress that miiiiiight look good on everyone. You should probably get one for everyone you know just to make sure.


Promising review: “I absolutely love this dress! I ordered it in black and it arrived quickly, fits perfectly, and is both comfortable and flattering. The fabric is soft and lovely and the extra bonus is that it has pockets. I will soon order another in a different color!” —TAMARA WATSON

Get it from Amazon for $15.99+ (available in sizes S–2XL and 13 colors).


A raw edged V-neck for a casual and capacious look.


Get it from Asos for $24 (available in sizes 12–24).

amazon.com, amazon.com

Promising review: “The dress is super comfortable and very flattering! I received many compliments…which may have gone to my head just a little lol!” —Ella

Get it from Amazon for $18.89+ (available in sizes L–4X and 15 colors).


A lantern sleeve dress you’ll be drawn to like a moth to a flame.


Get it from Eloquii for $59.99+ (available in sizes 14–26 and two colors).


A mermaid bodycon that’ll go with swimmingly with the rest of your wardrobe.

Amazon, amazon.com

Promising review: “There are a lot of misses when it comes to Amazon clothes, but this was high quality, soft, not at all sheer, and looks great. I got a large so it didn’t look like cling film. Even with extra fabric, though, it’s very form fitting, so you better be fine with whatever bumps and lumps you may or may not have. Next paycheck, I’ll swing back and get a few more in different colors.” —Margaery Tyrell

Get it from Amazon for $26.99+ (available in sizes XS–XXL and eight colors).


And a collared denim mini so cute, you may forget all about your other clothes.

& Other Stories

Get it from & Other Stories for $89 (available in sizes 0–10).

Want more? Check out our favorite online clothing stores for all your shopping needs, perfect places to shop for clothes if you’re in your 30s, plus the best places to order custom t-shirts online and the best clothing stores for petite sizes. Still not satisfied? Check out all of our clothing content for even more.

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Reviews have been edited for length and/or clarity.

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