The Most Comfortable Everyday Dresses for Work or Play (2024)

Sure, a bold print and body-skimming silhouette might not scream comfort—until, that is, you find out that it's made from stretchy jersey.

Simple and perfect, the T-shirt dress will always serve you well. This, by Smash +Tess, is cut to hit at *just* the right spot in your leg, and isn't too wide, so you'll feel sleek even though you won't feel constricted at all.

If you are looking for something of the cozier variety, Boden added puff sleeves to their sweatshirt dress for a fashionable twist on a comfy fave.

Who said comfortable had to mean casual? I dream of being the woman who lounges around the house in a silk dress, like Elizabeth Taylor would, Iimagine. But for more formal affairs where I have to be polished, Refine's ultra-sexy slip dress with a flattering drape is on my must-have list.

Last summer I saw someone on Instagram wearing this maxi-dress in bright yellow and never have I regretted not buying a piece more in my life. It's loose, but silhouette grazing and the kind of piece you can dress up with a few choice accessories.

For those who gravitate towards a more fitted option, Staud's pink and orange knit cardigan dress is sultry with a touch of whimsy, without any constricting tailoring.

A loose swing dress is my go-to in the summer months for good reason: breathable with just a suggestion of girlishness.

Who amongst us hasn't fallen in love with Splendid's sinfully soft t-shirts? Here, you get that goodness in dress form.

We could all do with one—or several—easy, flouncy dresses in our wardrobes. This one's navy hue is great for spring, but you could just as easily throw on tights and wear it in the fall too.

LoveShackFancy is practically synonymous with blousy, ruffly goodness and just because this dress is a mini does not make it any less forgiving. I plan to wear it the minute temperatures reach 80.

The elegance of the ruffles on this dress, paired with the body-friendly smocking, isn't just flattering, it's damn comfortable too.

A frilly and forgiving take on the denim dress. Slightly peasanty, very cool, and perfect for pairing with everything from spring sandals to fall boots.

This season, I'm getting back into the empire waist—maybe because of all of that Bridgerton binging I did this winter. Ciao Lucia's crisp cotton dresses are some of my favorites, and the subtly sexy double tie at this top takes this dress to a place that's so far from matronly, it's hard to describe. I look forward to swanning about in this dress multiple days a week because Iam who Iam.

A vintage-style floral maxi is just the romantic ticket. Plus, you can cinch the waist slightly depending on your vibe—and add heels for a polished look in the snap of your fingers!