Update Consent

Most Comfortable Midi Dresses From Old Navy

20 Comfy Old Navy Midi Dresses That'll Make You Forget Any Other Outfit Option

As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work.

If you think having a cosy, well-loved piece demands years of wash and wear, we found new clothing that'll completely change your mind. (And, if you don't, keep reading to learn about the items that need to be worked into your existing wardrobe stat.)

No, we're not talking about vintage t-shirts or super-soft sweatshirts, we're talking about medium-length dresses made of that same soft fabric. Opting for one of these lets you stay in your comfort zone — but with a style boost, too. Get absolutely giddy over an Old Navy midi and check out our top 20 picks to wear 24/7 ahead.

Image Source: Old Navy

Old Navy Sleeveless Waist-Defined Slub-Knit Midi Dress

We're starry-eyed over this golden Old Navy Sleeveless Waist-Defined Slub-Knit Midi Dress ($30-$35, originally $35), but the plum alternative has us hungry for more, too.

Image Source: oldnavy.gap.com
Old Navy Sleeveless Waist-Defined Slub-Knit Midi Dress
$30
from oldnavy.gap.com
Buy Now

Old Navy French-Terry Sweatshirt Midi Shift Dress

It truly doesn't get much more comfortable than this Old Navy French-Terry Sweatshirt Midi Shift Dress ($45) when lounging at home.

Image Source: oldnavy.gap.com
Old Navy French-Terry Sweatshirt Midi Shift Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Puff-Sleeve Clip-Dot Button-Front Midi Swing Dress

Both the black and berry Old Navy Puff-Sleeve Clip-Dot Button-Front Midi Swing Dress ($45) would look pretty matched with heels or strappy sandals for a dinner out.

Image Source: oldnavy.gap.com
Old Navy Puff-Sleeve Clip-Dot Button-Front Midi Swing Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Sleeveless Cross-Back Rib-Knit Midi Shift Dress

Give a cream ribbed midi a fall update with this Old Navy Sleeveless Cross-Back Rib-Knit Midi Shift Dress ($37, originally $40) in blue, butterscotch, or black.

Image Source: oldnavy.gap.com
Old Navy Sleeveless Cross-Back Rib-Knit Midi Shift Dress
$37
from oldnavy.gap.com
Buy Now

Watch This!

Pop Quiz

Watch the Cast of Fear Street Play a Creepy Game of Horror Movie "Would You Rather"

Old Navy Smocked Off-the-Shoulder Chambray Fit and Flare Midi Dress

While some denim can be stiff, the Old Navy Smocked Off-the-Shoulder Chambray Fit and Flare Midi Dress ($37, originally $40) is super-soft choice (and that smocked bodice may even tempt you to go bra-free).

Image Source: oldnavy.gap.com
Old Navy Smocked Off-the-Shoulder Chambray Fit and Flare Midi Dress
$37
from oldnavy.gap.com
Buy Now

Old Navy Fit and Flare Gingham Midi Cami Dress

We're so loving the pattern on this Old Navy Fit and Flare Gingham Midi Cami Dress ($40) as an alternative to all the floral picks out there — but, don't worry, this style does come that way, too.

Image Source: oldnavy.gap.com
Old Navy Fit and Flare Gingham Midi Cami Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Sleeveless Rib-Knit Linen-Blend Midi Shift Dress

This Old Navy Sleeveless Rib-Knit Linen-Blend Midi Shift Dress ($33, originally $35) looks so pretty with white high tops for fall (but the coral and baby blue hues do, too).

Image Source: oldnavy.gap.com
Old Navy Sleeveless Rib-Knit Linen-Blend Midi Shift Dress
$33
from oldnavy.gap.com
Buy Now

Old Navy Garment-Dyed Fit and Flare Slub-Knit Midi Dress

This Old Navy Garment-Dyed Fit and Flare Slub-Knit Midi Dress ($40) is so much more than a shapeless sheath for anyone who likes a bit of cinching at the waist (plus pockets and a pretty ruffle flair, too).

Image Source: oldnavy.gap.com
Old Navy Garment-Dyed Fit and Flare Slub-Knit Midi Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Floral Puff-Sleeve Button-Front Midi Swing Dress

The best part about both colours of this Old Navy Floral Puff-Sleeve Button-Front Midi Swing Dress ($45) is that there are hidden interior buttons so there's no gaping up top, no matter how you move.

Image Source: oldnavy.gap.com
Old Navy Floral Puff-Sleeve Button-Front Midi Swing Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Sleeveless Specially-Dyed Tie-Shoulder Cami Midi Swing Dress

Both the peach and sunny yellow Old Navy Sleeveless Specially-Dyed Tie-Shoulder Cami Midi Swing Dress ($22, originally $35) make solid choices as a beach coverup that you'll want to slip back on and wear out to dinner, too.

Image Source: oldnavy.gap.com
Old Navy Sleeveless Specially-Dyed Tie-Shoulder Cami Midi Swing Dress
$22
from oldnavy.gap.com
Buy Now

Old Navy Dobby Bell-Sleeve Midi Swing Dress

Swing into a new season with this Old Navy Dobby Bell-Sleeve Midi Swing Dress ($45) and sandals, slides, or sneakers.

Image Source: oldnavy.gap.com
Old Navy Dobby Bell-Sleeve Midi Swing Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Long-Sleeve Midi Sweatshirt Shift Dress

This cosy Old Navy Long-Sleeve Midi Sweatshirt Shift Dress ($45) comes in green or pink with pockets big enough to hold your phone . . . and the TV remote, too.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Midi Sweatshirt Shift Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Vintage Specially Dyed Sleeveless Midi T-Shirt Shift Dress

Much like your favourite tee shirt (but longer and sleeker), this Old Navy Vintage Specially Dyed Sleeveless Midi T-Shirt Shift Dress ($30-$35, originally $35) gets softer with every wear.

Image Source: oldnavy.gap.com
Old Navy Vintage Specially Dyed Sleeveless Midi T-Shirt Shift Dress
$30
from oldnavy.gap.com
Buy Now

Old Navy UltraLite Performance Racer-Back Ribbed Midi Dress

This Old Navy UltraLite Performance Racer-Back Ribbed Midi Dress ($30, originally $40) is more than just a casual dress as it's made from the same go-dry material as many of the workout clothes.

Image Source: oldnavy.gap.com
Old Navy UltraLite Performance Racer-Back Ribbed Midi Dress
$30
from oldnavy.gap.com
Buy Now

Old Navy Vintage Sleeveless Striped Midi Shift Dress

We'd pick either of these Old Navy Vintage Sleeveless Striped Midi Shift Dresses ($35) for a summer-to-fall transition piece as they both look cute solo or under a light jacket instead.

Image Source: oldnavy.gap.com
Old Navy Vintage Sleeveless Striped Midi Shift Dresses
$35
from oldnavy.gap.com
Buy Now

Old Navy Puff-Sleeve Tiered Striped Midi Swing Dress

Wear an Old Navy Puff-Sleeve Tiered Striped Midi Swing Dress ($45) for a full day out in the sun as it's swingy shape is perfect to go with the flow.

Image Source: oldnavy.gap.com
Old Navy Puff-Sleeve Tiered Striped Midi Swing Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Waist-Defined Striped Slub-Knit Cami Midi Dress

Switch up a solid for either Old Navy Waist-Defined Striped Slub-Knit Cami Midi Dress ($25-$33, originally $35) to wear now on its own, and later with a denim jacket on top or even a long-sleeved tee underneath.

Image Source: oldnavy.gap.com
Old Navy Waist-Defined Striped Slub-Knit Cami Midi Dress
$25
from oldnavy.gap.com
Buy Now

Old Navy Fit and Flare Short-Sleeve Tiered Midi Dress

Why not grab a charcoal Old Navy Fit and Flare Short-Sleeve Tiered Midi Dress ($40) for your go-to casual fall dress?

Image Source: oldnavy.gap.com
Old Navy Fit and Flare Short-Sleeve Tiered Midi Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Sleeveless Smocked Tie-Dye Midi Swing Dress

This flowing Old Navy Sleeveless Smocked Tie-Dye Midi Swing Dress ($40-$43, originally $50) is something to wear all day at home (whether working or relaxing), and out for errands, too.

Image Source: oldnavy.gap.com
Old Navy Sleeveless Smocked Tie-Dye Midi Swing Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Vintage Sleeveless Rib-Knit T-Shirt Midi Shift Dress

This grey Old Navy Vintage Sleeveless Rib-Knit T-Shirt Midi Shift Dress ($33, originally $35) is a good basic to own to wear in warmer weather out or just around the house (and if you're lucky you can also nab a peach or caramel one on sale, too).

Image Source: oldnavy.gap.com
Old Navy Vintage Sleeveless Rib-Knit T-Shirt Midi Shift Dress
$33
from oldnavy.gap.com
Buy Now

Want More?

POPSUGAR Would Like To Send You Push Notifications.