Popsugar Fashion Fashion Shopping Most Comfortable Midi Dresses From Old Navy 20 Comfy Old Navy Midi Dresses That'll Make You Forget Any Other Outfit Option 17 August 2021 by Morgan Ashley Parker Image Source: Old Navy 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. Related: My New Favourite Thing Is This $33 Old Navy Linen Dress — I Wore for 14 Hours Straight Old Navy Sleeveless Waist-Defined Slub-Knit Midi Dress Image Source: oldnavy.gap.com 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. Old Navy Sleeveless Waist-Defined Slub-Knit Midi Dress $30 from oldnavy.gap.com Buy Now Old Navy French-Terry Sweatshirt Midi Shift Dress Image Source: oldnavy.gap.com It truly doesn't get much more comfortable than this Old Navy French-Terry Sweatshirt Midi Shift Dress ($45) when lounging at home. 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. Old Navy Sleeveless Cross-Back Rib-Knit Midi Shift Dress $37 from oldnavy.gap.com Buy Now Old Navy Smocked Off-the-Shoulder Chambray Fit and Flare Midi Dress Image Source: oldnavy.gap.com 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). 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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). 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 Image Source: oldnavy.gap.com 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). 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com Swing into a new season with this Old Navy Dobby Bell-Sleeve Midi Swing Dress ($45) and sandals, slides, or sneakers. Old Navy Dobby Bell-Sleeve Midi Swing Dress $45 from oldnavy.gap.com Buy Now Old Navy Long-Sleeve Midi Sweatshirt Shift Dress Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. Old Navy UltraLite Performance Racer-Back Ribbed Midi Dress $30 from oldnavy.gap.com Buy Now Old Navy Vintage Sleeveless Striped Midi Shift Dress Image Source: oldnavy.gap.com 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. Old Navy Vintage Sleeveless Striped Midi Shift Dresses $35 from oldnavy.gap.com Buy Now Old Navy Puff-Sleeve Tiered Striped Midi Swing Dress Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com Why not grab a charcoal Old Navy Fit and Flare Short-Sleeve Tiered Midi Dress ($40) for your go-to casual fall dress? 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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). Old Navy Vintage Sleeveless Rib-Knit T-Shirt Midi Shift Dress $33 from oldnavy.gap.com Buy Now ShoppingFashion ShoppingOld NavyDresses