Dress for Comfort AND Fashion with These 7 Styles

These seven outfits look polished, pretty and put together. As for how they feel? Just like your favorite pajamas.

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Mixed Prints

mixed print dress eva mendes collection 2019

Patterns and animal prints are everywhere this season—and mixing them is the AP exam of fall fashion. A fail-proof approach is sticking to one color palette or rocking this plaid-and-snakeskin dress that takes away all the guesswork. Its pleated skirt and wrap-style adjustable closure make it a good fit for a range of body types.

Own it: Dress, Eva Mendes Collection at New York & Company, nyandcompany.com, $90. Earrings, $58, bracelets, $78 each, and ring, $70, shopsoko.com.

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Skirt on the Run

Sanctuary skirt on the run 2019

It only sounds too good to be true: a pencil silhouette with ample give in the waist and hips that actually allows you to take normal, human, non-penguin strides. And a sweater with elegant loose-fit sleeves is forgiving to the upper-arm area. Also helpful when you really need to hustle to catch your bus: The pull-on block-heel booties and a totally profesh tote that turns into a backpack in a pinch (or sprint).

Own it: Skirt, sanctuaryclothing.com, $79. (Available in inclusive sizing 1x–3x.) 25% off with code FAMILY25 through October 31. Sweater, whitehouseblackmarket.com, $99. Boots, bornshoes.com, $140. 15% off (sitewide!) with code FCFALL19. Bag, fossil.com, $218.

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Look of Leather

7 for all mankind camisole 2019

This is your go-to black leggings, tank and huge hoodie (swiped from your son’s dresser) but after your fashion fairy godmother stepped in. You’ll look perfectly presentable in a beyond-soft cami, a cozy oversized cardigan (just long enough to cover your butt, not that you need to!) and faux leather leggings with (thank you, style gods) shapewear technology to minimize your waistline. The shoes are pretty magical too: You can fine-tune and customize your order to accommodate a wide foot or even a bunion. 

Own it: Camisole, 7forallmankind.com, $125. Sweater, Vintage America, belk.com, $129. Leggings, spanx.com, $98–$102. Flats, margauxny.com, $145.

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Running Start

525 America joggers 2019

Yes, they’re the joggers you love and live in, but the Glen plaid pattern makes these pants safe for Monday–Friday, especially when paired with (are you sensing a trend?) leopard-print mules and a soft bateau-neck sweater.

Own it: Joggers, 525america.com, $118. 20% off (sitewide!) with code Family20. Sweater, eileenfisher.com, $398. Mules, ninewest.com, $99. Earrings, kendrascott.com, $78. 

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Down for Anything

Garnet hill puffer jacket 2019

Puffers are so warm, but they have a way of making you feel as big and unwieldy as the Stay Puft Marshmallow Man. But not with this style—which packs all the coziness into a sleek silhouette that feels more like you’re wearing a blazer. Toss it on over a metallic-accent houndstooth knit skirt with an elastic waistband and indestructible pleats. (Seriously, even your lovable-slob daughter could wear it without damaging it!)

Own it: Jacket, garnethill.com, $199. Skirt, 525america.com, $118. 20% off (sitewide!) with code Family20. Shoes, drschollsshoes.com, $70. Earrings, $139, and ring, $131, the9thmuse.com. 

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Jump for Joy

French Connection jump suit 2019

Jumpsuits are onesies for grown-ups, and this version is soft and flowy and moves with you. For an extra-comfy accessory, skip the chunky necklace and go for a statement scarf.

Own it: Jumpsuit, usa.frenchconnection.com, $188. Scarf, echodesign.com, $39. Sneakers, golausa.com, $95. Bracelet, jewelrybybloom.com, $130. 25% off with code FamilyCircle25. Bag, angelaroi.com, $240. Earrings, shopsoko.com, $64. 

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Preppy and Stretchy

cabionline blazer 2019

Finally, we’ve moved past that moment of snug, fitted, Bobby-Brady-put-his-suit-through-the-laundry blazers—and we’re on to jackets like this roomy double-breasted style that actually has panels of stretch fabric on the sleeves. Pair it with high-waisted cropped trouser jeans and tasseled flats for a modern-preppy vibe.

Own it: Blazer, cabionline.com, $189. Shirt, cosstores.com, $99. Jeans, talbots.com, $95. Flats, hushpuppies.com, $90. Ring, ready-made.co, $32. 10% off (sitewide!) with code FAMILY10. For 20% off an Etienne Aigner crossbody bag, turn to page 4.