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Plus size Dresses Date Night

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  • New
    Plus Size Layered Two Tone JumpsuitLayered Two Tone Jumpsuit

    Available in Lengths

    Layered Two Tone Jumpsuit - Black White

    Twice the tone, double the drama. This textured jumpsuit is all about easy chic, featuring a wide-leg silhouette and skirt overlay that flutters with each step.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Black White
  • New
    Strapless Denim Bodycon DressStrapless Denim Bodycon Dress

    Strapless Denim Bodycon Dress - Medium Blue

    This strapless stretch-denim maxi dress is made to turn heads with a curve-hugging fit, frayed trims & a thigh-high front split that does all the flirting for you. Just add heels and a little attitude.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Medium Blue
      • 93
    • Black
  • New
    Plus Size Layered Chambray Babydoll DressLayered Chambray Babydoll Dress

    Layered Chambray Babydoll Dress - Dk Rinse

    This chambray babydoll dress is your new must-have fun, flirty look! With a sassy V-neck, billowy bell sleeves, and sweet ruffled trims, it's as playful as it is stylish. The skirt overlay adds a little extra twirl to your step, making this dress the...
    $69.50
    $0.00
    $69.50
    Online Exclusive
      33
    • Dk Rinse
  • New
    Drama Sleeved Floral DressDrama Sleeved Floral Dress

    Drama Sleeved Floral Dress - Cyber Yellow

    This dress is a walking masterpiece. The floral print is serving, the V-neckline is tempting, and that front knot? Snatched to perfection. Drama sleeves with a cutout and a front split? Just the right amount of tease.
    $69.50
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      53
    • Cyber Yellow
  • Plus Size Knit Dress Plus Size Shirtdress Plus Size Midaxi DressTextured Knit Midaxi Shirtdress

    Textured Knit Midaxi Shirtdress - BlueBird

    Sun-kissed days call for this textured-knit midaxi shirtdress. Lightweight and effortlessly stylish, it features a classic button-down front and sash ties at the waist for a flattering fit.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • BlueBird
      • 93
    • Fandango Pink
  • Plus Size Knit Dress Plus Size Maxi Dress Plus Size Casual DressesRuched Knit Maxi Dress

    Ruched Knit Maxi Dress - Black

    This maxi bodycon dress was made to flatter, hug & turn up the heat up a notch. With sultry ruching at the shoulders and sides, it contours in all the right places, while the back split adds just the right amount of drama. Soft,...
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Black
      • 93
    • Frozen Fjord
  • Plus Size floral print shirt dress plus size summer dressesRuched Floral Print Shirtdress

    Ruched Floral Print Shirtdress - Denim Blue

    A little structure, a little stretch, and a whole lot of style. This floral print stretch-knit shirtdress brings a fresh take on a classic, with ruched detailing that flatters every curve. Soft, comfy, and ready for anything—button it up for a polished vibe or...
    $69.50
    $0.00
    $69.50
      13
    • Denim Blue
  • New
    Metallic Print DressMetallic Print Dress

    Metallic Print Dress - Black

    Shimmer meets everyday comfort in this metallic print woven dress. The linen-like fabric keeps things light, while side slit pockets add a laid-back feel. Just slip it on and shine your way through the day.
    $74.50
    $0.00
    $74.50
      13
    • Black
      • 93
    • White
  • Plus Size Dress Plus Size Spring Dresses Plus Size Fit Flare DressWindowpane Sleeved A Line Dress

    Windowpane Sleeved A Line Dress - Black

    Freshen up your spring wardrobe with this stretch-crepe dress, designed with airy windowpane mesh sleeve panels for a light, breezy feel. The A-line skirt adds soft movement, making it perfect for everything from daytime outings to evening plans. Just add your favorite heels or...
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Black
  • New
    Pleated Floral Maxi DressPleated Floral Maxi Dress

    Pleated Floral Maxi Dress - Purple Magic

    Pleats & petals are a lovely combination on our maxi dress blooming with flowers along the soft satin.
    $74.50
    $0.00
    $74.50
      23
    • Purple Magic
  • New
    Plus Size Paisley Faux Wrap Maxi DressPaisley Faux Wrap Maxi Dress

    Paisley Faux Wrap Maxi Dress - Fandango Pink

    Swirls on swirls! This paisley print maxi dress is all about looking good and feeling even better. The stretchy knit fabric moves with you, while the faux wrap neckline is a flirty stylish add.
    $69.50
    $0.00
    $69.50
      13
    • Fandango Pink
  • New
    Asymmetric Sequined Blazer DressAsymmetric Sequined Blazer Dress

    Asymmetric Sequined Blazer Dress - White

    Be the sequined star whether this look as a wedding guest, a birthday dress or upscale soiree. You don't just stop the show in this one-shoulder blazer dress...you steal it.
    $84.50
    $0.00
    $84.50
    Online Exclusive
      13
    • White
      • 93
    • Black
  • New
    Plus Size Paneled Polka Dot JumpsuitPaneled Polka Dot Jumpsuit

    Available in Lengths

    Paneled Polka Dot Jumpsuit - Black White

    Polka dots, power moves, and a whole lot of attitude, this wide-leg jumpsuit is serving everything. The stretch-knit fit hugs in all the right places, while the sash-ties let you cinch it just how you like. 
    $69.50
    $0.00
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    Online Exclusive
      13
    • Black White
  • Plus Size Organza Paneled A Line DressOrganza Paneled A Line Dress

    Organza Paneled A Line Dress - Black

    Graceful & refined, this stretch-knit dress is adorned with delicate organza neckties and sheer sleeve panels for a touch of ethereal charm. The flowing A-line skirt completes the look with timeless elegance.
    $69.50
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    Online Exclusive
      13
    • Black
  • Plus Size denim dress two tone colorblock chambray dress midaxi dressTwo Tone Chambray Midaxi Dress

    Two Tone Chambray Midaxi Dress - Denim

    Easygoing style meets standout design in this two-tone chambray midaxi dress. The ruched front detail creates a flattering fit, while sash ties at the waist let you customize your shape. Finished with a dipped back hemline for a flowy touch, it’s the perfect mix...
    $69.50
    $0.00
    $69.50
      13
    • Denim
  • New
    Plus Size Midi Dress Plus Size Semi Formal Dress Tieneck DressTie Neck Flounced Midi Dress

    Tie Neck Flounced Midi Dress - Jade Lime

    With dainty neckties & a flounced hem that sways just so, this midi dress brings a soft, romantic feel to every step. Whether you're wandering through a garden or sipping something sweet at a picnic, it’s made for moments that linger.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Jade Lime
      • 93
    • LILAC
  • New
    Plus Size Belted Denim Wide Leg JumpsuitBelted Denim Wide Leg Jumpsuit

    Belted Denim Wide Leg Jumpsuit - Black White

    This stretch-denim jumpsuit does all the talking with a tailored vest-style bodice that means business & wide legs that know how to walk into a room. The sash-tie waist lets you cinch it how you want, when you want.
    $79.50
    $0.00
    $79.50
    Online Exclusive
      13
    • Black White
  • New
    Watercolor Print Halter DressPlus Size Watercolor Print Halter Dress

    Watercolor Print Halter Dress - Navy Peony

    This dress is pure poetry in motion. The dreamy watercolor floral print, the flirty swing silhouette, the ruffled halterneck trims—every detail is serving soft and playful.
    $69.50
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    $69.50
      13
    • Navy Peony
  • Plus Size Leopard Shirtdress Plus Size Twill Dress Denim DressLeopard Cotton Twill Shirtdress

    Leopard Cotton Twill Shirtdress - Black Animal

    This leopard print cotton-twill styles mixes the classis look of a shirtdress with untamed attitude!!! the design features elasticized sleeve cuffs & a cinched waistband for the perfect fit. Side slit pockets keep it cool and casual, while the A-line hemline brings a touch...
    $69.50
    $0.00
    $69.50
      23
    • Black Animal
  • Plus Size Bodycon Dress Plus Size Knit DressAbstract Print Midi Bodycon Dress

    Abstract Print Midi Bodycon Dress - Multi

    Bring the attitude in this abstract print stretch-knit midi dress. With a curve-hugging bodycon fit, a sultry V-neckline, figure-flattering ruching & a flirty front split, it’s serving drama in all the right places. Just add your favorite heels and get ready to steal the...
    $64.50
    $0.00
    $64.50
      33
    • Multi
  • New
    Plus Size Denim Print Wide Leg JumpsuitDenim Print Wide Leg Jumpsuit

    Available in Lengths

    Denim Print Wide Leg Jumpsuit - Blue

    Bet on denim (or at least the look of denim!) in our wide-leg jumpsuit made with a patchwork denim print.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Blue
  • Plus Size retro square print dress mesh dress plus size sheath dressSquare Print Mesh Sheath Dress

    Square Print Mesh Sheath Dress - Multi

    Geometric glam with a sleek edge. This stretch-mesh midaxi sheath dress hugs in all the right places, featuring a bold square print that channels retro energy. Lightweight and breathable with just the right amount of stretch, it moves with you from day to night.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • New
    Plus Size Off The Shoulder Printed Mesh DressOff The Shoulder Printed Mesh Dress

    Off The Shoulder Printed Mesh Dress - BlueBird

    Fit for a fashionista who is ready to take the night, the wavy pattern of this print is a genius complement to the mesh fabric of our midaxi dress. We serve a little shoulder action for a coquette-inspired moment.
    $69.50
    $0.00
    $69.50
      13
    • BlueBird
  • New
    Plus Size Floral Pleated Maxi DressFloral Pleated Maxi Dress

    Floral Pleated Maxi Dress - Cyber Yellow

    Pleats & petals are a lovely combination on our maxi dress blooming with flowers along the soft satin.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • Cyber Yellow
  • New
    Plus Size Midi Dress Plus Size Semi Formal Dress Little White DressFlounced Tie Neck Midi Dress

    Flounced Tie Neck Midi Dress - White

    With dainty neckties & a flounced hem that sways just so, this midi dress brings a soft, romantic feel to every step. Whether you're wandering through a garden or sipping something sweet at a picnic, it’s made for moments that linger.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • White
  • New
    Plus Size Off The Shoulder Orchid Print DressOff The Shoulder Orchid Print Dress

    Off The Shoulder Orchid Print Dress - Black Combo

    Get ready to stop traffic in this off-the-shoulder orchid print maxi dress! With ruched detailing that hugs your curves and a daring side split, this bodycon beauty serves!!!
    $69.50
    $0.00
    $69.50
      13
    • Black Combo
  • New
    Plus Size Polka Dot Shirt Dress Plus Size Spring Dress Organza DressPolka Dot Organza Shirtdress

    Polka Dot Organza Shirtdress - White Black

    Lighten up your look with this airy polka dot organza shirtdress. Sheer, floaty & perfect for Summer, the elasticized sleeve cuffs bring a soft blouson shape, while sash-ties cinch the waist just how you like. Comes with a detachable stretch-knit slip for just the...
    $79.50
    $0.00
    $79.50
    Online Exclusive
      13
    • White Black
  • New
    Plus Size chambray jumpsuit plus size denim jumpsuit plus size overallsBelted Chambray Jumpsuit

    Belted Chambray Jumpsuit - Denim Blue

    Light wash chambray sets the stage for utility chic on our straight-leg jumpsuit. Snatch the waist with the detachable sash ties or keep it chill without, it's your world & your rules!!!
    $69.50
    $0.00
    $69.50
      23
    • Denim Blue
  • New
    Plus Size Brushstroke Print Dress Plus Size Hi Low Dress Cotton DressesBrushstroke Print Hi Low Dress

    Brushstroke Print Hi Low Dress - Purple Magic

    Splashed in a painterly brushstroke print and cut from a breathable cotton-linen blend, it’s made for sun-drenched days and spontaneous plans. Braided trims trace the silhouette with just enough detail, while a cotton panel adds structure where it counts. The hi-low hemline? Let’s just...
    $64.50
    $0.00
    $64.50
      13
    • Purple Magic
  • Plus Size Spring Dress Plus Size Paisley Print Summer Dress Paisley Print Swing Dress

    Paisley Print Swing Dress - Black White

    Flowy, fun, and full of charm—this paisley print crepe swing dress is made to move with you. The easy silhouette keeps things light, while a pleated collar add a touch of texture and dimension.
    $69.50
    $0.00
    $69.50
      13
    • Black White

Recently Viewed Products

Make a Lasting Impression With The Perfect Date Night Dress

Date night calls for a stand-out look, and Ashley Stewart carries plus-size dresses in a variety of styles to help make your next date night one to remember. Whether it’s a planned date or a surprise, it’s always helpful to have a great date night dress at the ready. For formal occasions, maxi dresses offer a long and elegant look and can be accessorized for any event. If you’re thinking a date on the move is the go-to, midi dresses offer both the flexibility to be casual, but they are also perfect year-round. Get the date night dress that suits you with long sleeve, short sleeve, and sleeveless dress styles. Dance the night away in eye-catching designs with embellishments, ruffles, lace or cutouts. There’s a pretty, flattering dress waiting for you to add to your date night outfits. Shop our trending plus size party dresses in comfortable, bold, stylish plus size dress styles.

Shop Plus Size Clothing Online or In-Store

Find the perfect dress for your next date night online, or find an Ashley Stewart location near you.