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Plus size Dresses Date Night

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  • New
    Plus Size Maxi Dress Yellow Infinity Dress Multi Way DressMulti Way Convertible Dress

    Multi Way Convertible Dress - Light/Pastel Yellow

    One dress, infinite options. Try on our maxi dress— made from stretchy knit with neck ties that allow you to style this dress based on the mood & the vibes.
    $84.50
    $0.00
    $84.50
    Online Exclusive
      13
    • Light/Pastel Yellow
  • New
    Plus Size Maxi Dress Blue Infinity Dress Multi Way DressMulti Way Maxi Convertible Dress

    Multi Way Maxi Convertible Dress - Lt Sky Blue

    One dress, infinite options. Try on our maxi dress— made from stretchy knit with neck ties that allow you to style this dress based on the mood & the vibes.
    $84.50
    $0.00
    $84.50
    Online Exclusive
      13
    • Lt Sky Blue
  • New
    Plus Size Maxi Dress Orange Infinity Dress Multi Way DressMaxi Convertible Dress

    Maxi Convertible Dress - Orange

    One dress, infinite options. Try on our maxi dress— made from stretchy knit with neck ties that allow you to style this dress based on the mood & the vibes.
    $84.50
    $0.00
    $84.50
    Online Exclusive
      13
    • Orange
  • New
    Plus Size Wide Leg Jumpsuit Summer Sleeveless Woven JumpsuitWoven Wide Leg Jumpsuit

    Woven Wide Leg Jumpsuit - Caribbean Sea

    Low-key and warm-weather approved, this woven wide-leg jumpsuit keeps it simple with a clean V-neck and adjustable straps for a perfect fit.
    $49.50
    $0.00
    $49.50
      13
    • Caribbean Sea
      • 93
    • Olive Night
  • New
    Printed Faux Wrap Maxi DressPrinted Faux Wrap Maxi Dress

    Available in Lengths

    Printed Faux Wrap Maxi Dress - Multi

    Twirl in swirls of color as you sashay your way through the day in our printed maxi with a faux wrap bodice and a-line skirt.
    $69.50
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    $69.50
      23
    • Multi
  • New
    Dotted Two Tone Maxi DressDotted Two Tone Maxi Dress

    Dotted Two Tone Maxi Dress - Macaw Green

    Crepe shifts the mood causing instant smiles from the beauty of it all. Lurex™ dots glisten against the two-tone fabric with a side split for a dose of sexy.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • Macaw Green
      • 93
    • Calypso Coral
  • New
    Paneled Floral Satin DressPaneled Floral Satin Dress

    Paneled Floral Satin Dress - Calypso Coral

    Structured scuba contrasts with glossy floral satin in this paneled dress designed with mixed textures in mind. A dramatic sleeve on one side balances the sleeveless cut on the other with a belted waist to sharpen the shape of the silhouette.
    $74.50
    $0.00
    $74.50
      13
    • Calypso Coral
  • New
    Strapless Leaf Print JumpsuitStrapless Leaf Print Jumpsuit

    Available in Lengths

    Strapless Leaf Print Jumpsuit - Sodalite

    Our strapless leaf print jumpsuit is giving vacation without the itinerary. The shirred bodice keeps things in place without fuss with the ruffle edge that adds a little coquette energy to the mix. Wide legs lets you relax without looking undone.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      23
    • Sodalite
  • New
    Plus Size sheath dress plus size church dress plus midaxi knit dressColorblock Midaxi Sheath Dress

    Colorblock Midaxi Sheath Dress - Black Combo

    A minimalist take on the classically chic dress, we elevate the style with the midaxi length and panels of neutral colors.
    $49.50
    $0.00
    $49.50
      13
    • Black Combo
  • New
    Plus Size Maxi Dress Floral Print Dress Flowers Summer DressFloral Chain Trimmed Maxi Dress

    Floral Chain Trimmed Maxi Dress - Multi

    Blooming florals make this satin maxi feel made for long, warm days. Chain shoulder straps add a hint of shine with a silhouette that keeps things easy and fluid.
    $69.50
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    $69.50
      13
    • Multi
  • New
    Plus Size Wrap Wide Leg Printed Jersey Knit Sleeveless JumpsuitPlus Size Wrap Wide Leg Printed Jersey Knit Sleeveless Jumpsuit

    Printed Balloon Leg Jumpsuit - Multi

    Bold print, flowing lines and a faux wrap give this jumpsuit a cool, head-turning feel. The trendy balloon pants-style legs are cause for attention and presence whether it’s rooftop plans, vacation dinners or wherever the night lands.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Plus Size Printed Romper Vacation Ready Short JumpsuitTropical Print Romper

    Tropical Print Romper - Olive

    Vacation energy in one step. This tropical print romper keeps it easy with a soft stretch feel and sash ties at the waist for that just-right shape, ready for whatever the day turns into.
    $69.50
    $0.00
    $69.50
      13
    • Olive
  • Plus Size Pink Maxi Dress V Neck Aline Fit Flare Poplin DressTie Back A Line Maxi Dress

    Tie Back A Line Maxi Dress - Calypso Coral

    Crisp poplin gives this maxi dress a clean touch to the hand & a joy to behold with a V-neck and softly gathered waist. An A-line skirt adds gentle volume as tie fastenings at the back finish the look with a neat, adjustable touch.
    $69.50
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      23
    • Calypso Coral
      • 93
    • Canary Yellow
  • New
    Off The Shoulder Floral JumpsuitOff The Shoulder Floral Jumpsuit

    Off The Shoulder Floral Jumpsuit - Fandango Pink

    Off-the-shoulder & ready to cause a little trouble. Our jumpsuit awakens the good vibes with it's billowing cut and wide-leg silhouette. It slips on easy, feels good instantly and somehow makes even simple plans feel like an occasion.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      43
    • Fandango Pink
  • New
    Abstract Print Maxi DressAbstract Maxi Dress

    Available in Lengths

    Abstract Maxi Dress - Sodalite

    Our abstract print maxi dress skims the body with a side slit for ease and a subtle flash as you walk.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Sodalite
  • New
    Ruffled Watercolor DressRuffled Watercolor Dress

    Ruffled Watercolor Dress - Multi

    Soft watercolor print on shantung gives this dress an artful feel complete with ruffle trims and sash ties that define the waist. The flounced hem brings a light, swaying finish as you move.
    $69.50
    $0.00
    $69.50
      43
    • Multi
  • New
    Plus Size Printed Mesh Maxi Dress Sleeveless Tank Summer Slip DressPlus Size Printed Mesh Maxi Dress Sleeveless Tank Summer Slip Dress

    Printed Mesh Maxi Slip Dress - Multi

    Slip into something a big sexier (and comfortable) than your usual summer wares with our vacation-inspired printed slip dress. The maxi length allows you to be as demure as you'd please with the soft mesh moving you through your day looking as hot as...
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Multi
  • New
    Strapless Floral Maxi DressStrapless Floral Maxi Dress

    Strapless Floral Maxi Dress - White

    Sun-warmed skin, a slow sway and ripples of drama. This strapless floral bodycon stretches along your curves before giving way to a teasing, drawstring split framed in ruffles that you can play up or pull back.
    $49.50
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    $49.50
    Online Exclusive
      13
    • White
      • 43
    • Poinsettia
  • New
    Off The Shoulder Geo Maxi DressOff The Shoulder Geo Maxi Dress

    Available in Lengths

    Off The Shoulder Geo Maxi Dress - Multi

    Off the shoulder and fully in your element. This stretch-knit maxi brings the energy with an electric, multicolored geo print that isn't shy. The flounce shimmies while everything else follows your lead. It moves when you move, and yes, people will be obsessed.
    $69.50
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    $69.50
    Online Exclusive
      23
    • Multi
  • Plus Size pompom sun maxi dress plus size trendy summer dressPompom Maxi Dress

    Pompom Maxi Dress - Canary Yellow

    A light, textured weave gives this maxi a soft drape constructed with a V-neck and side slits. Pompom accents are whimsical and texturally pleasing keeping things feeling lively and unforced.
    $69.50
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    $69.50
      13
    • Canary Yellow
      • 93
    • White
  • Plus Size Dress A Line Little White Dress Fit Flare Dress Knit DressTextured A Line Dress

    Textured A Line Dress - White

    This textured-knit dress features a sexy cutout with a sleek bar embellishment plus side slit pockets for that effortless cool factor. Finished with an A-line skirt that moves with you, it’s the perfect mix of structure and style.
    $64.50
    $0.00
    $64.50
      13
    • White
  • New
    Sequined Denim ShirtdressSequined Denim Shirtdress

    Sequined Denim Shirtdress - White

    Clean girl? Close. This white denim shirtdress takes things further with iridescent sequins scattered all over for the kind of low-effort flex people stare at a little too long.
    $74.50
    $0.00
    $74.50
      13
    • White
  • New
    Strapless Drawstring Maxi DressStrapless Drawstring Maxi Dress

    Strapless Drawstring Maxi Dress - Lime Green

    There's nothing subtle about this strapless maxi bodycon dress cut close with an elasticized bustline and an adjustable drawstring split that lets you decide how much leg to show. The ruffled trims keep it from feeling too serious as the whole silhouette does exactly...
    $49.50
    $0.00
    $49.50
    Online Exclusive
      13
    • Lime Green
      • 43
    • White
  • New
    Plus Size Bandeau Jumpsuit Leaf Print Summer Strapless JumpsuitStrapless Leaf Print Jumpsuit

    Strapless Leaf Print Jumpsuit - Victoria Blue

    Strapless & covered in a bold leaf print, this woven wide-leg jumpsuit stands out with a wide-leg silhouette and a layered bust overlay for dimension.
    $59.50
    $0.00
    $59.50
      33
    • Victoria Blue
  • New
    Tile Print Satin Maxi DressTile Print Satin Maxi Dress

    Tile Print Satin Maxi Dress - Multi

    Looks like the kind of dress that accidentally gets all the compliments. This tile print satin maxi brings the shine with a faux wrap neckline and an easy flow that eats at dinner, drinks and every plan after.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Plus Size Maxi Dress Plus Size Floral Dress Flowers Summer DressChain Trimmed Floral Maxi Dress

    Chain Trimmed Floral Maxi Dress - Primrose Yellow

    Liquid satin & bold florals set the stage for this spring maxi dress. Chain shoulder straps adds shine and the perfect built-in jewels with a flounced hem that bounces when you step.
    $74.50
    $0.00
    $74.50
      43
    • Primrose Yellow
  • New
    Embroidered Off The Shoulder DressEmbroidered Off The Shoulder Dress

    Embroidered Off The Shoulder Dress - Orangeade

    Softly dramatic with a hint of shimmer. This off-the-shoulder dress features a ruffled elasticized neckline that frames the shoulders, metallic-thread embroidery that's reflective & brilliant and pleated sleeve details for extra texture.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • Orangeade
      • 93
    • Peacoat
  • New
    Off The Shoulder Maxi DressOff The Shoulder Maxi Dress

    Available in Lengths

    Off The Shoulder Maxi Dress - Bud Green

    The kind of dress that makes every sidewalk feel a little cinematic, our off-the-shoulder maxi keeps it sweet & simple with a floaty shape and flounced hem.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Bud Green
      • 103
    • Primrose Yellow
  • New
    Tie Front Floral Print DressTie Front Floral Print Dress

    Tie Front Floral Print Dress - Seafoam

    A ruched bodice pulls everything with a touch of intention for a soft, delicate feel. At the bust, a delicate keyhole with tie fastenings makes for intrigue as you dilly and dally through the summer.
    $49.50
    $0.00
    $49.50
    Online Exclusive
      13
    • Seafoam
      • 43
    • Sodalite
  • New
    Printed Smocked Maxi DressPrinted Smocked Maxi Dress

    Printed Smocked Maxi Dress - Multi

    Our printed cotton-blend maxi dress has a weightless feel and a fun summery pattern. The smocked bodice is textural appealing and flexible shape keeping it comfortable through the day.
    $69.50
    $0.00
    $69.50
      13
    • Multi

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.