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Plus size Dresses Date Night

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  • Plus Size Flutter Sleeve Faux Leather DressFlutter Sleeve Faux Leather Dress

    Flutter Sleeve Faux Leather Dress - Egret

    $39.99
    $69.50
    $39.99
      23
    • Egret
      • 113
    • Black
      • 173
    • Tan
  • New
    Flounced Floral Sheath DressFlounced Floral Sheath Dress

    Flounced Floral Sheath Dress - Multi

    $39.99
    $69.50
    $39.99
      63
    • Multi
  • New
    Plisse Printed Maxi DressPlisse Printed Maxi Dress

    Plisse Printed Maxi Dress - Foxglove

    $39.99
    $69.50
    $39.99
      13
    • Foxglove
  • New
    Studded Maxi ShirtdressStudded Maxi Shirtdress

    Studded Maxi Shirtdress - Black

    $39.99
    $74.50
    $39.99
    Online Exclusive
      13
    • Black
      • 93
    • Pink Yarrow
  • New
    Plus Size Suede Dress Sheath Dress Plus Size Shift DressBell Sleeved Faux Suede Dress

    Bell Sleeved Faux Suede Dress - Foxglove

    $39.99
    $74.50
    $39.99
      13
    • Foxglove
      • 93
    • Camel Taupe
  • Plus Size Lace Up Sharkbite Sweater DressLace Up Sharkbite Sweater Dress

    Lace Up Sharkbite Sweater Dress - Heather Grey

    $39.99
    $69.50
    $39.99
    Online Exclusive
      13
    • Heather Grey
  • New
    Plus Size A Line Dress Plus Size Fit Flare Knit Semi Formal DressSplit Sleeved Scroll Print Dress

    Split Sleeved Scroll Print Dress - Foxglove

    $39.99
    $69.50
    $39.99
      13
    • Foxglove
  • New
    Plus Size Denim Maxi Sexy Evening Cowl Neck Jean Dress Cowl Neck Denim Maxi Dress

    Cowl Neck Denim Maxi Dress - Dk Rinse

    $39.99
    $69.50
    $39.99
    Online Exclusive
      33
    • Dk Rinse
  • New
    Floral Faux Wrap Maxi DressFloral Faux Wrap Maxi Dress

    Available in Lengths

    Floral Faux Wrap Maxi Dress - Black Combo

    $39.99
    $69.50
    $39.99
    Online Exclusive
      33
    • Black Combo
  • New
    Plus Size Sweater Dress Plus Size Ribbed Maxi Dress Matching SetFrayed Maxi Sweater Dress

    Matching Set

    Frayed Maxi Sweater Dress - Koi

    $39.99
    $59.50
    $39.99
    Online Exclusive
      13
    • Koi
      • 63
    • Lush Meadow
  • New
    Printed Paneled A Line DressPrinted Paneled A Line Dress

    Printed Paneled A Line Dress - Black Combo

    $39.99
    $69.50
    $39.99
      13
    • Black Combo
  • New
    Faux Leather Paneled A Line DressFaux Leather Paneled A Line Dress

    Faux Leather Paneled A Line Dress - Black

    $39.99
    $74.50
    $39.99
    Online Exclusive
      33
    • Black
  • New
    Two Tone A Line Maxi DressTwo Tone A Line Maxi Dress

    Available in Lengths

    Two Tone A Line Maxi Dress - Black White

    $39.99
    $74.50
    $39.99
    Online Exclusive
      13
    • Black White
  • New
    Plus Size Sweater Bolero Plus Size Shrug Plus Size Matching SetFrayed Knitted Bolero

    Matching Set

    Frayed Knitted Bolero - Koi

    $39.99
    $54.50
    $39.99
    Online Exclusive
      13
    • Koi
      • 63
    • Lush Meadow
  • New
    Plus Size A Line Dress Diamond Fit Flare Knit Semi Formal DressDiamond Print A Line Dress

    Diamond Print A Line Dress - Black Combo

    $39.99
    $64.50
    $39.99
      33
    • Black Combo
  • New
    Plus Size link print wrap dress black maxi wrap dress knit dressChain Link Print Faux Wrap Dress

    Available in Lengths

    Chain Link Print Faux Wrap Dress - Black Combo

    $39.99
    $69.50
    $39.99
      23
    • Black Combo
  • Plus Size Two Tone Tie Neck DressTwo Tone Tie Neck Dress

    Two Tone Tie Neck Dress - Black

    $39.99
    $64.50
    $39.99
    Online Exclusive
      13
    • Black
  • New
    Chambray Bubble DressChambray Bubble Dress

    Chambray Bubble Dress - Denim Blue

    Chambray takes on a playful shape in this bubble dress styled with a V-neck and a shirred waistband for definition. Elasticized sleeve cuffs and a gathered hem create that signature bubble effect, balancing structure with soft volume.
    $39.99
    $69.50
    $39.99
      13
    • Denim Blue
  • New
    Ruffled Denim Mini ShirtdressRuffled Denim Mini Shirtdress

    Ruffled Denim Mini Shirtdress - Dk Wash

    Flirty meets functional in this denim mini shirtdress, styled with flap chest pockets, side slit pockets, and ruffled elasticized cuffs for a playful finish. The elasticized waist with sash ties defines your curves while the zip-front closure keeps it sleek and effortless.
    $39.99
    $69.50
    $39.99
    Online Exclusive
      13
    • Dk Wash
  • New
    Faux Leather Joggers JumpsuitFaux Leather Joggers Jumpsuit

    Faux Leather Joggers Jumpsuit - Olive Night

    $39.99
    $79.50
    $39.99
      13
    • Olive Night
      • 73
    • Foxglove
  • New
    Cutout Watercolor Print Maxi DressCutout Watercolor Print Maxi Dress

    Cutout Watercolor Print Maxi Dress - Multi

    $39.99
    $69.50
    $39.99
      13
    • Multi
  • New
    Plisse Satin Balloon Pant JumpsuitPlisse Satin Balloon Pant Jumpsuit

    Plisse Satin Balloon Pant Jumpsuit - Caramel Cafe

    Plissé satin brings rich texture to this balloon pant jumpsuit designed with a clean V-neck and a softly sculpted shape. The result is an elegant, relaxed look that feels elevated and unmistakably luxe.
    $39.99
    $74.50
    $39.99
    Online Exclusive
      13
    • Caramel Cafe
      • 63
    • EDEN
  • Plus Size A Line Suede Dress Camel Fit Flare DressFaux Suede A Line Shirtdress

    Faux Suede A Line Shirtdress - Tan

    $39.99
    $74.50
    $39.99
    Online Exclusive
      13 163
    • EDEN
  • New
    Tie Neck Watercolor Maxi DressTie Neck Watercolor Maxi Dress

    Tie Neck Watercolor Maxi Dress - Multi

    $39.99
    $69.50
    $39.99
    Online Exclusive
      13
    • Multi
  • New
    Bandana Print ShirtdressBandana Print Shirtdress

    Bandana Print Shirtdress - POWDER BLUE

    This bandana print shirtdress hugs close with a fitted feel as the button-tab sleeves keep the look sharp and styled.
    $39.99
    $64.50
    $39.99
      13
    • POWDER BLUE
  • New
    Front Split Maxi DressFront Split Maxi Dress

    Front Split Maxi Dress - Black White

    $39.99
    $64.50
    $39.99
    Online Exclusive
      13
    • Black White
      • 173
    • Orange.com
  • New
    Textured Denim Sheath DressTextured Denim Sheath Dress

    Textured Denim Sheath Dress - Dk Rinse

    $39.99
    $69.50
    $39.99
      23
    • Dk Rinse
  • New
    Swirl Print Cowl Neck Maxi DressSwirl Print Cowl Neck Maxi Dress

    Available in Lengths

    Swirl Print Cowl Neck Maxi Dress - Multi

    This stretch-knit maxi dress combines a swirl print with a softly draped cowl neck. Fluid fabric and a relaxed fit create a look that’s visually dynamic.
    $39.99
    $69.50
    $39.99
    Online Exclusive
      13
    • Multi
  • Plus Size Perforate Effect Faux Leather DressPerforate Effect Faux Leather Dress

    Perforate Effect Faux Leather Dress - Black

    $39.99
    $89.50
    $39.99
      63
    • Black

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.