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Plus size Dresses Date Night

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  • Plus Size scarf print maxi dress plus size wrap dress plus size sundressScarf Print Maxi Dress

    Scarf Print Maxi Dress - Surf The Web

    Make a statement in this blue and white scarf print crepe maxi dress. The faux wrap neckline and bell sleeves add flowy elegance, while the elasticized waistband creates a flattering, comfortable fit. With a slip-on style that’s both easy and stylish, this dress is...
    $74.50
    $0.00
    $74.50
      33
    • Surf The Web
  • Plus Size knit dress plus size sheath dress plus size shift spring dressPrinted Textured Knit Sheath Dress

    Printed Textured Knit Sheath Dress - Fandango Pink

    Soft hues and fresh vibes make this pink and white printed textured-knit sheath dress a perfect pick for spring. The flattering V-neckline adds a touch of sophistication, while the bell sleeves bring a playful, feminine flair.
    $69.50
    $0.00
    $69.50
      63
    • Fandango Pink

  • DENIM/099-SKTEST05212507 - Poplin Beige

    DENIM/099-SKTEST05212507
    $39.99
    $39.99
      13
    • Poplin Beige
  • Plus Size Cutout Brushstroke A Line DressCutout Brushstroke A Line Dress

    Cutout Brushstroke A Line Dress - Dark Citron

    This brushstroke print dress is here to shake things up. The textured knit keeps it fresh, the mock neck and cutout serve just enough tease and the A-line skirt is ready for whatever the day throws your way.
    $69.50
    $0.00
    $69.50
      13
    • Dark Citron
  • Plus Size Printed Midaxi Bodycon DressPrinted Midaxi Bodycon Dress

    Printed Midaxi Bodycon Dress - Multi

    Printed to pop and cut to cling, this midaxi bodycon doesn’t hold back. The flounced hem brings the sass with every step and the tie-back keyhole seals the deal from behind.
    $69.50
    $0.00
    $69.50
      53
    • Multi
  • Plus Size Yellow Denim Dress Plus Size Jean Dress Cotton DressCuffed Denim Dress

    Cuffed Denim Dress - Nugget Gold

    This midi denim dress features a shirred waistband that shapes without fuss. Side slit pockets hold your must-haves or whatever else you stash. Button tabs on the cuffed sleeves let you adjust the style on the fly.
    $69.50
    $0.00
    $69.50
      13
    • Nugget Gold
  • Plus Size Red Denim Dress Plus Size Jean Dress Plus Size Cotton DressCuffed Sleeve Denim Dress

    Cuffed Sleeve Denim Dress - BIKING RED

    This midi denim dress features a shirred waistband that shapes without fuss. Side slit pockets hold your must-haves or whatever else you stash. Button tabs on the cuffed sleeves let you adjust the style on the fly.
    $69.50
    $0.00
    $69.50
      13
    • BIKING RED
  • Plus Size Leopard Print Bodycon DressLeopard Print Bodycon Dress

    Leopard Print Bodycon Dress - Black Animal

    This leopard print bodycon dress isn’t here to play nice. Made from curve-hugging stretch scuba with short sleeves and a slip-on fit, it’s fierce, fun, and ready to pounce. Wear it loud and own every second.
    $59.50
    $0.00
    $59.50
      13
    • Black Animal
  • Plus Size Belted Faux Wrap DressBlack Wrap Dress with Ruffle Hem

    Black Wrap Dress with Ruffle Hem - Black

    Make a bold statement in this timeless black wrap dress designed with a deep V-neckline, long sleeves, and a midi silhouette that moves with you. The self-tie waist lets you customize your fit, while the ruffle hem adds playful texture and dimension. Perfect for...
    $64.50
    $0.00
    $64.50
      13
    • Black
      • 73
    • Dusk Blue
      • 123
    • BIKING RED
  • Plus Size Textured Geo Print A Line DressTextured Geo Print A Line Dress

    Textured Geo Print A Line Dress - Multi

    This geo print dress is serving retro realness with a modern kick. The textured knit keeps it fun, the cutout brings the tease and the A-line skirt is made to move. Toss in side pockets and you’ve got a throwback look that's ready to...
    $69.50
    $0.00
    $69.50
      23
    • Multi
  • Plus Size Ruched Printed Mesh DressRuched Printed Mesh Dress

    Ruched Printed Mesh Dress - Green

    Serving body with a side of wave. This printed mesh midi clings just right with a mock neck and subtle ruching.
    $69.50
    $0.00
    $69.50
      13
    • Green
  • Plus Size Leather Sheath Dress Plus Size Camel Leather Midi DressPoplin Paneled Faux Leather Dress

    Poplin Paneled Faux Leather Dress - Cognac

    Layer game strong. This faux leather midi dress fakes the fuss with built-in stretch-poplin panels and a belted waist. Buttoned cuffs seal the deal for a one-and-done look that serves all the layers without the work.
    $79.50
    $0.00
    $79.50
      13
    • Cognac
  • Plus Size Bow Intarsia SweaterBow Intarsia Sweater

    Bow Intarsia Sweater - EQUESTRIAN RED

    Bows gone baddie in this flirty intarsia-knit sweater with black bow motifs and turns up the charm even more when paired with the matching skirt.
    $44.50
    $0.00
    $44.50
      13
    • EQUESTRIAN RED
  • Plus Size Swirl Maxi BodyconSwirl Maxi Bodycon

    Swirl Maxi Bodycon - Multi

    Shades of black swirl with aubergine and caramel in this maxi bodycon. Mock neck is chic & the side slit turns up the temp.
    $64.50
    $0.00
    $64.50
      13
    • Multi
  • Plus Size Fringed Faux Wrap DressFringed Faux Wrap Dress

    Fringed Faux Wrap Dress - Black

    Fringe in motion makes this crepe dress a standout. The faux wrap neckline keeps it sleek, button cuffs add polish and the cinched waist shapes it all into a look that owns the room.
    $79.50
    $0.00
    $79.50
      13
    • Black
      • 93
    • Potting Soil
  • Pleated Bow Mini SkirtPlus Size Pleated Bow Mini Skirt

    Pleated Bow Mini Skirt - EQUESTRIAN RED

    Swing into sweet mischief with this pleated mini skirt. Black bows pop against red as the elasticized waistband keeps it teasingly snug made even more irresistible with the matching sweater.
    $44.50
    $0.00
    $44.50
      13
    • EQUESTRIAN RED
  • Plus Size Mesh Paneled Floral Midaxi DressMesh Paneled Floral Midaxi Dress

    Mesh Paneled Floral Midaxi Dress - Multi

    You're a floral fantasy in our printed midaxi dress. Mesh sleeves and neck panels sneak a peek of skin as the bodycon fit fashionably flexes your curves.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • Plus Size Greek Key A Line DressGreek Key A Line Dress

    Greek Key A Line Dress - Black White

    Classic with a pinch of spice, this Greek key dress slips on easy with an A-line skirt that swings with style.
    $64.50
    $0.00
    $64.50
      13
    • Black White
  • Plus Size Plaid Shirtdress Plus Size Cotton High Low Fit Flare DressPlaid A Line Shirtdress

    Plaid A Line Shirtdress - Black Combo

    Plaid gets a pretty upgrade in this cotton-blend shirtdress. This style shows off with a V-neckline, buttoned cuffs and a sash-tied waist that flatters every time. The dipped back and A-line skirt adds a dramatic effect, just the kind that works for both desk...
    $59.50
    $0.00
    $59.50
      13
    • Black Combo
  • Plus Size Cold Shoulder Maxi DressCold Shoulder Maxi Dress

    Cold Shoulder Maxi Dress - Nugget Gold

    Shoulders out, confidence up. This stretch-knit maxi dress is *chef's kiss* with cold-shoulder cutouts, a sleek mock neckline, front splits and a bold belt detail that pulls it all together.
    $64.50
    $0.00
    $64.50
      13
    • Nugget Gold
      • 73
    • Rhododendron
  • Plus Size Off The Shoulder Denim DressOff The Shoulder Denim Dress

    Off The Shoulder Denim Dress - Pink

    Off-the-shoulder & out of this world, explore the range of fashion showcased in this denim maxi dress designed to mimic your favorite jeans with a sexy split framed in fray trims.
    $69.50
    $0.00
    $69.50
      53
    • Pink
  • Plus Size Status Print Wrap DressStatus Print Wrap Dress

    Status Print Wrap Dress - Black Combo

    Every boss baddie knows a wrap dress is a staple for maintaining a well-rounded closet. Add a punch of level to your classics in our style designed in a fabulous status print with traditional wrap ties.
    $69.50
    $0.00
    $69.50
      13
    • Black Combo

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.