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Plus size Dresses Date Night

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  • New
    Flutter Sleeve Faux Leather DressFlutter Sleeve Faux Leather Dress

    Flutter Sleeve Faux Leather Dress - Black

    Flutter sleeves flirt & balance out the sweet silhouette of our faux leather a-line dress.
    $69.50
    $0.00
    $69.50
      23
    • Black
      • 103
    • Egret
      • 173
    • Tan
  • Belted Cable Knit Sweater DressBelted Cable Knit Sweater Dress

    Belted Cable Knit Sweater Dress - Caramel Cafe

    Welcome #sweaterszn in style thanks to our cable knit sweater dress designed with a waist-cinching belt.
    $69.50
    $0.00
    $69.50
      43
    • Caramel Cafe
      • 123
    • Heather Grey
      • 193
    • EDEN
      • 253
    • MAUVE WINE
  • New
    Plus Size Hearts Sweater Dress Plus Size Valentines Day Midi SetHeart Fringed Midi Sweater Dress

    Matching Set

    Heart Fringed Midi Sweater Dress - Lychee

    Soft hearts meet soft texture in this sexy midi dress. The eyelash knit gives each heart a sweet, touchable feel while the carwash fringe sways with every step. Pair it with the matching bolero for a two-piece look that leans into romance in the...
    $64.50
    $0.00
    $64.50
      23
    • Lychee
  • New
    Plus Size Paneled Faux Leather A Line DressPaneled Faux Leather A Line Dress

    Paneled Faux Leather A Line Dress - Black

    This faux leather dress is an instant hit with ruched sleeves and playful textured-knit panels along the A-line skirt.
    $74.50
    $0.00
    $74.50
      43
    • Black
      • 93
    • Green
  • New
    Plus Size Hearts Cropped Sweater Plus Size Valentines Day Bolero SetHeart Knitted Bolero

    Matching Set

    Heart Knitted Bolero - Lychee

    All charm, all sweetness. This heart-kissed bolero is dreamy with its fluttery eyelash texture and open-front silhouette. Slip it over the matching dress for a two-piece moment that feels tender, feminine and designed for a little romance.
    $49.50
    $0.00
    $49.50
      23
    • Lychee
  • New
    Faux Leather Paneled A Line DressFaux Leather Paneled A Line Dress

    Faux Leather Paneled A Line Dress - Black

    This stretch-knit maxi sets a new mood with a faux leather a-line skirt that instantly changes the game. Soft up top, slick down below, it gives you that bold-meets-sleek contrast without saying a word.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      33
    • Black
  • New
    Studded Maxi ShirtdressStudded Maxi Shirtdress

    Studded Maxi Shirtdress - Black

    Softly woven and sprinkled with studs, this maxi shirtdress drapes with effortless charm. Buttoned through the front, it flows with a gentle grace that carries you from sunlit strolls to evening fun.
    $74.50
    $0.00
    $74.50
    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

    Soft faux suede meets sleek tailoring in this sheath dress. The V-neck and bell-sleeve cuffs add subtle drama making it a piece that moves from day to night without missing a beat.
    $74.50
    $0.00
    $74.50
      13
    • Foxglove
      • 93
    • Camel Taupe
  • New
    Plus Size Denim Maxi Sexy Evening Cowl Neck Jean Dress Cowl Neck Denim Maxi Dress

    Cowl Neck Denim Maxi Dress - Dk Rinse

    Denim is constructed into a sultry cowl neck for a look that feels confident and sexy. The textured finish adds depth to the long, clean line. Available in regular and tall lengths.
    $69.50
    $69.50
    Online Exclusive
      23
    • Dk Rinse
  • New
    Frayed Maxi Sweater DressFrayed Maxi Sweater Dress

    Matching Set

    Frayed Maxi Sweater Dress - Lush Meadow

    Wrap yourself in soft ribbed warmth with this maxi sweater dress. The V-neck, frayed trims, and side split incorporate personality & charm, making it easy to style with the matching bolero or worn alone for a pop of color against Winter blues.
    $59.50
    $0.00
    $59.50
    Online Exclusive
      13
    • Lush Meadow
      • 63
    • Koi
  • New
    Plus Size Perforate Effect Faux Leather DressPerforate Effect Faux Leather Dress

    Perforate Effect Faux Leather Dress - Black

    Make your presence known in our perforated faux leather dress. Whether you're attending a fashion event, a night out with friends or just want to express your individuality, this dress embodies the perfect blend of bold and feminine aesthetics. The flounced hem adds a...
    $89.50
    $0.00
    $89.50
      43
    • Black
  • New
    Plus Size Printed Faux Wrap Midi DressPrinted Faux Wrap Dress

    Printed Faux Wrap Dress - Multi

    Wrapped up in style, you're an amazing sight to see in this faux wrap dress that accentuates your decolletage balanced with waist tie.
    $69.50
    $0.00
    $69.50
      63
    • Multi
  • New
    Paneled Faux Leather A Line DressPaneled Faux Leather A Line Dress

    Paneled Faux Leather A Line Dress - Black

    Step into sweet style with our faux leather and stretch-knit dress, designed for the girly girl with a bold side! The a-line skirt creates a flirty silhouette while the faux leather panels add a hint of audacity to your style.
    $69.50
    $0.00
    $69.50
      13
    • Black
  • New
    Frayed Knitted BoleroFrayed Knitted Bolero

    Matching Set

    Frayed Knitted Bolero - Lush Meadow

    Boleros are far from basic when trimmed with frayed accents like our demure style layered over the matching maxi.
    $54.50
    $0.00
    $54.50
    Online Exclusive
      13
    • Lush Meadow
      • 63
    • Koi
  • New
    Geo Print Faux Wrap Maxi DressGeo Print Faux Wrap Maxi Dress

    Geo Print Faux Wrap Maxi Dress - Black Combo

    Geometric block shapes create an artful illusion print on this faux wrap maxi with a side slit to complete the sexy design.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      23
    • Black Combo
  • New
    Plus Size A Line Suede Dress Green Fit Flare DressPlus Size A Line Suede Dress Green Fit Flare Dress

    Faux Suede A Line Shirtdress - EDEN

    Faux suede done right. This shirtdress cinches at the waist with a belt and flares into an easy A-line shape that’s all about laid-back quiet luxury.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      83
    • EDEN
      • 93
    • Tan
  • New
    Plus Size Perforated Faux Leather DressPerforated Faux Leather Dress

    Perforated Faux Leather Dress - Lychee

    Make your presence known in our perforated faux leather dress. Whether you're attending a fashion event, a night out with friends or just want to express your individuality, this dress embodies the perfect blend of bold and feminine aesthetics. The flounced hem adds a...
    $89.50
    $0.00
    $89.50
    Online Exclusive
      23
    • Lychee
  • New
    Leopard Intarsia Sweater DressLeopard Intarsia Sweater Dress

    Leopard Intarsia Sweater Dress - Multi

    This colorful leopard sweater dress comes ready to stir things up. The knit hugs your shape, the pattern pops against the black background and the whole look serves fab energy.
    $74.50
    $0.00
    $74.50
      23
    • Multi
  • New
    Two Tone A Line Maxi DressTwo Tone A Line Maxi Dress

    Available in Lengths

    Two Tone A Line Maxi Dress - Black White

    A black textured maxi dances with contrast as a white paneled a-line skirt twirls against a balanced boat neck.  Available in regular and tall lengths.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      33
    • Black White
  • New
    Faux Leather DusterFaux Leather Duster

    Matching Set

    Faux Leather Duster - Black

    Faux leather duster is sexy & fun with an open front that slides over your look with ease. Layer it with the matching dress for a set that puts the "ooo" in ooolala!!!
    $64.50
    $0.00
    $64.50
      23
    • Black
  • New
    Plus Size Ruched Geo Print Bodycon DressRuched Geo Print Bodycon Dress

    Ruched Geo Print Bodycon Dress - Multi

    This dress does not play. Hugs with confidence, the ruched sides keep the fit fun & vibes high and the front cutout brings that flirty hit you can’t ignore. The geo print amps it up even more, turning a simple night out into a...
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Flounced Floral Sheath DressFlounced Floral Sheath Dress

    Flounced Floral Sheath Dress - Multi

    Blossoming all over, this floral-print sheath dress features a square neckline and a flounced hem that flutters.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • New
    Plus Size Lace Up Sharkbite Sweater DressLace Up Sharkbite Sweater Dress

    Lace Up Sharkbite Sweater Dress - Heather Grey

    This knitted mock-neck dress is loaded with personality-speaking features like the lace-up sleeves and sharkbite hem that are totally made for double taps & nonstop likes!
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Heather Grey
  • New
    Plus Size Pleated Sleeved A Line DressPleated Sleeved A Line Dress

    Pleated Sleeved A Line Dress - Pink Yarrow

    A little flounce & a little flirt, this stretch-crepe dress with pleated georgette sleeves and an A-line skirt was made for party season.
    $79.50
    $0.00
    $79.50
    Online Exclusive
      13
    • Pink Yarrow
  • New
    Faux Leather Bodycon Tank DressFaux Leather Bodycon Tank Dress

    Matching Set

    Faux Leather Bodycon Tank Dress - Black

    Our faux leather bodycon tank dress in sleek black is smooth, fitted and unapologetic. It pairs with the matching duster for a matching set that sparks energy but can be worn solo when you want the simply sexy style to shine.
    $64.50
    $0.00
    $64.50
      33
    • Black
  • New
    Floral Faux Wrap Maxi DressFloral Faux Wrap Maxi Dress

    Available in Lengths

    Floral Faux Wrap Maxi Dress - Black Combo

    This floral maxi drifts into daydream territory with a gently crossed neckline & an a-line skirt. Soft, stretchy and full of quiet romance, it’s the dress you reach for when you want your look to feel like a love note.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Black Combo

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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.