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Plus size Dresses Date Night

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  • New
    Textured Cape Sheath DressTextured Cape Sheath Dress

    Textured Cape Sheath Dress - Lemon Drop

    Bursting with spring energy, this textured sheath dress features a V-neck, a back cutout and an attached cape that's chic & exciting.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Lemon Drop
      • 93
    • Calypso Coral
      • 173
    • Black
      • 253
    • White
  • New
    Off The Shoulder Polka Dot DressOff The Shoulder Polka Dot Dress

    Off The Shoulder Polka Dot Dress - White Black

    This off-the-shoulder maxi dress is made for sunny days and chic events. The foldover shoulder frames the neckline and the ribbed-knit bodice provides a fitted, comfortable fit. A polka dot woven skirt is relaxed and chic giving lightness to the pep in your step.
    $74.50
    $0.00
    $74.50
      13
    • White Black
  • New
    Plus Size Floral Swing Dress Flower Print Neck Ties Summer DressTie Neck Floral Print Dress

    Tie Neck Floral Print Dress - Multi

    Fresh florals and an airy silhouette make this dress an easy summer pick. Neckties at the keyhole add a sweet detail you can style your way, from loose and relaxed to softly tied.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • New
    Plus Size Checked Blue Textured Knit Midi Skirt Three Piece SetChecked Textured Knit Tank

    Matching Set

    Checked Textured Knit Tank - POWDER BLUE

    Soft texture, reimagined checks. This tank is a fabulous base for any look. Try yours own with a pair of jean or match yours up with the cardigan and skirt for a coordinated set.
    $29.50
    $0.00
    $29.50
      13
    • POWDER BLUE
  • New
    Plus Size Midaxi Dress Plus Size Formal Cape Gown Luxe DressOff The Shoulder Cape Dress

    Off The Shoulder Cape Dress - Bridal Rose

    This off-the-shoulder midaxi dress is striking and elegant. The foldover neckline highlights the shoulders revealing a collarbone-baring look. A sheer mesh cape drapes from the back creating dramatic movement.
    $89.50
    $0.00
    $89.50
    Online Exclusive
      33
    • Bridal Rose
      • 173
    • Black
      • 333
    • Amazon
  • New
    Plus Size Checked Blue Textured Knit Midi Skirt Three Piece SetChecked Textured Midi Skirt

    Matching Set

    Checked Textured Midi Skirt - POWDER BLUE

    Our soft midi has the perfect easy drape. This checked textured-knit skirt can be worn with your fave separates or pair with the matching tank & cardigan for a complete three-piece set.
    $49.50
    $0.00
    $49.50
      13
    • POWDER BLUE
  • New
    Plus Size Checked Blue Textured Knit Cardigan Three Piece Matching SetChecked Textured Knit Cardigan

    Matching Set

    Checked Textured Knit Cardigan - POWDER BLUE

    Light layers, spring style. This checked textured-knit cardigan finishes any look and pairs with the matching tank and skirt for an easy three-piece set.
    $59.50
    $0.00
    $59.50
      13
    • POWDER BLUE
  • New
    Chain Trimmed Wave Print DressChain Trimmed Wave Print Dress

    Chain Trimmed Wave Print Dress - Victoria Blue

    This wavy print satin maxi flows in shades of blue like sunlight on water. Chain-link shoulder straps add a dose of bejeweled excitement while the fluid silhouette drapes beautifully.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Victoria Blue
  • New
    Plus Size Ruffle Short Sleeve Babydoll Watercolor Dress Sun 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
      13
    • Multi
  • New
    Strapless Rosette A Line DressStrapless Rosette A Line Dress

    Strapless Rosette A Line Dress - Yellow

    Whether you're a vision in yellow or wow in white, stunning is your new name in our mesh dress. Covered head to toe in lush rosettes, it hugs you just right through the bodice before flaring into a flirt-ready A-line skirt.
    $109.50
    $0.00
    $109.50
    Online Exclusive
      13
    • Yellow
      • 93
    • White
  • New
    Printed Off The Shoulder DressPrinted Off The Shoulder Dress

    Printed Off The Shoulder Dress - Multi

    Like a scene out of a romantic dream, you are a vision of beauty & sultriness dripped in our off-the-shoulder maxi with a bit of built-in flirtation thanks to the flounce overlay & bodycon fit.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • New
    Off The Shoulder Polka Dot DressTall Off The Shoulder Polka Dot Dress

    Available in Lengths

    Tall Off The Shoulder Polka Dot Dress - White Black

    This off-the-shoulder maxi dress is made for sunny days and chic events. The foldover shoulder frames the neckline and the ribbed-knit bodice provides a fitted, comfortable fit. A polka dot woven skirt is relaxed and chic giving lightness to the pep in your step.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • White Black
  • New
    Plus Size White Wide Leg Jumpsuit Party Strapless One Piece JumpsuitCutout Fringed Jumpsuit

    Cutout Fringed Jumpsuit - White

    One piece, full impact. This wide-leg jumpsuit brings a high neckline and a fringed cutout overlay that shows up & shows out!
    $79.50
    $0.00
    $79.50
      13
    • White
  • New
    Printed Off The Shoulder DressTall Printed Off The Shoulder Dress

    Available in Lengths

    Tall Printed Off The Shoulder Dress - Multi

    Like a scene out of a romantic dream, you are a vision of beauty & sultriness dripped in our off-the-shoulder maxi with a bit of built-in flirtation thanks to the flounce overlay & bodycon fit.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Belted Scarf Print Maxi DressBelted Scarf Print Maxi Dress

    Belted Scarf Print Maxi Dress - Multi

    This scarf print crepe maxi swirls of rainbow hues that feel like vacation in motion. A softly gathered neckline adds a touch of ease with the sash-tie waist so you can wear it your way.
    $69.50
    $0.00
    $69.50
      13
    • Multi
  • New
    Pleated Sleeve Tropical Wrap DressPleated Sleeve Tropical Wrap Dress

    Available in Lengths

    Pleated Sleeve Tropical Wrap Dress - Persimmon Orange

    Island mood, elevated. This tropical print maxi wrap dress features airy pleated chiffon sleeves and tie-fastenings at the waist that feels vibrant, feminine and ready for summer fun.
    $69.50
    $0.00
    $69.50
      13
    • Persimmon Orange
  • New
    Textured Knit Checked TankTextured Knit Checked Tank

    Matching Set

    Textured Knit Checked Tank - Apple Green

    Soft texture, reimagined checks. This tank is a fabulous base for any look. Try yours own with a pair of jean or match yours up with the cardigan and skirt for a coordinated set.
    $29.50
    $0.00
    $29.50
    Online Exclusive
      13
    • Apple Green
  • New
    Fringed Cutout JumpsuitFringed Cutout Jumpsuit

    Fringed Cutout Jumpsuit - Green

    One piece, full impact. This wide-leg jumpsuit brings a high neckline and a fringed cutout overlay that shows up & shows out!
    $79.50
    $0.00
    $79.50
    Online Exclusive
      13
    • Green
  • New
    Tropical Off The Shoulder DressTropical Off The Shoulder Dress

    Tropical Off The Shoulder Dress - Black Combo

    Island allure, this off-the-shoulder tropical print maxi dress features ruched detailing along and a subtle split along the sides creating a sexy fitted cut that feels vibrant and feminine.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      33
    • Black Combo
  • New
    Plus Size Maxi Dress Green Infinity Dress Multi Way DressConvertible Multi Way Dress

    Convertible Multi Way Dress - Green

    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
    • Green
  • New
    Plus Size Tropical Print Split Drama Sleeve Party Summer Maxi DressSplit Sleeve Tropical Print Dress

    Split Sleeve Tropical Print Dress - Persimmon Orange

    A little paradise with pops of bodacious deliciousness. This tropical print maxi dress features a flattering faux wrap neck, dramatic crepe sleeve panels with splits of sexy and a bonus front split.
    $69.50
    $0.00
    $69.50
      13
    • Persimmon Orange
  • New
    Rosette Crochet Maxi DressRosette Crochet Maxi Dress

    Rosette Crochet Maxi Dress - Natural

    This crochet-knit maxi dress is perfect for sun-filled escapes. Delicate rosettes increase the sensual romance of the peek-of-skin design. A side split and tie-fastening open back bring sexiness from the beach to the after hours.
    $74.50
    $0.00
    $74.50
      33
    • Natural
      • 113
    • Black
  • New
    Textured Knit Checked CardiganTextured Knit Checked Cardigan

    Matching Set

    Textured Knit Checked Cardigan - Apple Green

    Light layers, spring style. This checked textured-knit cardigan finishes any look and pairs with the matching tank and skirt for an easy three-piece set.
    $59.50
    $0.00
    $59.50
    Online Exclusive
      13
    • Apple Green
  • New
    Faux Wrap Wide Leg JumpsuitFaux Wrap Wide Leg Jumpsuit

    Faux Wrap Wide Leg Jumpsuit - Amazon

    Waist tied, energy set. This wide-leg jumpsuit features a faux wrap neckline and sash ties that's sharp & chic.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Amazon
      • 93
    • Beetroot Purple
  • New
    Textured Checked Midi SkirtTextured Checked Midi Skirt

    Matching Set

    Textured Checked Midi Skirt - Apple Green

    Our soft midi has the perfect easy drape. This checked textured-knit skirt can be worn with your fave separates or pair with the matching tank & cardigan for a complete three-piece set.
    $49.50
    $0.00
    $49.50
    Online Exclusive
      13
    • Apple Green
  • New
    Ruched Swirl Print Maxi DressRuched Swirl Print Maxi Dress

    Available in Lengths

    Ruched Swirl Print Maxi Dress - Multi

    Swerve into the fast lane in our short-sleeved bodycon maxi. The swirl print is electrifying with a spicy split and cleverly placed ruching that enhances your curves while you stun.
    $69.50
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Embellished Cutout Bodycon DressEmbellished Cutout Bodycon Dress

    Embellished Cutout Bodycon Dress - Caribbean Sea

    You don't just enter the room, you own it. Our curve-hugging maxi drapes like a second skin, finished with sculptural wood and marble rings that kiss the shoulders. The hem is designed in fringe made from daring circle cutouts move with every step, every...
    $74.50
    $0.00
    $74.50
      13
    • Caribbean Sea
  • New
    Multi Way Convertible Maxi DressMulti Way Convertible Maxi Dress

    Multi Way Convertible Maxi Dress - Light Pastel Purple

    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 Purple
  • New
    Ombre Off The Shoulder Maxi DressOmbre Off The Shoulder Maxi Dress

    Ombre Off The Shoulder Maxi Dress - Persimmon Orange

    Sunset shades melt into this off-the-shoulder maxi made to steal the scene. A sweep of car wash splits shows a tinch of leg with every step turning soft movement into pure main character energy.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Persimmon Orange
  • New
    Off The Shoulder Ombre Maxi DressOff The Shoulder Ombre Maxi Dress

    Off The Shoulder Ombre Maxi Dress - Caribbean Sea

    Tropical tones melt from vivid yellow into lush greens & deep blues in this off-the-shoulder maxi. Car wash splits reveal just a tinch of leg with every step bringing fluid, island-night energy.
    $69.50
    $0.00
    $69.50
      13
    • Caribbean Sea

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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.