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Plus size Dresses Date Night

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  • 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
      13
    • Multi
  • New
    Off The Shoulder Cape DressOff The Shoulder Cape Dress

    Off The Shoulder Cape Dress - Black

    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
      13
    • Black
      • 213
    • Bridal Rose
      • 333
    • Amazon
  • New
    Plus Size Textured Cape Sheath Dress Spring Summer Knit Shift DressTextured Cape Sheath Dress

    Textured Cape Sheath Dress - Black

    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
    • Black
      • 93
    • Lemon Drop
      • 173
    • Calypso Coral
      • 253
    • White
  • Status Print Maxi DressTall Status Print Maxi Dress

    Available in Lengths

    Tall Status Print Maxi Dress - PETUNIA

    Command the room. This status print maxi dress brings drama with a deep V-neck, knotted front & daring split. Oversized internal shoulder pads give a bold, structured finish that’s pure statement. Available in regular and tall lengths.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      73
    • PETUNIA
  • Bandana Print ShirtdressBandana Print Shirtdress

    Bandana Print Shirtdress - POWDER BLUE

    $64.50
    $0.00
    $64.50
      63
    • POWDER BLUE
  • 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 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
    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 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 Satin Yellow Halter Neck Sleeveless Party Matching Fashion SetEmbellished Satin Halter Top

    Matching Set

    Embellished Satin Halter Top - Spectra Yellow

    This is the top you reach for when the night calls. Satin halter, cowl neckline, gathered sides, and a gold-tone accent. Matching balloon pants take the entire look to the top.
    $49.50
    $49.50
      13
    • Spectra Yellow
  • 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
    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
    Plus Size Dark Wash Denim Dress Jean Dress Hi Low Handkerchief DressDenim Handkerchief Dress

    Denim Handkerchief Dress - Denim

    Denim gets a lighter feel with this V-neck dress and its easy handkerchief hem. Relaxed, flattering and made to move with you from day plans to happy hour fun.
    $69.50
    $0.00
    $69.50
      13
    • Denim
  • New
    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
    $0.00
    $69.50
      13
    • Calypso Coral
      • 93
    • Canary Yellow
  • New
    Plus Size Maxi Dress Plus Size Floral Dress Flowers Summer DressTall Chain Trimmed Floral Maxi Dress

    Available in Lengths

    Tall 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
    Online Exclusive
      13
    • Primrose Yellow
  • 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 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
    Keyhole Floral Print Midi DressKeyhole Floral Print Midi Dress

    Keyhole Floral Print Midi Dress - Papaya

    Retro blooms & citrus hues bring a little 70s daydream to this flowy georgette midi. A flirty keyhole detail and easy elastic waist keep it light, effortless. and ready for fun-filled plans.
    $49.50
    $0.00
    $49.50
      13
    • Papaya
  • 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 sheath dress plus size tulle dress trendy church dressTiered Tulle Sheath Dress

    Tiered Tulle Sheath Dress - Maize

    Showcase your Sunday Best in our textured-knit sheath dress constructed with a decollete-framing faux wrap and tiers of point d'esprit tulle.
    $54.50
    $0.00
    $54.50
      13
    • Maize
      • 63
    • Beetroot Purple
  • New
    Plus Size Dress A Line Little Black Dress Fit Flare Dress Knit DressTextured Knit A Line Dress

    Textured Knit A Line Dress - Black

    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
    Online Exclusive
      13
    • Black
  • 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
  • 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
    Plus Size Dress A Line Little Blue Dress Fit Flare Dress Knit DressEmbellished A Line Dress

    Embellished A Line Dress - Victoria Blue

    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
    • Victoria Blue
      • 93
    • Calypso Coral
  • 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
    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
    $0.00
    $69.50
      13
    • Canary Yellow
      • 93
    • White
  • New
    Ribbed Maxi Bodycon DressRibbed Maxi Bodycon Dress

    Ribbed Maxi Bodycon Dress - Raspberry Radiance

    Ribbed and curve-hugging, this maxi bodycon dress features a bustier top with padded cups and a front split that flaunts & teases.
    $59.50
    $0.00
    $59.50
    Online Exclusive
      13
    • Raspberry Radiance
      • 63
    • Bright Yellow
  • 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
    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
  • New
    Textured Denim Babydoll DressTextured Denim Babydoll Dress

    Textured Denim Babydoll Dress - Denim

    Sweet with a taste of 'tude. This textured-denim babydoll dress features a striped-trim V neck, soft ruffled sleeves & a flounced hem with just the right bounce.
    $69.50
    $0.00
    $69.50
      13
    • Denim

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.