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Plus size Dresses Date Night

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  • 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
    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
    Plus Size Maxi Dress Blush Pink Infinity Dress Multi Way DressConvertible Multi Way Maxi Dress

    Convertible Multi Way Maxi Dress - Blush

    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
    • Blush
  • 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
    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
    Plus Size Maxi Dress Plus Size Floral Dress Flowers Summer DressChain Trimmed Floral Maxi Dress

    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
      13
    • Primrose Yellow
  • New
    Leopard Denim Midi DressLeopard Denim Midi Dress

    Leopard Denim Midi Dress - Black Animal

    Denim goes wild in the design of our leopard print midi featuring cap sleeves, button detailing and a front split that reminds everyone who's the star of the show.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • Black Animal
  • 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 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 sheath dress plus size church dress plus midaxi knit dressColorblock Midaxi Sheath Dress

    Colorblock Midaxi Sheath Dress - Black Combo

    A minimalist take on the classically chic dress, we elevate the style with the midaxi length and panels of neutral colors.
    $49.50
    $0.00
    $49.50
      13
    • Black Combo
  • 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
      73
    • 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
    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
    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 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 Lemon Cotton Sun Dress Maxi Off The Shoulder Summer DressOff The Shoulder Lemon Print Dress

    Off The Shoulder Lemon Print Dress - Victoria Blue

    Bare shoulders & a juicy lemon print lead the way on this off-the-shoulder maxi. A shirred bustline hugs close, sash ties define the waist and a flounced hem keeps things looking freshly squeezed.
    $69.50
    $0.00
    $69.50
      13
    • Victoria Blue
  • 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
    • Black
      • 173
    • Calypso Coral
      • 253
    • White
  • 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
    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
    Leopard Denim Midi DressTall Leopard Denim Midi Dress

    Tall Leopard Denim Midi Dress - Black Animal

    Denim goes wild in the design of our leopard print midi featuring cap sleeves, button detailing and a front split that reminds everyone who's the star of the show.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      13
    • Black Animal
  • New
    Plus Size Wide Leg Jumpsuit Summer Sleeveless Woven JumpsuitWoven Wide Leg Jumpsuit

    Woven Wide Leg Jumpsuit - Caribbean Sea

    Low-key and warm-weather approved, this woven wide-leg jumpsuit keeps it simple with a clean V-neck and adjustable straps for a perfect fit.
    $49.50
    $0.00
    $49.50
      13
    • Caribbean Sea
      • 93
    • Olive Night
  • 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
    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
    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 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
    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 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
    Denim Midi Tube DressDenim Midi Tube Dress

    Matching Set

    Denim Midi Tube Dress - Denim

    Say hey to our midi tube dress that curves over your curves and holds its nerve then breaks into a sexy side split. It’s not trying to be sweet or safe, it’s here to be noticed. Wear it solo when you want the stare,...
    $64.50
    $0.00
    $64.50
      13
    • Denim
  • 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 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

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.