Sidebar

Color

Show more Show All

Size

Show more Show All

Price

$
to
$

Plus size Dresses Date Night

Filter
  • 10
  • 15
  • 20
  • 25
  • 30
  • 50
  • Featured
  • Best selling
  • Newest Arrivals
  • Price, low to high
  • Price, high to low
Sort

Sort by:

  • Featured
  • Best selling
  • Alphabetically, A-Z
  • Alphabetically, Z-A
  • Price, low to high
  • Price, high to low
  • New
    Belted Faux Wrap DressBelted Faux Wrap Dress

    Belted Faux Wrap Dress - BIKING RED

    Sash it up. This stretch-knit midi dress keeps things fun with a faux wrap neckline, flounced hem and swishy skirt that knows how to flirt. Elasticized cuffs give the sleeves a little volume and the tie waist pulls it all together just right.
    $64.50
    $0.00
    $64.50
      23
    • BIKING RED
      • 93
    • Dusk Blue
      • 173
    • Black
  • New
    Cape Effect Textured Sheath DressCape Effect Textured Sheath Dress

    Cape Effect Textured Sheath Dress - EDEN

    Make way for a textured-knit sheath that knows how to show off. The V-neck serves up just enough sass while cape-effect sleeves bring all the drama. Desk to dinner, it’s your power move in dress form.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • EDEN
      • 93
    • Lychee
      • 173
    • MAUVE WINE
  • New
    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
  • New
    Plus Size Bell Sleeved Swirl Print DressBell Sleeved Swirl Print Dress

    Bell Sleeved Swirl Print Dress - Multi

    Swirl into the spotlight in this textured-knit sheath dress with bell sleeves that are the drama we want! The curve-skimming fit keeps it sleek as the bold print makes sure all eyes stay on you.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Multi
  • New
    Plus Size Denim Print Bodycon DressDenim Print Bodycon Dress

    Denim Print Bodycon Dress - Denim Blue

    Denim print gets a sexy remix in this stretch-knit midi bodycon dress. Two daring slits at the sides let you flash just enough leg while the curve-hugging fit keeps all eyes where they should be.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Denim Blue
  • Ring Embellished Seamed DressRing Embellished Seamed Dress

    Ring Embellished Seamed Dress - Black

    This stretch-knit swing dress keeps it fun with ring accents and seam details that know how to stand out. Finished with an A-line hem that brings the swish, it’s your go-to for plans that call for a little extra.
    $59.50
    $0.00
    $59.50
      13
    • Black
      • 113
    • MOSS
  • New
    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
  • New
    Plus SizePrinted Bodycon DressPrinted Bodycon Dress

    Printed Bodycon Dress - Olive

    This printed stretch-knit bodycon hugs like it means it. The mock neck keeps things sleek up top while the curve-loving fit brings the heat from every angle.
    $59.50
    $0.00
    $59.50
      13
    • Olive
      • 63
    • Burgundy
  • New
    Plus Size Printed Wrap DressPrinted Wrap Dress

    Printed Wrap Dress - Black Combo

    Printed stretch-knit wrap dress with easygoing charm and a flirty finish. Tie it up and head out because cute comes easy.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Black Combo
  • New
    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
    Online Exclusive
      13
    • Nugget Gold
  • Plus Size Tank Bubble DressTank Bubble Dress

    Tank Bubble Dress - Black

    Stretch-knit up top keeps things fitted, while the poplin skirt brings the volume. Two side pockets mean you’ve got room for your essentials, and the elastic hem gives it that bounce with every step.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      43
    • Black
      • 93
    • White
  • New
    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
      33
    • Multi
  • New
    Plus Size Textured Tiered DressTextured Tiered Dress

    Textured Tiered Dress - Rose

    This textured-knit dress hugs you up top and flirts with a ruffled skirt that kicks with every step. The slip-on fit keeps things simple so you can throw it on and get straight to the fun.
    $64.50
    $0.00
    $64.50
      13
    • Rose
      • 63
    • Black
  • New
    Belted Off The Shoulder DressBelted Off The Shoulder Dress

    Belted Off The Shoulder Dress - Wine

    Bare those shoulders and let the compliments roll in. This off-the-shoulder stretch-crepe dress fits like it was made for you, cinches at the waist with flirty sash ties & slips on in seconds so you can get straight to the fun stuff.
    $64.50
    $0.00
    $64.50
      13
    • Wine
      • 63
    • Rust
      • 113
    • Dark Green
      • 163
    • Mustard
  • New
    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
    Online Exclusive
      23
    • Dark Citron
  • New
    Plus Size Chain Print Chain Trimmed DressChain Print Chain Trimmed Dress

    Chain Print Chain Trimmed Dress - Abundant Green

    Chain print meets chain-link straps in a crepe maxi made to show off. The faux wrap brings the shape, the A-line skirt brings the flow, and the cutout back with ties? Sexy & flowy.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      23
    • Abundant Green
  • New
    Plus Size Crocheted Trim Pompom DressCrocheted Trim Pompom Dress

    Crocheted Trim Pompom Dress - Black

    Light, floaty & full of fun, this chiffon dress goes all in with pom poms, shirred cuffs and crochet trims that add just the right touch of texture.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      23
    • Black
  • New
    Plus Size Pop Art Bodycon DressPop Art Bodycon Dress

    Pop Art Bodycon Dress - BIKING RED

    Pop art vibes upgrades the easy fit of our scuba bodycon dress. With a mock neckline that keeps things just right, this print-packed piece hugs your curves and serves up major fun.
    $64.50
    $0.00
    $64.50
      13
    • BIKING RED
  • New
    Plus Size A Line Dress Circle Print Maxi Dress Summer Fit Flare DressChain Trimmed Circle Print Dress

    Chain Trimmed Circle Print Dress - Multi

    This maxi goes all in on color with a rainbow circle print that steals the spotlight. The faux wrap neckline meets chain-link shoulder straps for a little shine up top. An A-line skirt flows with every step, and the sash-tie waist keeps things cinched....
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Multi
  • New
    Plus Size A Line Dress Geo Print Maxi Dress Summer Fit Flare DressChain Trimmed Geo Print Dress

    Chain Trimmed Geo Print Dress - Fandango Pink

    Shades of pink & green, cream & black all team up in a geo print that does everything right in the name of fashion. The faux wrap neck meets chain-link straps that takes the work out of matching accessories.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Fandango Pink
  • New
    Plus Size Cape Effect Geo Print DressCape Effect Geo Print Dress

    Cape Effect Geo Print Dress - Black Combo

    Green, black & white team up on our textured-knit sheath that’s anything but ordinary. Cape-effect sleeves bring the drama so every step feels like your runway.
    $69.50
    $0.00
    $69.50
    Online Exclusive
      13
    • Black Combo
  • Plus Size A Line Dress Floral Print Maxi Dress Summer Fit Flare DressChain Trimmed Floral Print Dress

    Chain Trimmed Floral Print Dress - Abundant Green

    Fresh-picked & twirl ready. This floral maxi brings the greens & blues in a flowy crepe silhouette with a faux wrap neck, chain-link shoulder straps and waist ties. The back cutout? Just a little something extra.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Abundant Green
  • New
    Plus Size A Line Dress Striped Summer Maxi Dress Fit Flare DressOmbre Striped Maxi Dress

    Ombre Striped Maxi Dress - Multi

    Sunset tones, served in stripes. This ombre maxi runs through pinks, reds and browns in a crepe fabric that flows with every step. 
    $64.50
    $0.00
    $64.50
    Online Exclusive
      23
    • Multi
  • New
    Plus Size Off The Shoulder Colorblock DressOff The Shoulder Colorblock Dress

    Off The Shoulder Colorblock Dress - Multi

    This off-the-shoulder cotton-blend maxi brings the soft summer energy in hues of white, cream and green. The elasticized bustline & puffed sleeves keep things sweet, the A-line skirt flows easy and side pockets are ready for whatever the day brings.
    $64.50
    $0.00
    $64.50
    Online Exclusive
      13
    • Multi
  • New
    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
    Online Exclusive
      13
    • Multi
  • New
    Plus Size Studded Stretch Knit Sheath DressStudded Stretch Knit Sheath Dress

    Studded Stretch Knit Sheath Dress - Black

    Our stretch-knit sheath dress keeps it sleek & chic with a boatneck and gold studs you can wear for afterwork meetups or to make a lasting impression on a first date.
    $69.50
    $0.00
    $69.50
      13
    • Black
  • New
    Crochet Trimmed Pompom DressCrochet Trimmed Pompom Dress

    Crochet Trimmed Pompom Dress - Navy Blazer

    Light, floaty & full of fun, this chiffon dress goes all in with pom poms, shirred cuffs and crochet trims that add just the right touch of texture.
    $74.50
    $0.00
    $74.50
    Online Exclusive
      33
    • Navy Blazer
  • New
    Cold Shoulder Maxi DressCold Shoulder Maxi Dress

    Cold Shoulder Maxi Dress - Rhododendron

    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
    Online Exclusive
      13
    • Rhododendron
      • 103
    • Nugget Gold
  • New
    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
    Online Exclusive
      13
    • Green

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.