Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Look So Sweet Floral Applique Skater Party Dress
Effortlessly steal the show in this skater party dress at graduations or showers! Made with organza sheer fabric and adorned with delicate floral applique, this dress is sure to turn heads and make you feel like the belle of the ball. Designed with a flattering square neckline and adjustable spaghetti straps, the skater silhouette and short-length hem exude flirty charm so everyone will fall for you! Complete the look in strappy platform heels.
Fit & Features
- Floral appliques
- Sheer organza fabric with woven lining
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3084
Category Name: Casual Dresses
Price: $56.90
Availability: Out of Stock
Product Badge:- Sale
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Compliment Collector Corset Eyelet Skater Dress
You'll be collecting all the compliments in this heart eyelet skater dress perfect for brides-to-be, birthday girlies, and graduates! This playful dress features puff short sleeves, a sweetheart neckline, and a corset bodice with flexible boning for a flattering fit. The skater silhouette and short-length hem make it perfect for any occasion. Complete the look in wedge sandals.
Fit & Features
- Eyelet heart pattern fabric, woven lining
- Sweetheart neckline
- Flexible boning
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3080
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Covetable Charm Strapless Mini Skater Dress
From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.
Fit & Features
- Poplin stretchy fabric, sewn-in knit lining
- Back zipper and hook-eye closure
- Strapless square neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3079
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ray Of Beauty Lace-Up Corset Skater Dress
You'll be a ray of beauty in this chic lace-up corset skater dress! Designed with a lightweight woven fabric with a stretchy knit lining, this adorable short dress captures the summer season. It features an alluring sleeveless corset-style bodice with a ruched sweetheart neckline and a tie-front detail at the bust. The thin adjustable tank straps lead to a lace-up strappy back design to find your perfect fit. The angled high waist seam flows out to a fit-and-flare skater silhouette with pleating for a flirtatious vibe. Complete the look with platform heels!
Fit & Features
- Cotton woven fabric, stretchy knit lining
- Corset-style bodice, ruched sweetheart neckline, tie-front bust
- Thin adjustable tank straps
- Lace-up strappy back, tie closure
- Side zipper with hook and eye closure
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3641
Category Name: Casual Dresses
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picturesque Cutie Corset Lace-Up A-Line Midi Dress
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.
Fit & Features
- Woven fabric lined with stretchy knit
- Sweetheart neckline, tie-front detail
- Thin adjustable straps
- Corset bodice, lace-up back
- High waist seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3069
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Days Off Scoop Neck Smocked Skater Dress
Grab your favorite sunnies cause it's time to take a sunny stroll in this skater dress down by the beach or to the coffee shop! With adjustable straps and a stretchy smocked bust, this dress provides the perfect fit every time. The playful ruffled skater silhouette and short-length hem make it a must-have for any sunny day. Complete the look with strappy sandals.
Fit & Features
- Airy woven fabric with woven lining
- Adjustable spaghetti straps
- Scoop neckline
- Stretchy smocked bust
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5462
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Patchwork It Belted Denim Mini Dress
Elevate your style with this patchwork denim mini dress! Featuring a flattering square neckline, spaghetti straps, and a bodycon silhouette, this dress will hug your curves in all the right places. The exposed front zipper closure and flap pockets add a modern touch, while the adjustable waist belt cinches your waist for a perfect fit. Complete the look with platform heels for a daytime party!
Fit & Features
- Patchwork design
- Non-stretch denim fabric
- Exposed front zipper closure
- Adjustable waist belt
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5459
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tea Time Ruffled Short Skater Dress
It's time for afternoon tea and this skater dress will make an adorable entrance! Get ready to sashay in this dress featuring a ruffle trim square neckline and tiered ruffled short-length hem to add a playful touch to the skater silhouette. And with adjustable spaghetti straps and a stretchy smocked bodice, you'll be comfortable all day. Complete the look in chic wedges and a flouncy hat.
Fit & Features
- Woven fabric lined with woven fabric
- Ruffle trim neckline
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Tiered ruffled short-length hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3059
Category Name: Casual Dresses
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Appeal Sleeveless Ruffled Midi Dress
You'll always give off a darling appeal in this sleeveless midi dress for casual occasions! With a classic square neckline and dual spaghetti straps, this dress is perfect for any occasion. The stretchy smocked bodice ensures a comfortable fit while the A-line silhouette and ruffled midi-length hem add a flattering touch. Complete the look in sandals and a crossbody bag.
Fit & Features
- Woven fabric, no stretch
- Square neckline
- Dual spaghetti straps
- Stretchy smocked bodice
- A-Line ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5457
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Style Puff Sleeve Chiffon Skater Dress
Create the sweetest charming style for your spring and summer parties in this chiffon skater dress! The airy sheer chiffon fabric offers that breezy lightweight feel and includes a stretchy knit lining for coverage. The short dress features a ruched square neckline, adorable short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette for a flirty vibe with a ruffled hem. Pair with sneakers for a cute and casual look!
Fit & Features
- Sheer chiffon fabric with stretchy knit lining
- Ruched square neckline
- Short puff sleeves with elasticized hems
- High waist seams, back zipper with hook and eye closure
- Skater silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3056
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delightfully Chic Ruffled Floral Chiffon Midi Dress
Create a delightfully chic outfit for weekend parties in this airy floral chiffon midi dress! Designed with a lightweight sheer chiffon fabric with a lining for coverage, this mid-length dress is accented with a blooming rose print in subtle hues for a simply gorgeous look. It features a square neckline, adjustable spaghetti straps with dainty ruffled accents, a fitted high waist, and a flowy A-line silhouette detailed with a high front slit and feminine ruffled hem. Complete the look with hoop earrings.
Fit & Features
- Rose-printed chiffon fabric, stretchy knit lining
- Square neckline
- Adjustable spaghetti straps with ruffled accents
- High waist, back zipper with hook-eye closure
- A-line fit
- Front slit, ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3046
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiate Romantic Vibes Strapless Floral Chiffon Maxi Dress
Radiate romantic vibes in this strapless floral chiffon maxi dress at garden parties or showers! The long ruffled silhouette adds flow and movement while the floral chiffon fabric adds a touch of femininity. Perfect for any occasion, this dress will make you stand out with its playful and flirty style! Complete the look with teardrop earrings.
Fit & Features
- Floral printed chiffon fabric with stretchy knit lining
- Strapless neckline
- Back zipper and hook-eye closure
- Ruffled flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3044
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Charm Off-The-Shoulder Floral Mesh Mini Dress
Showcase your sweet charm at spring and summer parties in this floral mesh mini dress! The airy sheer mesh fabric is accented with a dainty floral print for the prettiest vibe and includes a full-length knit lining for coverage. The off-the-shoulder sweetheart neckline gives the dress a feminine touch, and features sheer short-sleeved cuffs and a V-cut bust design with a tie-front detail. The ruching down the side seams will accentuate your gorgeous curves along the bodycon silhouette. Style this adorable mini dress with clear heels.
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Floral print
- Off-the-shoulder sweetheart neckline, short sleeve cuffs
- V-cut bust design with tie-front detail
- Ruched bust and side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3050
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Angelic Beauty Strapless Printed Mesh Midi Dress
Showcase your angelic beauty in this strapless printed mesh midi dress! The stretchy sheer mesh fabric features an angel cherub multi-print pattern for a celestial vibe, and includes a knit lining for coverage. The bodice is shaped with a strapless elasticized straight neckline, leading to ruching down the back and side seams to accentuate your gorgeous curves on the bodycon silhouette. The mid-length hem is accented with a back slit for a chic detail and added movement. Style with knee-high boots for date night.
Fit & Features
- Stretchy sheer mesh fabric, knit lining
- Angel cherub multi-print pattern
- Strapless elasticized straight neckline
- Ruched back and side seams
- Back slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3051
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Vibe Tie-Back Flowy Floral Woven Maxi Dress
Give off a charming vibe at summer parties in this simply stunning floral woven maxi dress! The breezy lightweight woven fabric is detailed with a gorgeous floral print pattern and includes a mini-length lining for coverage. The sleeveless bodice is shaped with a sweetheart neckline, a dainty tie-front bust design for a cute detail, and spaghetti straps leading to an open back with a cross-back strappy design and a customized tie closure. The fitted high waist flows out to a maxi-length hem with an effortlessly chic A-line silhouette. Style with hoop earrings and slip-on sandals.
Fit & Features
- Floral print
- Lightweight woven fabric, mini-length woven lining, no stretch
- Sweetheart neckline with tie-front bust, spaghetti straps
- Open back, cross-back strappy design, tie closure
- High waist seam
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3048
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Beauty Puff Sleeve Floral Chiffon Midi Dress
This breezy floral chiffon midi dress will forever be a beautiful style for bridal showers, parties, and brunches! The airy sheer chiffon fabric is accented with a dainty floral print for a soft feminine vibe and includes a knit lining for coverage. The mid-length dress features a ruched square neckline detailed with a keyhole cutout and tie-front design, adorable short puff sleeves with elastic cinched hems, fitted high waist seams, and a chic high front slit for added movement on the flowy A-line silhouette. Complete the look with heels.
Fit & Features
- Floral print
- Sheer chiffon fabric with stretchy knit lining
- Ruched square neckline, keyhole cutout with tie-front
- Short puff sleeves, back zipper with hook and eye closure
- High front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3033
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crush-Worthy Strapless Denim Bodycon Midi Dress
They'll all be crushing on you in the cutest denim bodycon midi dress! The cotton-blend denim fabric offers stretch and includes a comfy knit lining. This dress is shaped with a strapless scoop neckline featuring an angled design to accentuate your bust, with flexible boning at the bodice giving structure for a snatched look. The vertical seams down the front and back add a trendy touch to the curve-hugging silhouette. The back slit accent adds a sexy detail and allows for effortless movement. Style with a layered necklace and clear heels for your weekend plans!
Fit & Features
- Cotton-blend denim fabric with knit lining, moderate stretch
- Strapless angled scoop neckline
- Flexible boning
- Back zipper with hook and eye closure
- Back slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5453
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Style Puff Sleeve Floral Chiffon Skater Dress
Show off the sweetest style in this breezy floral chiffon skater dress! The airy sheer chiffon fabric is detailed with an adorable dainty floral print for a charming vibe. The short dress features a square neckline with ruching and a small tie-front detail, short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette. Style with espadrille wedges for weekend brunch!
Fit & Features
- Sheer chiffon fabric, stretchy knit lining
- Dainty floral print
- Ruched square neckline, tie-front detail
- Short puff sleeves
- High waist seams, back zipper with hook and eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3027
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Speechless Strapless Floral Ruffle Mini Dress
Leave everyone speechless when you stroll in wearing this floral mini dress at parties or brunch! The strapless neckline and stretchy smocked bodice provide a comfortable and flattering fit, while the dainty floral print and embroidery add a touch of whimsy. Complete the look with sunnies.
Fit & Features
- Dainty floral print and embroidery
- Woven fabric, some stretch
- Fitted silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5456
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty-Chic Lace-Trim Woven Corset Skater Dress
This adorable lace-trim woven corset skater dress will bring a dainty-chic style to your party look. The sheer stretch woven fabric offers an airy, lightweight feel with a knit lining for coverage. The short dress features a square neckline with a scalloped lace trim and sheer lace cap sleeves for the prettiest detail. The ruched bust leads to a corset front with a lace-up design for a snatched look. The high waist flows out to a skater skirt with a fit and flare silhouette. Complete your outfit with rhinestone heels for that pop of sparkle.
Fit & Features
- Sheer stretch woven fabric with knit lining
- Square neckline with scalloped lace trim
- Sheer scalloped lace cap sleeves
- Ruched bust, corset bodice with lace-up front
- Back zipper, hook and eye closure
- High waist seam, skater skirt with fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3026
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Subtle Charm V-Neck Ruffled Floral Skater Dress
Embrace your inner charm in this floral skater dress at showers or birthdays! The flattering V-neckline and adjustable spaghetti straps provide a perfect fit, while the tiered ruffled skater silhouette adds a touch of feminine flair. With its tie-back design, short-length hem and beautiful floral print, this dress will make you feel effortlessly stylish. Complete the look in mules and earrings!
Fit & Features
- Ditsy floral print
- Chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Tiered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3022
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Look Ditsy Floral Chiffon Babydoll Dress
Create the sweetest look for your summer plans with this adorable babydoll dress! The airy sheer chiffon fabric is detailed with a ditsy floral print and includes a full-length lining for coverage. The short dress features a sleeveless scoop neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a ruffled tiered A-line silhouette with an effortless flowy fit. Style with sneakers for a cute and casual summer outfit.
Fit & Features
- Ditsy floral print
- Sheer chiffon fabric with stretchy knit lining
- Ruched scoop neckline
- Adjustable spaghetti straps
- Smocked back
- Ruffled tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5451
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Chic Floral Embroidered Chiffon Skater Dress
This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.
Fit & Features
- Sheer embroidered chiffon fabric, floral print, stretchy knit lining
- Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
- Adjustable spaghetti straps
- Partial stretchy smocked back, zipper with hook and eye closure
- Front faux buttons, high waist seam
- Fit and flare A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3009
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Sale