Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

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Everyday Ease: Casual Dresses for Cool-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in burgundy or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • Chic Contrast Tube Mini Dress

    Sophisticated yet flirty, this strapless mini dress turns heads with its fitted bodice and pleated skirt. Add heels and jewelry for lunch in the city or a chic wine bar with the girls!

    Fit & Features

    • Woven fabric, contrast design
    • Tube strapless neckline
    • Fitted bodice
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5913

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Modern Babe Sleeveless Belted Mini Dress

    Take the city streets by storm in this sleeveless mini dress with a chic belted waist that cinches your look together from office hours to cocktail hour!

    Fit & Features

    • Woven fabric with stretch
    • Crew neckline
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Dual faux leather belted waist
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5979

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Chic Strapless Ribbed Knit Midi Dress

    Simply chic, this strapless ribbed knit midi dress is a closet staple. The asymmetric seams and form-hugging silhouette will show off your gorgeous curves.

    Fit & Features

    • Ribbed hacci knit fabric with knit lining, high stretch
    • Strapless straight neckline
    • Asymmetric seams
    • Midi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5956

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Jeanius Strapless Denim Mini Dress

    You're kind of a genius for showing off this strapless denim mini dress everywhere you go! Set the trend in this short dress with a classic jean style with belt loop accents and a flattering bodycon fit.

    Fit & Features

    • Denim fabric
    • Strapless neckline with belt loop accents
    • Jean-style design
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5936

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Polished Demure Belted Pleated Skater Dress

    A pretty and polished sleeveless skater dress designed with a tiered pleated mini skirt and a sleek faux leather belt that cinches the look together. 

    Fit & Features

    • Woven fabric
    • Sleeveless crew neckline
    • Back zipper and hook-eye closure
    • Faux leather belt
    • Skater silhouette
    • Tiered pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5971

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Day To Night Strapless Abstract Slit Maxi Dress

    From day to night, this strapless abstract print maxi dress is an effortless style for any plans!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5905

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Ease Cap Sleeve Cutout Midi Dress

    This cap sleeve midi dress is ready to elevate any casual day look to a cute level! Designed in a flattering bodycon silhouette, this dress boasts a flirty cutout back and a back slit for effortless movement. 

    Fit & Features

    • Stretchy rib knit fabric
    • Cap sleeves
    • Scoop neck
    • Cutout back
    • Center back slit
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5908

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed Sweetness Lace-Up Floral Skater Dress

    Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.

    Fit & Features

    • Floral print, woven fabric, bust lining
    • V-neckline, wide shoulder straps, padded bra cups
    • Lace-up back
    • Ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5622

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce Instinct Lace-Up Romper

    Unleash your wild side—this lace-up romper stuns with its bold animal print and flirty tiered skirt. The fitted bodice and strappy details keep the look daring, playful, and perfect for a night out.

    Fit & Features

    • Animal print, knit fabric
    • Sweetheart neckline with lace-up front
    • Adjustable spaghetti straps
    • Tiered mini skirt with flared hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000201

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

    Product Badge:
    • Best Seller
  • Popular Poise Mock Neck Abstract Mini Dress

    An abstract print mini dress features sheer fitted long sleeves, a mock neckline, and a flattering bodycon fit. Perfect for styling with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Mock neckline
    • Fitted sheer long sleeves
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5581

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always A Good Time Long Sleeve Midi Dress

    A basic midi dress every fashionista needs to create bold looks. The dress features side ruched seams and a bodycon silhouette to accentuate your curves while the midi-length hem makes it perfect for styling with boots or heels. 

    Fit & Features

    • Rib knit fabric, stretchy knit lining
    • Fitted long sleeves
    • Square neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5940

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Style Ribbed Knit Off-Shoulder Midi Dress

    Minimal effort, major effect. This off-shoulder ribbed knit midi dress is your go-to for sleek confidence with a side of chic style. Pairs perfectly with a red lip and your best “don’t need to try” attitude.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Asymmetric off-shoulder neckline, fold-over design
    • Long fitted sleeves
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5919

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Major Charmer Ditsy Floral Strapless Mini Dress

    Charm them with your adorable style in this lined eyelet knit mini dress with the cutest ditsy floral print. The form-hugging fit will highlight your curves.

    Fit & Features

    • Sheer eyelet knit fabric with knit lining, high stretch
    • Ditsy floral print
    • Strapless straight neckline
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6046

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trend Moment Denim Belted Pleat Mini Dress

    Hit the streets in this of-the-moment denim mini dress with a trendy belted design and flirty pleated hem!

    Fit & Features

    • Denim fabric, moderate stretch
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Belted design
    • Bodycon fit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5944

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crush On You Sleeveless V-Neck Skater Dress

    Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.

    Fit & Features

    • Gauze woven fabric lined with stretchy knit
    • Adjustable drawstring shoulder straps
    • V-Neckline and back
    • Fitted waist, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5500

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Nights Halter Slit Maxi Dress

    Glam meets wild in this sultry halter maxi dress. With its curve-hugging fit, statement hardware, and bold slit, it’s made for spotlight entrances and after-dark drama.

    Fit & Features

    • Animal print, knit-lined fabric with stretch
    • Halter neckline, hardware insert, spaghetti strap tie
    • Bodice cutout with hardware insert
    • High front slit
    • Form-hugging silhouette, maxi hem
    • Runs true to size

    Style Number/Barcode: 05102-000294

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Basic Cutie Long Sleeve Knit Midi Dress

    The perfect cute and basic midi dress for all of your styling needs! The dress is designed with a flattering square neckline that shapes the form-hugging fit and flattering midi-length hem. Pair with a dainty necklace.

    Fit & Features

    • Stretchy rib knit fabric
    • Fitted long sleeves
    • Square neckline
    • Form-hugging fit
    • Relaxed midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5933

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Arrival Tie-Front Slit Midi Dress

    Arrive in this charming bodycon midi dress showcasing a flirty bust tie-front and a front slit to give you effortless movement. 

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Sweetheart neckline, tie-front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6032

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Casually Classic Long Sleeve Midi Dress

    The midi-length dress is composed of a cashmere-like soft knit fabrication, features an off-the-shoulder neckline with a popover accent, and long sleeves. Complete look with knee-high boots. 

    Fit & Features

    • Cashmere-like knit fabrication, stretchy knit lining
    • Off-the-shoulder neckline
    • Popover accent
    • Long sleeves
    • Midi length hem
    • Runs true to size 

    Style Number/Barcode: 05102-5960

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch My Glow Mesh Bodycon Mini Dress

    Flirty, fun, and fitted—this abstract mini dress flaunts your gorgeous curves on a sophisticated sleeveless silhouette made for sultry entrances into art galas and cocktail parties.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Mock neck
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000302

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L, XL

  • Pretty Blooms Floral Mesh Halter Maxi Dress

    Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Large floral print pattern
    • Cowl neckline
    • Halter tie-back spaghetti straps, beaded details
    • Open back, lower tie-back spaghetti straps, beaded details
    • Maxi-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5988

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easily Gorgeous Strapless Cable Knit Midi Dress

    Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.

    Fit & Features

    • Cable knit design, soft stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5898

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Charm Halter Pleated Denim Skater Dress

    Showcase a darling charm in this halter denim skater dress with convenient side pockets and a flattering pleated hem!

    Fit & Features

    • Denim fabric
    • Square halter neckline, button closures
    • Side zipper and hook-eye closure
    • Stretchy smocked back
    • Skater silhouette, side pockets
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5954

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free