Casual Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

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!

  • Cool Girl Chic Strapless Abstract Mesh Mini Dress

    Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!

    Fit & Features

    • Stretchy sheer mesh fabric with soft knit lining
    • Abstract print
    • Strapless straight elasticized neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5558

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Cutie Bow Lace-Up Floral Mini Dress

    Look effortlessly cute in this floral mini dress this summer! The stretchy knit fabric is accented with a dainty floral print for a charming look. This bodycon dress features adjustable spaghetti straps and a sleeveless square neckline adorned with a ribbon bow and delicate crochet trim for a touch of elegance. The lace-up back allows for a perfect fit while the mini-length hem adds a flirty touch. Style with statement earrings.

    Fit & Features

    • Floral print, stretchy knit fabric
    • Square neckline with ribbon bow and crochet trim
    • Adjustable spaghetti straps
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5665

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Chic Floral Chiffon Midi Dress

    Enchanting and chic, this floral chiffon midi dress is perfect for a garden wedding. It features a sleeveless sweetheart neckline with a bust outline, adjustable spaghetti straps, a high waist seam, a smocked back panel with a zipper closure, a midi-length hem with a high front slit, and a flowy A-line silhouette. The airy chiffon fabric features a romantic blooming floral print alongside a dainty flower pattern. Style with clear block heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust and outline
    • Adjustable spaghetti straps
    • High waist seam, stretchy smocked back, zipper and hook-eye closure
    • Midi-length hem
    • Front slit, A-line silhouette
    • Floral print, chiffon fabric, smooth stretchy knit lining
    • Style runs small

    Style Number/Barcode: 05101-2212

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Going Places Strapless A-Line Pleat Denim Mini Dress

    Look cute in this denim mini dress for all of the places you're going to! This dress features a strapless neckline with a non-slip grip lining for a secure fit. The fitted A-line silhouette flatters your figure, while the belted waist adds a trendy look to the pleated mini-length hem. Complete the look with hoop earrings and sandals!

    Fit & Features

    • Denim fabric with stretch
    • Non-slip grip lining, back zipper closure
    • Belted waist
    • Fitted A-line silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5471

    Category Name: Casual Dresses

    Price: $52.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can't Deny Strapless Cargo Mini Dress

    Cargo will forever be a classic and this strapless mini dress is no exception! It features trendy contrast stitched seams, a flattering bodycon silhouette, side cargo-style flap pockets, and a mini-length hem on textured knit fabric. Style with a cute crop jacket for a casual dinner and movie!

    Fit & Features

    • Strapless neckline
    • Back zipper and hook-eye closure
    • Contrast stitched seams
    • Bodycon silhouette
    • Side cargo-style flap pockets
    • Textured knit fabric, moderate stretch
    • Mini-length hem

    Style Number/Barcode: 05102-5377

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow Your Heart Sleeveless Ruffled Lace Maxi Dress

    Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3382

    Category Name: Casual Dresses

    Price: $28.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make An Impression Cowl Neck Bodycon Mini Dress

    Make an impression in this abstract print mesh mini dress for an artsy vibe!  With a halter cowl neckline and a spaghetti strap tie, you'll turn heads wherever you go. Side ruched seams create a flattering, bodycon fit that accentuates your curves along the mini-length hem. Complete the look in hoop earrings and a clutch!

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Halter cowl neckline, spaghetti strap tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5785

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Cute Ruffled Drop Waist Skater Dress

    Keep it cute every time in this strapless skater dress designed with a flirty ruffled short-length hem. Pair it with sleek heels.

    Fit & Features

    • Ponte knit fabric with partial knit lining, moderate stretch
    • Strapless straight neckline, fold-over design
    • Drop waist
    • Mini-length tiered ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3756

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leaving Impressions Strapless Ribbed Knit Midi Dress

    You'll be leaving chic impressions in this ribbed knit midi dress! It features a strapless neckline, a flirty cutout waist with contrast trim, a flattering bodycon silhouette, and a side slit accent on stretchy rib knit fabric. Complete the look in this mid-length dress with simple hoop earrings for a birthday dinner!

    Fit & Features

    • Strapless neckline
    • Cutout waist, contrast trim
    • Bodycon silhouette, side slit accent
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-2042

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cascading Romance Ruffle Floral Skater Dress

    Get swept away into a world of romance in this floral skater dress perfect for a shower or date! The square neckline and tie-shoulder spaghetti straps add a touch of sweetness, while the stretchy smocked bodice ensures a comfortable fit. The skater silhouette and tiered ruffled hem make this dress perfect for twirling the night away. Complete the look with earrings.

    Fit & Features

    • Floral print, chiffon fabric with woven skirt lining
    • Square neckline
    • Tie-shoulder spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette with ruffles
    • Runs true to size

    Style Number/Barcode: 05101-2994

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Effect Ruffled Denim Skater Dress

    You'll always make a trendsetting impression in this denim skater dress perfect for country concerts or the fair. Featuring a square neckline, wide shoulder straps, and faux button closures, this dress flatters your figure with its underbust seam and skater silhouette. The ruffled hem adds a fun touch to the stylish denim twill fabric. Complete the look in cute cowboy boots.

    Fit & Features

    • Denim twill fabric with minimal stretch
    • Square neckline
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5472

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Untamed Denim Strapless Mini Dress

    Bold, fitted, and a stunner. This strapless lace-up denim mini dress is the perfect piece for when you want to keep it casual but still turn heads.

    Fit & Features

    • Denim fabric
    • Strapless neckline
    • Back zipper closure
    • Front lace-up placket
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000272

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

    Product Badge:
    • Halloween Badge
  • Cute Perfection Scoop Neck Bow Skater Dress

    You'll look like cute perfection in this sleeveless skater dress at soirees! With adjustable spaghetti straps, a flattering scoop neckline, and three adorable bows with ruffle trim, this skater dress will have you feeling confident and stylish in its short-length hem. Complete the look in trendy sandals and a hair accessory.

    Fit & Features

    • Airy chiffon fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Scoop neckline
    • Back zipper and hook-eye closure 
    • Three bows with ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3453

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Energy Ruffle Skater Dress

    Playful yet sultry, this ruffle skater dress brings flirty energy with every move. The strappy open back and layered ruffled hem make it the perfect go-to for nights out or weekend plans.

    Fit & Features

    • Knit fabric
    • Sleeveless plunging V-neckline, bar strap detail
    • Tie-back halter spaghetti straps
    • Open back, lower tie-back spaghetti straps
    • Drop waist, tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000284

    Category Name: Casual Dresses

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Chic Smooth Knit Fitted Maxi Dress

    This smooth knit fitted maxi dress is the casually chic style you need to elevate your 'fits. It features a strapless straight-across neckline, an all-over curve-hugging silhouette, a maxi-length hem, and a trendy back slit accent. The smooth knit fabric includes an airy sheer mesh lining and offers plenty of stretch for comfortable wear. Complete your looks with strappy mules and a mini handbag.

    Fit & Features

    • Strapless straight-across neckline
    • Curve-hugging silhouette
    • Maxi-length hem
    • Back slit
    • Smooth knit fabric, sheer mesh lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5175

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Unique Feels Abstract Print Mock Neck Maxi Dress

    Showcase your unique style in this artsy abstract print maxi dress for a gallery opening or a wine bar! It features cap sleeves, a mock neck, and a bodycon silhouette. The dress is composed of a sheer mesh fabric with a stretchy knit maxi slip lining with adjustable spaghetti straps, a scoop neck, and a fitted hem. Complete the look in platform sandals.

    Fit & Features

    • Cap sleeves
    • Mock neck
    • Bodycon silhouette, maxi-length hem
    • Abstract print, mesh fabric
    • Stretchy knit maxi slip lining, adjustable spaghetti straps
    • Scoop neck, fitted hem
    • Runs true to size

    Style Number/Barcode: 05102-5208

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Casual Cool Girl High Slit Ribbed Knit Maxi Dress

    Showcase a casual cool girl style in this curve-hugging maxi dress. Designed with a stretchy ribbed knit fabric, it features a sleeveless crew neckline, tank shoulder straps, a trendy side cutout at the waist to showcase some skin, and an alluring thigh-high side slit on the maxi-length hem. Complete your look with clear mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Crew neckline
    • Tank shoulder straps
    • Side cutout at the waist
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05102-4906

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Town Strapless Floral Crepe Mini Dress

    The perfect floral crepe mini dress to take with you out of town! Boasting a strapless neckline, this mini-length dress has a trendy contrast foldover design and a bodycon silhouette that flatters your curves. Complete the look in sandals and sunnies!

    Fit & Features

    • Floral print, crepe fabric lined with stretchy knit
    • Contrast foldover design
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3364

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Attention Collared Cargo Mini Dress

    Capture all the attention in this structured and chic cargo mini dress! It features a sleeveless collared neckline, a complete zip-front design creating a V-neckline, a faux belted waist, large cargo-style side pockets, a mini-length hem, and a streamlined form-hugging fit. The woven fabric offers minimal stretch. Style this mini dress with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless collared neckline
    • Complete zip-front, V-neckline
    • Faux belted waist, large cargo side pockets
    • Mini-length hem
    • Form-hugging fit
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5103

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stroll The Beach V-Neck Floral Paisley Maxi Dress

    Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!

    Fit & Features

    • Floral paisley print, woven fabric, stretchy knit lining
    • Adjustable spaghetti straps, crisscross back
    • Stretchy smocked V-neckline
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5566

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Sweetheart Halter Marble Print Midi Dress

    Look naturally cute for any occasion in this marble print midi dress! The cowl halter neckline and flowy silhouette add a relaxed style, while the side slit and midi-length hem add flirty touches. Complete the look in strappy sandals and a clutch!

    Fit & Features

    • Marble print, mesh fabric lined with stretchy knit
    • Cowl halter neckline with tie closure
    • Flowy silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5593

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Eyelet Lace Skater Dress

    You'll look sweet as can be in this eyelet lace skater dress perfect for swaying with the music at day parties! Designed with a sheer eyelet lace fabric and knit lining, it features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, a flirty tie-back design, and a flattering fit and flare silhouette with a short hem. Complete the look in lace-up heels.

    Fit & Features

    • Sheer eyelet lace fabric, knit lining, minimal stretch
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Tie-back design
    • High waist seam
    • Fit and flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5466

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Dreams Halter V-Neck Boho Chiffon Maxi Dress

    Summer dreams are made of this boho chiffon maxi dress perfect for your vacation or weekend getaway! The halter V-neckline and spaghetti strap tassel ties provide an effortlessly chic touch, while the stretchy smocked bodice and hidden side pockets offer convenience. The flowy ruffled silhouette adds a touch of romance! Complete the look in sandals and a bracelet.

    Fit & Features

    • Bohemian print, chiffon fabric with woven lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Hidden side pockets
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5777

    Category Name: Casual Dresses

    Price: $6.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale