Casual 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!

  • Preppy Spirit Collared Midi Dress

    Get some pep in your step by styling this casual midi dress for art shows or family dinners! The mid-length dress features a collared V-neckline, long fitted sleeves, and a bodycon silhouette on stretchy ribbed knit fabric. Style with knee-high boots to complete the look!

    Fit & Features

    • Collared V-neckline
    • Long fitted sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4785

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Notice Me Lace Ruffle Mini Dress

    Make 'em' stop and stare at you in this lace mini dress as the chic bride-to-be or gorgeous graduate! The dress features a sleeveless V-neckline, adjustable spaghetti straps that crisscross along the back, a form-hugging fit, and a flirty asymmetrical ruffle trim hem. Complete the look in block heel sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Crisscross back
    • Form-hugging fit
    • Ruffle trim mini-length hem
    • Lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2637

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let It Glitz Glitter Sweetheart Mini Dress

    Let yourself glitz and gleam in this glitter mini dress for party season! It features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps, and a curve-defining asymmetrical mini-length hem with a faux wrap silhouette. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Spaghetti straps
    • Asymmetrical mini-length hem, faux wrap silhouette
    • Bodycon fit
    • Glitter knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4208

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Factor Belted Denim Dress

    From brunch to concert nights, this strapless denim dress delivers instant style. The cinched belt and playful skater skirt keep the vibe equal parts sweet and sassy.

    Fit & Features

    • Denim fabric
    • Strapless neckline
    • Back zipper closure
    • Belted waist
    • Form-hugging bodice
    • Skater mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000207

    Category Name: Casual Dresses

    Price: $62.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Blooming Floral Knit Maxi Dress

    Showcase your beauty as the best-dressed wedding guest in this blooming floral knit maxi dress! Designed with a gorgeous floral print design, it features a sleeveless V-neckline, spaghetti straps that lead to a bold open back with a lace-up strappy design, a thigh-high front slit to show off your heels, and a slim-fit silhouette. Complete your look with sleek hoop earrings.

    Fit & Features

    • Floral printed knit fabric
    • V-neckline, spaghetti straps
    • Open back, cross-back lace-up straps
    • Fitted floor-length skirt
    • High front slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05101-0851

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Flirtation Tie Strap V-Neck Floral Mini Dress

    Imagine how darling and flirty you'll be in this floral mini dress at brunch and parties! The delicate floral print on brushed knit soft fabric adds a playful and romantic touch, perfect for any occasion. Features a plunging neckline and charming tie straps to accentuate your curves while the bodycon fit and mini-length hem add a touch of allure. Complete the look in cute sandals.

    Fit & Features

    • Floral print, brushed knit fabric lined with stretchy knit
    • Tie straps, V-neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5589

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Vacay High Slit Tropical Mesh Midi Dress

    Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.

    Fit & Features

    • Tropical print
    • Stretchy mesh fabric with knit lining
    • Square neckline
    • Spaghetti straps, open cross-back strappy design
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5688

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Ruched Bodycon Mini Dress

    Sleek and smooth, this bodycon mini dress serves curves for days! Crafted from a soft double-lined knit fabric that fits like a glove, this dress features a square neckline adorned with adjustable spaghetti straps, side ruched seams to accentuate your figure along the bodycon silhouette, and a flattering mini-length hem. Complete the look with mules and a crop jacket.

    Fit & Features

    • Soft knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5683

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best Feeling Scoop Neck Cutout A-Line Midi Dress

    There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.

    Fit & Features

    • Modal blend woven fabric with lining
    • Adjustable spaghetti straps
    • Scoop neckline
    • Stretchy smocked bodice with cutout
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5718

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer brunch vibe sweet and stylish in this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a flirty ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with espadrille wedges and a mini handbag.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5800

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Date Night Allure Side Slit Midi Dress

    Give off an enticing allure on your next date night in this sleek knit midi dress! It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Complete the look with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Asymmetric midi-length hem, high side slit
    • Curve-hugging fit
    • Knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5057

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artistic Sensation Strapless Abstract Bubble Mini Dress

    Anytime you step out in this artsy abstract strapless mini dress you'll attract all the attention! The strapless neckline highlights your curves, while the A-line silhouette flatters your figure. The fun and flirty bubble short-length hem adds a playful touch to any occasion. Complete the look with hoop earrings.

    Fit & Features

    • Abstract print, poplin woven fabric, sewn-in knit lining
    • Strapless neckline, non-slip grip lining
    • A-line silhouette
    • Bubble short-length hem
    • Runs small and short, recommend sizing up if needed

    Style Number/Barcode: 05101-3450

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Elevated Strapless Linen-Blend Dress

    Effortlessly elevated, this breezy linen-blend dress is such a summer staple. It features a strapless straight-across neckline, a secure back zipper closure, a ruched fitted high waist, hidden side pockets, and a flowy A-line mid-length silhouette for that relaxed casual-chic vibe. Style with espadrille sandals.

    Fit & Features

    • Linen-blend fabric
    • Strapless straight neckline
    • Back zipper hook-eye closure
    • Ruched high waist
    • Side pockets
    • A-line fit, mid-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5823

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jetset Babe One Shoulder Tropical Maxi Dress

    Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.

    Fit & Features

    • Tropical palm leaf print, stretchy knit
    • One shoulder neckline
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5702

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stun And Only Mock Neck Floral Mesh Mini Dress

    Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Mock neck
    • Sheer long sleeves with slit flare cuffs
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5698

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sweet Tie-Strap Eyelet Mini Dress

    Keep your summer date outfit sweet with the cutest eyelet mini dress! Designed with a lightweight eyelet knit fabric, this adorable short dress will bring the charm. It features a sleeveless square neckline with ruching at the bust, tie-shoulder straps, and a bodycon silhouette with a mini-length hem to flaunt your figure. Style with sneakers for a casual look or mules for a dressier vibe!

    Fit & Features

    • Sheer eyelet knit fabric with knit lining
    • Moderate stretch
    • Ruched square neckline
    • Tie-shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5452

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped Up Cute Off-The-Shoulder Dress

    Serving soft girl vibes with a flirty edge, this off-the-shoulder sweater dress hugs just right. Perfect for latte runs, weekend plans, or anytime you want cozy and cute in one move.

    Fit & Features

    • Soft cable knit fabric with stretch
    • Off-the-shoulder folded neckline
    • Fitted long sleeves
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000153

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: TAUPE, RAISIN

    Available Size: S, M, L, XS

    Product Badge:
    • New Arrival
  • So Effortless Ribbed Knit Bodycon Midi Dress

    This bodycon midi dress is the perfect blend of effortless and chic! Designed with a stretchy ribbed knit fabric for that comfortable fit, this mid-length dress features a trendy sleeveless square neck and back design with thin tank shoulder straps. The ribbed design on the body-hugging silhouette will flaunt your gorgeous figure. Layer on a faux leather jacket and pair with ankle booties for a night out!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Sleeveless square neck and back
    • Tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5585

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Sweet Look Sleeveless Ruffled Skater Dress

    A sweet skater dress for showers or brunch! With its romantic sweetheart neckline and bust tie, you'll feel so flirty. The adjustable spaghetti straps allow for a perfect fit while the ruffled skater silhouette and short-length hem add a touch of playful charm. The partially smocked back offers added stretch. Complete the look with a heart necklace and sandals.

    Fit & Features

    • Gauze woven fabric with stretchy knit lining
    • Sweetheart neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5499

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daytime Cheer Fit And Flare Ruffle Floral Dress

    Spread daytime cheer in this fit and flare floral dress! Made from soft chiffon fabric, this dress is adorned with a ditsy floral print for a whimsical touch.  This playful dress features a sweetheart neckline with ruffle trim, adjustable spaghetti straps, and a charming keyhole bust tie. The stretchy smocked waist and tiered ruffled hem create a flattering fit and flare silhouette. Complete the look with a cute purse and sandals!

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Ruffle trim sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5447

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Feelings Sleeveless Ditsy Floral Mini Dress

    Give yourself a sweet feeling in this ditsy floral mesh mini dress perfect for spring and summer soirees! With a sweetheart neckline, padded bra cups, and adjustable spaghetti straps you;ll feel confident and comfortable. The side ruched seams accentuate your curves along the bodycon fit for a playful touch. Complete the look with a choker necklace.

    Fit & Features

    • Ditsy floral print, mesh fabric, sewn-in knit lining, stretchy
    • Adjustable spaghetti straps
    • Sweetheart neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5550

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fawn Over You Marble Print Chiffon Skater Dress

    You'll be fawned over when in this marble print chiffon skater dress! From the adjustable spaghetti straps to the flattering square neckline, this dress has got you covered. The stretchy smocked bodice creates a comfortable and perfect fit, while the tie waist belt accentuates your curves. With a playful ruffled tiered short-length hem, this dress is perfect for twirling! Complete the look in wedges for a dressy occasion.

    Fit & Features

    • Marble print, chiffon lined fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Tie waist belt, ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3081

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Perfection Bodycon Striped Mini Dress

    With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!

    Fit & Features

    • Striped pattern, texture knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline with twist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5675

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Factor Chiffon Sweetheart Midi Dress

    Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, stretchy smocked back
    • Ruched bust, cutout waist
    • A-line silhouette, front slit
    • Midi-length hem
    • Chiffon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-3189

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale