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!

  • Mesh Well Square Neck Mini Dress

    You and this mini dress will mesh well together! It features adorable sheer puff short sleeves with ruffle trim, a square neckline, a ruched bust and side seams, and a flattering bodycon silhouette. Complete the look with a statement choker for a family party!

    Fit & Features

    • Sheer puff short sleeves, ruffle trim
    • Square neckline
    • Ruched bust and side seams
    • Bodycon silhouette
    • Mini-length hem
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5098

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Weekend Vibes One-Shoulder Midi Dress

    This sultry curve-hugging midi dress gives off major summer weekend vibes! It features an asymmetric one-shoulder neckline with dual adjustable spaghetti straps, an alluring open back with an asymmetric strap design, a midi-length hem, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with platform wedges for dinner and drinks.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Dual adjustable spaghetti straps
    • Open back, asymmetric strap design
    • Midi-length hem
    • Bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5173

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacation Mode Tropical Print Maxi Dress

    Activate vacation mode with this sultry tropical print maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, ruching down the side seam leading to an alluring thigh-high slit, an asymmetric maxi-length hem, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features an all-over bold tropical palm leaf pattern. Style with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • Ruched side seam, high side slit
    • Asymmetric maxi-length hem, bodycon silhouette
    • Tropical palm leaf print
    • Smooth knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5055

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Showcase Your Charm Sheer Lace Maxi Dress

    Showcase your charm in this airy sheer lace flowy maxi dress. It features a V-neck and back with wrap designs, tie-back straps, short billowy bell sleeves with slit accents, a stretchy smocked high waist, a partial button-down design leading to a high front slit, a maxi-length silhouette with an adorable ruffled hem, and an A-line fit. The dainty sheer lace fabric includes a partial mini-length woven lining. Complete your look with espadrille wedges for a summer party.

    Fit & Features

    • V-neck and back, wrap designs, tie-back straps
    • Short bell sleeves, slit accents
    • Stretchy smocked high waist
    • Partial button-down design, high front slit
    • Maxi-length silhouette, ruffed hem, A-line fit
    • Sheer lace fabric, partial mini-length woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5003

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Somewhere Tropical V-Neck Midi Dress

    You deserve to go somewhere tropical with this midi dress as your inspiration! It features a sleeveless V-neckline, spaghetti straps, a curve-hugging silhouette, and a flirty slit hem. The dress is composed of a palm-printed stretchy knit fabric. Complete the look in strappy-heeled sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Curve-hugging silhouette
    • Slit midi-length hem
    • Palm print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4966

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Sun Rib Knit Mini Dress

    Ready for some sun? Let this rib knit mini dress cue the sunshine! It features a sleeveless scoop neckline, a flirty bust tie with a keyhole accent, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a backyard bbq!

    Fit & Features

    • Sleeveless scoop neckline
    • Bust tie, keyhole accent
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5149

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office Tropical Print Maxi Dress

    Packing this gorgeous tropical print maxi dress in your carry-on is a must for your vacay getaway! It features a sleeveless V-neckline with an O-ring accent at the bust, a sultry waist cutout at the front, adjustable spaghetti straps, a fitted, flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with cute wedges.

    Fit & Features

    • Sleeveless V-neckline, center O-ring bust accent
    • Front waist cutout
    • Adjustable spaghetti straps
    • Fitted, flowy, floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, short-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5015

    Category Name: Casual Dresses

    Price: $9.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely Day Tie Back Ruffle Skater Dress

    Perfect for any occasion, this skater dress will make you stand out in style! The tie back adds a touch of charm while the ruffled details bring a playful and flirty vibe to the mini-length hem.

    Fit & Features

    • Woven fabric, woven lining
    • Square neckline, spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000025

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: NAVY

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

  • Chic To Be Lace Crepe Mini Dress

    They can also pronounce you chic to be with this gorgeous crepe mini dress on! Perfect for bridal showers, rehearsal dinners, and other celebrations. Featuring a sleeveless sweetheart neck, wide straps, a lovely lace-lined bust with underwire and a bow, a pleated side seam, and a crepe bodycon skirt. Complete the look in rhinestone mules.

    Fit & Features

    • Sleeveless sweetheart neck
    • Wide straps, back zipper and hook-eye closures
    • Lace-lined bust, underwire, bow
    • Pleated side seam
    • Crepe bodycon skirt
    • Lined, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2122

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Thing Off-The-Shoulder Mini Dress

    Show your sweet side in this must-have mini dress for a stylish look at every event! It features an off-the-shoulder neckline, short sleeve cuffs, all-over ruching with an adjustable front drawstring, and a bodycon silhouette. The lined mesh fabric offers plenty of stretch. Complete the look in platform sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer short sleeve cuffs
    • All-over ruching, adjustable front drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Sheer mesh fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2399

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Perfection Cutout Midi Dress

    This chic cutout midi dress is elevated perfection! It features a sleeveless subtle sweetheart neckline with a knot detail at the center of the bust, an alluring keyhole cutout under the bust, spaghetti straps, a high waist seam to create a figure-flattering look, a midi-length hem with a thigh-high side slit, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Style with a pair of strappy stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline, center knot detail
    • Keyhole cutout under the bust
    • Spaghetti straps
    • High waist seam, midi-length hem, high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5121

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Double Take Strappy Back Mini Dress

    This casual mini-dress will make everyone do a double-take! It features a sleeveless scoop neckline, spaghetti straps, an open back with a caged strap design, a bodycon silhouette, and a mini-length hem. The dress is composed of a stretchy rib knit fabric with a sewn-in knit lining. Complete the look in hoop earrings for a backyard bbq.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open back, caged strap design
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5156

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call You Sweetheart Ruffle A-Line Dress

    Everyone will be calling you sweet in this short A-line dress as the bride-to-be or graduate! It features a sleeveless sweetheart neck, tank shoulder straps, a ruched bust seam, a flattering A-line silhouette, asymmetrical front ruffle trim, and a short-length hem. Complete the look with earrings and block heels.

    Fit & Features

    • Sleeveless sweetheart neck
    • Tank shoulder straps
    • Ruched bust seam
    • A-line silhouette, asymmetrical ruffle trim
    • Short-length hem
    • Slinky knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05101-2480

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strolling The Garden Floral Chiffon Midi Dress

    Stroll the garden looking effortlessly enchanting in this floral chiffon midi dress! It features a sleeveless sweetheart neckline with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a hem slit. Complete the look in strappy sandals for an outdoor wedding.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Bust tie, adjustable spaghetti straps
    • Stretchy smocked back
    • Slit accent, midi-length hem
    • Ditsy floral print, airy chiffon, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2312

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paradise Lost Halter Cutout Midi Dress

    Escape to paradise in this halter midi dress that'll make everyone lose their train of thought! It features a sleeveless halter neckline with tie-back straps, a center O-ring insert and cutout bodice, and a flattering bodycon silhouette with a side slit hem. The brushed knit fabric offers plenty of stretch. Complete the look in bold hoop earrings.

    Fit & Features

    • Sleeveless halter neckline, tie-back straps
    • Center O-ring insert, cutout bodice
    • Bodycon silhouette
    • Side slit, midi-length hem 
    • Partially lined brushed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5068

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Dream Ditsy Floral Mini Dress

    Create a dreamy summer vibe in this adorable floral mini dress perf for sunny weekends! It features a sleeveless V-neckline with ruching at the center of the bust, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, ruching at the bust
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5122

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trip To Paradise Tropical Print Maxi Dress

    This bold and alluring tropical print maxi dress calls for a trip to paradise! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a floor-length hem with a thigh-high front slit, and a flowy silhouette. The smooth knit fabric showcases a tropical palm leaf print. Style with strappy sandals for sunset drinks.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length hem, high front slit, flowy silhouette
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5025

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild And Chic Zebra Print Mini Sweater Dress

    Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.

    Fit & Features

    • Sleeveless V-neckline
    • Halter straps, tie-back design
    • Open back
    • Mini-length hem
    • Curve-hugging silhouette
    • Zebra print, sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1699

    Category Name: Casual Dresses

    Price: $3.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • La Quinta Ditsy Floral Rib Knit Mini Dress

    Let your love for floral bloom in this rib knit mini dress perfect for a visit to the flower fields!  It features a ruffle trim sweetheart neckline and puff short sleeves, a flirty bust lace-up, a bodycon silhouette, and a mini-length hem. Complete the look in cute flat sandals and earrings.

    Fit & Features

    • Ruffle trim sweetheart neckline
    • Ruffle trim puff short sleeves
    • Bust lace-up
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print, stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5171

    Category Name: Casual Dresses

    Price: $5.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Impressions Ruched Mini Dress

    Make a bold impression out and about in this mesh mini dress perfect for parties or sexy brides! It features a sleeveless square neck, bungee spaghetti straps, side ruched seams that accentuate your curves, and a bodycon fit. Complete the look with heart-shaped earrings.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Mesh fabric, nude stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5160

    Category Name: Casual Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Girl Plaid V-Neck Mini Dress

    This plaid mini dress is for all the preppy girls! It features a sleeveless V-neckline, spaghetti straps, a bodycon fit, and a flirty front slit accent on stretchy knit fabric. Style with a cropped blazer and booties to complete the look!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Bodycon fit
    • Front slit accent
    • Mini-length hem
    • Plaid print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5161

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Butterfly Crochet Knit Mini Dress

    Style up this adorable crochet knit mini dress for a casual party vibe! It features a sleeveless V-neckline with the cutest butterfly crochet embroidered design, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The smooth knit fabric includes a full-length lining and offers plenty of stretch. Complete the look with hoop earrings and espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Butterfly crochet embroidered design
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Knit fabric, full-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5065

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Untamed Allure Animal Print Cutout Maxi Dress

    For the nights you want all eyes on you. This sultry animal print cutout maxi dress hugs every curve and serves bold, untamed allure to keep you as the main focus.

    Fit & Features

    • Sheer mesh fabric with mini-length brushed knit lining, high stretch
    • Animal print
    • Sleeveless plunging halter neckline
    • Open back and sides, beaded accents, tie-back straps
    • Maxi-length hem, high-cut side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000278

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Follow The Sun Sweetheart Mini Dress

    Dare to bare some skin on a sunny day in this flirty casual mini dress for hanging by the beach or downtown! It features a sleeveless sweetheart neckline, spaghetti straps, a bust tie with a keyhole accent, and flattering side ruched seams that accentuate your curves along the bodycon fit. Complete the look with cute sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Bust tie, keyhole accent
    • Side ruched seams, bodycon fit
    • Mini-length hem
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5127

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale