Casual Dresses

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Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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!

  • Dreamy Vacay Vibes Midi Dress

    Get those dreamy vacay vibes in this stunning midi dress! It features a sleeveless V neckline, adjustable spaghetti straps, an asymmetric mid-length hem with a side slit, and a curve-hugging silhouette. The knit fabric has a gorgeous all-over tropical floral print. Complete the look with strappy sandals and some cute sunnies.

    Fit & Features

    • V neckline
    • Adjustable spaghetti straps
    • Asymmetric mid-length hem
    • Side slit
    • Form-hugging fit
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-0586

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Vibes Tie-Dye Knit Mini Dress

    Bring the casual vibes this season with this trendy tie-dye knit mini dress. It features a crew neckline, short sleeves, side ruching, and a mini-length, curve-hugging silhouette with side ties at the hem. Complete the look with cute sneakers for the perf everyday outfit.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Side ruching
    • Side ties at the hem
    • Short, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1588

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Stunner Crepe Mini Dress

    Create a casual stunning look with this adorable crepe mini dress that is perf for every day. It features a sleeveless bodice, spaghetti straps, a square neckline, a cute tie-back detail, and a mini-length, curve-hugging silhouette. Style the dress with the tie in the front for a night out. Complete the outfit with a layered necklace and new mules.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Tie-back detail
    • Short, form-hugging fit
    • Crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-0527

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Ditsy Floral Smocked Mini Dress

    Level up the charm with this adorable ditsy floral printed mini dress! It features tie shoulder spaghetti straps, a square neckline with a ruffle trim, a tie-front at the bust, a high waist seam, and a smocked body with a mini-length, curve-hugging silhouette. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Square neckline, ruffle trim
    • Tie-front at the bust
    • High waist seam
    • Smocked body
    • Short, form-hugging fit
    • Woven fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1109

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Style Floral Mini Dress

    Showcase the sweetest style this summer season in this floral mini dress! It features a sleeveless bodice, spaghetti straps, a sweetheart neckline with a tie-front at the bust, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over adorable ditsy floral print that will pair perfectly with a denim jacket and sandals.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Knit fabric, moderate stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1431

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab And Retro Tie-Dye High Slit Maxi Dress

    Keep it fab with a dress that channels a retro feel! The maxi dress features a sleeveless scoop neckline, spaghetti straps, a tie-dye print, a high side slit, and a maxi length silhouette. The dress is composed of a ribbed kit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti strap
    • Tie-dye print
    • High side slit
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1122

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Chic Ruffled A-Line Mini Dress

    Channel your bohemian side with a pretty mini dress that channels those lowkey vibes. The dress features a sleeveless square neckline, tie-up shoulder straps, tiered ruffles, and a mini-length A-line silhouette. Complete look with cork wedges

    Fit & Features

    • Sleeveless square neck 
    • Tie-up shoulder straps
    • Tiered ruffles
    • Mini length 
    • A-line silhouette
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1046

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shrug It Off One-Shoulder Bodycon Mini Dress

    This is the perfect sleeveless mini dress for parties and cocktail hour! It features a sassy one-shoulder neckline and a sexy bodycon silhouette. Pair with boots.

    Fit & Features

    • Rib knit fabric, stretchy knit lining
    • One-shoulder neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5900

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Drawn To You Ruched Mini Dress

    Get drawn into this fab mini dress that is perf for your next date night with bae! The dress features a sleeveless sweetheart neckline, a small keyhole with a ruched drawstring, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline
    • Keyhole
    • Ruched drawstring
    • Mini length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0664

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Stunner Ruched Mini Dress

    Bring stylish and stunning looks this season in this on-trend mini dress. It features a crew neckline, short sleeves, a front waist cutout with a cross-strap design, ruching, and a mini-length silhouette with ties at the hem. Pair this dress with heeled mules and a chic crossbody purse.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Front waist cutout, cross-strap design
    • Ruching
    • Short, form-hugging fit
    • Ties at the hem
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-2029

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Babe Denim Bodycon Mini Dress

    You'll be such a babe in this denim bodycon mini dress that is a summer must-have! It features short puff sleeves, a square neckline with a corset-designed bodice, a back zipper closure, and a mini-length, curve-hugging silhouette. Complete the look with heeled mules and a pair of chic sunglasses.

    Fit & Features

    • Short puff sleeves
    • Square neckline
    • Corset-designed bodice
    • Back zipper closure
    • Short, form-hugging fit
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-2356

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibes Off The Shoulder Floral Mini Dress

    Channel those flirty vibes with a pretty mini dress! The vibrant dress features an off-the-shoulder neckline with short puff sleeves, a mini tie-front, a ditsy floral print, a smocked back, and a mini-length silhouette. The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Off the shoulder neckline, short puff sleeves
    • Mini tie-front smocked back
    • Ditsy floral print
    • Mini length silhouette 
    • Crinkle-crepe fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0573

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirtatious Vibes Floral Mini Dress

    Bring the flirty vibes in this adorable floral mini dress perf for summer! It features an off-the-shoulder sweetheart neckline with a ruffle trim, a tie-front detail, short puff sleeves, an all-over ditsy floral print, and a mini-length, curve-hugging silhouette. Complete the look with cute wedges for a weekend brunch.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, ruffle trim
    • Tie-front detail
    • Short puff sleeves
    • Ditsy floral print
    • Brushed knit fabric, moderate stretch
    • Short, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Bloom Mesh Mini Dress

    Soft meets fierce in this mesh dress—floral, animal print, and all eyes on you. The open back and flared sleeves bring that extra touch for plans that need a little drama.

    Fit & Features

    • Floral, leopard print, mesh fabric, stretchy knit lining
    • Boat neckline
    • Long flared sleeves
    • Open back with adjustable tie closure
    • Form-hugging silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000217

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Glam Tie Dye Ruched Mini Dress

    Keep it so glam with a tie-dye dress that gives your look a retro feel! The dress features a sleeveless square neckline, bungee spaghetti straps, a tie-dye print, a ruched side seam, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in new top-rated shoes

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Tie-dye print
    • Ruched side seam
    • Mini length silhouette 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1083

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Sleeveless Colorblock Mini Dress

    Channel a retro moment with a mini dress that makes a stylish statement. The dress features a sleeveless crew neckline, a colorblock design accented with exposed seams, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless crew neckline
    • Colorblock pattern with exposed seams
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2064

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Cutie Ruched Mini Dress

    Create a chic look with a mini dress that showcases your stunning style! The mini dress features a sleeveless crew neckline, a waist cutout that creates an O-ring design, a ruched drawstring, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. 

    Fit & Features

    • Sleeveless crew neckline
    • Waist cutout 
    • Ruched drawstring 
    • Mini length silhouette 
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1968

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Charm Ruched Mini Dress

    Bring the charm with a butterfly print dress that springs you into the season. The mini dress features a sleeveless square neckline, spaghetti straps, a butterfly print, a ruched body, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with butterfly earrings and wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Butterfly print
    • Ruched body
    • Mini-length silhouette, form-hugging fit
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1454

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Dreamy Ditsy Floral Mini Dress

    Keep it dreamy with a floral mini dress that brings the romance. The dress features a sleeveless V-neckline with a ruched center, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline with ruched center
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette 
    • Lined ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2047

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summertime Stunner Mini Dress

    Show off your stunning style this summer in this gorg mini dress! It features a sleeveless sweetheart neckline with a ruffled trim, spaghetti straps, center ruching with a drawstring at the hem, and a mini-length, curve-hugging silhouette. Complete the outfit with cute wedges for the perfect graduation look.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Ruffled trim
    • Spaghetti straps
    • Center ruching, drawstring at hem
    • Short, form-hugging fit
    • Eyelet knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1205

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Stunning Floral Chiffon Skater Dress

    Style up this adorable floral chiffon dress for a simply stunning look. It features a sleeveless V neckline, adjustable spaghetti straps, front buttons, a fitted bodice, and a flirty skater skirt silhouette. Complete the outfit with hoop earrings and a straw tote.

    Fit & Features

    • Sleeveless V neckline
    • Adjustable spaghetti straps
    • Front buttons
    • Fitted bodice, smocked back
    • Back zipper closure
    • Skater skirt silhouette
    • Floral chiffon fabric
    • Runs true to size

    Style Number/Barcode: 05102-0545

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Style Tie-Front Maxi Dress

    Showcase a chic effortless style this season with this adorable maxi dress! It features a sleeveless V neckline, adjustable spaghetti straps, a tie-front detail with a small cutout, center button accents, and a flowy fit with a center slit. Pair this ribbed knit dress with a straw tote and strappy sandals.

    Fit & Features

    • Sleeveless V neckline
    • Adjustable spaghetti straps
    • Tie-front, small cutout
    • Fitted bodice
    • Center button details
    • Flowy silhouette, center slit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1174

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Impressions Sleeveless Midi Cutout Dress

    Make a bold impression with a midi dress that cuts a sultry look! The midi dress features a plunging V-neckline, spaghetti straps, sexy cutouts at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual cutouts at the waist
    • Midi-length silhouette
    • Sheer ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1967

    Category Name: Casual Dresses

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Darling Strapless Bodycon Mini Dress

    A denim bodycon mini dress for a darling look paired with your fave boots at concerts and festivals!

    Fit & Features

    • Denim fabric, sewn-in knit lining, minimal stretch
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5901

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free