Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater 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!

  • Lily Girl A-Line Mini Dress

    A girl like you will love this floral mini dress for a sweet summer vibe! It features a sleeveless V-neck, spaghetti straps that lace up on the open-back design, a bodycon A-line silhouette, and a front slit accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Open-back with lace-up design
    • Bodycon A-line silhouette
    • Front slit accent
    • Mini-length hem
    • Floral print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4618

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jetset Getaway Tropical Midi Dress

    Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Open-back, cross-back strap design, tie closure
    • Form-fitting silhouette
    • Side ruched seam
    • Asymmetrical midi-length hem, side slit
    • Tropical floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4373

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Cruise Floral Midi Dress

    You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-back strap design
    • Side ruching
    • Midi-length, form-fitting silhouette, asymmetrical hem
    • Tropical floral print
    • Stretchy knit fabric, partial lining at the bust
    • Runs true to size

    Style Number/Barcode: 05102-4375

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mystic Swirls Square Neck Mini Dress

    Create a sultry-mystic vibe for the night in this square neck dress featuring sleek spaghetti straps and a bodycon silhouette with backside ruching that accentuates every curve on the mesh-lined fabric. Complete the look in lucite mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ruched back detailing
    • Marble swirl pattern
    • Mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4453

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Perfect Gingham Mini Dress

    This gingham plaid mini dress is picnic-perfect! It features a sleeveless, sweetheart neck with adjustable bust tie and keyhole cutout, spaghetti straps, and a bodycon silhouette on stretchy knit-lined fabric. Complete the look in espadrille wedges for a day date.

    Fit & Features

    • Sleeveless, sweetheart neck, spaghetti straps
    • Adjustable bust tie, keyhole cutout
    • Bodycon silhouette
    • Mini-length hem
    • Gingham plaid print
    • Stretchy knit-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4694

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Day Ribbed Short Dress

    Keep it casual in a cute short dress that is ready for brunch with the squad! The dress features a sleeveless V-neckline with ruching at the center, bungee spaghetti straps, and a short-length hem. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless V-neckline 
    • Ruching at center of bodice
    • Bungee spaghetti straps
    • Short length hem 
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06002-1394

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sea Breeze Tropical Midi Dress

    Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruching down one side
    • Midi-length, asymmetrical hem, side slit
    • Curve-hugging silhouette
    • Palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4421

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist of Fate One Shoulder Mini Dress

    Simply stunning and ready for date night or a bridal celebration, this sleek one-shoulder mini dress is made to hug in all the right places to flaunt your sultry curves!

    Fit & Features

    • Smooth woven stretch fabric
    • One-shoulder neckline with twist strap
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000298

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • Pretty As A Rose Crew Mini Dress

    Look and feel pretty as a rose in this ditsy floral mini dress featuring a sleeveless crew neck, a bodycon silhouette, and adjustable ties at the hem that let you customize the length. Complete your look in a dainty bracelet for a backyard bbq.

    Fit & Features

    • Sleeveless, crew neck
    • Ruching down the side seams
    • Adjustable ties at the hem
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4713

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Occasion Ruched Side Mini Dress

    Your next daytime occasion calls for this floral mini dress featuring a sleeveless, square neck, spaghetti straps, and side ruched seams that accentuate your curves on the soft-knit fabric. Complete the look with a cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Soft-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4606

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Florals Short Dress

    Keep it pretty in a short dress that brings the charm! The dress features a pretty daisy print, a halter neck with neck ties, a square-neck smocked bodice, and a triple-row bar strap design at the back. The slim fit bodice leads to a fluttery A-line short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules

    Fit & Features

    • Halter neck with adjustable neck ties
    • Square-neck smocked bodice
    • Triple-row bar strap design 
    • Floral print
    • A-line, short length hem
    • Lined lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4401

    Category Name: Casual Dresses

    Price: $46.90

    Availability: Out of Stock

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

    Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Asymmetrical slit, side ruching
    • Midi-length hem
    • Tropical floral print, texture-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1455

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Treat Puff Sleeve Mini Dress

    This puff sleeve mini dress is the perfect sunny day sweet treat! It features a scoop neck, empire waist seam, bodycon silhouette, and a mini-length hem on jersey knit-lined fabric with a moderate stretch. Complete the look with a chic crossbody bag for a day out.

    Fit & Features

    • Puff sleeves
    • Scoop neck
    • Empire waist seam
    • Bodycon silhouette
    • Mini-length hem
    • Jersey knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4677

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Story Scoop Neck Mini Dress

    It's a love story so baby, just say yes to this floral mini dress! It features a sleeveless, scoop neck, spaghetti straps, a bust tie-front detail, and a bodycon silhouette on rib-knit fabric. Complete the look in cute sandals for a lunch date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bust tie-front detail
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral pattern
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4402

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch Vibes Eyelet Skater Dress

    Sweet and flirty, this eyelet knit skater dress is a must for weekend brunch! It features a sleeveless V-neckline with halter spaghetti straps, an open-back design, and a short skater skirt with a fit and flare silhouette. The lightweight knit fabric features an all-over floral eyelet pattern. Complete your look with a denim jacket and sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie-back closure
    • Open-back design
    • Fit and flare silhouette
    • Skater style-short skirt
    • Floral eyelet knit fabric, lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4420

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daisy Darling Sleeveless Short Dress

    Fall into a daisy daze with a short dress that brings all the feels! The dress features a sleeveless square neckline with lace trim, spaghetti straps, a pretty daisy print, and a short-length hem. The dress is composed of a brushed knit fabric with a form-hugging fit and moderate stretch. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless square neckline, lace trim
    • Spaghetti straps
    • Daisy floral print
    • Short length hem
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4479

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You'll Be Back Twist Bodycon Dress

    You'll be back wearing this sultry bodycon dress on repeat! It features a sleeveless square neckline, sleek spaghetti straps, a mini-length hem, and an open back with dual twist accents that add sultry detail to your look. Style with a necklace and heels for a daytime party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Open-back, dual twist accents
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4592

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shift In Seasons Floral Skater Dress

    The sun rises with the shifting seasons and this flirty floral skater dress is ready to make an appearance! Featuring a sleeveless, square neckline, spaghetti straps, a smocked bodice, and a flowy, short skirt. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, square neckline, spaghetti straps
    • Smocked bodice
    • Skater short silhouette
    • Floral print
    • Swiss dot chiffon, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1507

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Girl Era Strapless Ponte Mini Dress

    This strapless mini dress is giving timeless cute with a flirty edge. Just add hoops and your fave platform shoes.

    Fit & Features

    • Ponte fabric, stretch lining
    • Strapless tube neckline
    • A-Line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000271

    Category Name: Casual Dresses

    Price: $35.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Decision Eyelet Tie-Back Dress

    A sleek and easy piece to dress up or down? Decision made! Keep it trendy in this eyelet lace mini dress designed in a sleeveless scoop neckline, spaghetti straps, tie-back detail, and a bodycon silhouette. Complete the look in basic heels for an outdoor dinner party.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Tie-back detail
    • Eyelet lace-lined fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4422

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Breeze Crochet Maxi Dress

    Look and feel like a daydream in this boho maxi dress designed in a breezy, silhouette featuring a sleeveless, crochet lace v-neck bodice, spaghetti straps, and a sultry open-back with a tie closure that leads to the flowy long hem. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless, crochet lace v-neck bodice, spaghetti straps
    • Open-back, tie closure
    • Flowy maxi silhouette
    • Long-length hem
    • Partially lined woven fabric
    • Fits true to size

    Style Number/Barcode: 05102-4449

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finest Floral Tie-Back Skater Dress

    The florals on this skater dress are oh-so-fine! Create a cute spring look in this sleeveless, boat neckline, adjustable spaghetti straps, a flirty open-back with tie closure, and a ruffled skater silhouette. Complete the look in stud earrings for Easter brunch.

    Fit & Features

    • Sleeveless, boat neckline, adjustable spaghetti straps
    • Open-back, tie closure
    • Ruffled skater silhouette
    • Short hem
    • Floral chiffon-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4432

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Innocent Charm Eyelet V-Neck Dress

    Innocently charming! Bring the flirtiness in this eyelet v-neck dress featuring a sleeveless ruffle trim bodice with tie-front closure, spaghetti straps, a cutout accent, and a form-fitting silhouette. Complete the look in a dainty choker necklace for a day date.

    Fit & Features

    • Sleeveless, v-neck, ruffle trim, spaghetti straps
    • Tie-front closure
    • Cutout accent
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4536

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced Up And Lovely Floral Corset Dress

    Giving a fairytale with a flirty twist. This corset mini dress brings the drama with lace trim, a lace-up back, and a twirl-worthy skater skirt perfect for celebrations or garden soirees!

    Fit & Features

    • Floral print, woven fabric, woven lace trim lining
    • Sweetheart lace trim neckline, bust tie, underwire bust
    • Lace trim, adjustable shoulder straps
    • Corset lace and pleated trim bodice, flexible boning
    • Back zipper and hook-eye closure, lace-up back detail
    • Drop waist seam, voluminous skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000067

    Category Name: Casual Dresses

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free