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!

  • One Of A Kind A-Line Mini Dress

    Stun in this one-of-a-kind dress that is pef for any occasion! The dress features a square neckline, short puff sleeves, and an A-line silhouette. The dress is composed of a lined textured woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • A-line silhouette
    • Mini length 
    • Textured lined woven fabric
    • Relaxed fit, runs true to size

    Style Number/Barcode: 05102-4239

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Must-Have Midi Sweater Dress

    This basic midi sweater dress is a must-have in your wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, a mid-length, curve-hugging silhouette, and a ribbed sweater knit fabric that offers a moderate stretch. Style this dress with chic mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mid-length, form-hugging fit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0958

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Adored Cut Out Mini Dress

    Feel so beloved in this pretty mini dress! The dress features a scoop neckline, short sleeves, a midriff cutoff with tie waist accent, 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 look with platform heels

    Fit & Features

    • Scoop neckline
    • Short sleeves
    • Midriff cutout, tie waist accent 
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1859

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this fab mini dress! The dress features a square neckline, short puff sleeves, ruching at the bodice, eyelet pattern, and a curve-hugging mini-length silhouette. The dress is composed of a lined woven fabric that offers minimal stretch. Complete look with clear mules

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Ruching 
    • Eyelet pattern 
    • Mini length silhouette 
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1291

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Girl Summer Crochet Maxi Dress

    Keep it stylish with a crochet maxi dress that is perf for your summer adventures! The dress features a sleeveless V-neckline, a crochet waist, an open back with a crochet lace trim, and a maxi-length silhouette. The dress is composed of a woven fabric that offers a relaxed and flowy fit. Complete look with wedges and butterfly hoops.

    Fit & Features

    • Sleeveless V-neckline
    • Crochet waist
    • Open back, crochet lace trim, tie-back closure
    • Lower back hidden zipper and hook and eye closure
    • Maxi-length silhouette, relaxed fit
    • Lightweight woven fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-1330

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Lace-Up Denim Mini Dress

    Keep it basic with a cute denim mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and door knocker earrings. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up back 
    • Mini length silhouette
    • Denim fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0765

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Eyelet Skater Dress

    Create a fashionable moment with a skater dress that is all the rage! The dress features an off-the-shoulder neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. Complete look with wedges

    Fit & Features

    • Off the shoulder neckline
    • Short puff sleeves
    • Eyelet pattern 
    • Skater silhouette
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-1051

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making Moves Sleeveless Mini Dress

    Make stylish moves in this LBD that stuns! The dress features a halter neck with a halter neck strap, a partially open back, and a mini-length silhouette. Complete look with rhinestone heels and a rhinestone bracelet.

    Fit & Features

    • Halter neckline
    • Halter neck strap
    • Triangle-shaped bodice
    • Partially open back 
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0962

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropics Babe High Slit Midi Dress

    Hit the tropics in this gorge midi dress! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, a ruched side seam, and a midi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a floppy hat and sandals

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross at the back 
    • Tropical print 
    • Ruched side seam 
    • Midi length silhouette, high side slit
    • Smooth knit fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1799

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Charm Halter Babydoll Mini Dress

    A charming halter dress for dinner dates or beachside strolls. Its lightweight babydoll silhouette offers a comfortable, flowy fit, while the playful ruffle mini hem brings a flirty finish!

    Fit & Features

    • Woven gauze fabric, woven lining
    • Sweetheart halter neckline, hoop insert, spaghetti strap tie
    • Cutout keyhole accent
    • Padded bra cups
    • Flowy babydoll silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6087

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Thinking Of You Denim Mini Dress

    Leave them thinking of you in this pretty midi dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a button-down front, a cinching tie waist belt, hidden side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a relaxed fit. Complete look with sandals and a cropped denim jacket

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Button-down front 
    • Cinching tie waist belt 
    • Hidden side pockets
    • Mini length silhouette
    • Denim fabric, form-hugging fit, runs true to size

    Style Number/Barcode: 05102-0475

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rainbow Tie Dye Mesh Mini Dress

    Brighten your look with a rainbow mini dress that commands attention! The dress features a sleeveless square neckline, bungee spaghetti straps, a rainbow tie-dye hue, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Rainbow tie-dye
    • Mini length silhouette
    • Mesh fabric 
    • Form hugging fit, runs true to size 

    Style Number/Barcode: 05102-1175

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Groovy Tie-Dye Maxi Dress

    Keep your summer look groovy and on-trend with this tie-dye maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a high waist seam, and a floor-length silhouette with a thigh-high side slit. Style this dress with strappy sandals for a laid-back vibe.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length silhouette, high side slit
    • Relaxed fit
    • Brushed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0745

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Cutout Gauze Knit Skater Dress

    Keep it trendy with a skater dress that keeps it glam for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Waist cutouts with bar straps
    • Skater silhouette
    • Gauze knit fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-0246

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutout Cutie Gauze Skater Dress

    Keep it cute with a skater dress that brings the style! The dress features a sleeveless V-neckline, waist cutouts with bar straps, a striped pattern, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Waist cutouts
    • Bar straps 
    • Striped pattern 
    • Skater silhouette 
    • Gauze knit 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1084

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Style Cutout Maxi Dress

    Showcase a stunning style this season in this trendy maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to the back, and a floor-length, curve-hugging silhouette. Pair this sultry dress with hoop earrings and sleek heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts that lead to the back
    • Floor-length, form-hugging fit
    • Ribbed cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4079

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Flirty Floral Mini Dress

    This flirty floral mini dress is a must-have for summer parties! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a back zipper closure, ruched detailing, and a short, form-hugging fit. Style this dress with a chic charm necklace and wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Back zipper closure
    • Ruching
    • Mini-length, curve-hugging silhouette
    • Mesh fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1497

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun And Flirty Skater Dress

    This adorable skater dress will bring all the fun and flirty vibes to your party look! It features a sleeveless square neckline, ruffled spaghetti straps, and a cute fit and flare skater silhouette. Style this dress with hoop earrings and wedges.

    Fit & Features

    • Sleeveless square neckline
    • Ruffled spaghetti straps
    • High waist, skater silhouette
    • Cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4170

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy In Tie-Dye Mini Dress

    You'll be the trendy member of your squad in this casual tie-dye knit mini dress. It features a sleeveless crew neckline, tank shoulder straps, an exposed seam that runs down the center, and a short, curve-hugging fit. Style this dress with booties for an edgy vibe.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Center exposed seam
    • Mini-length, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4175

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Vibes Tie-Dye Mini Dress

    Bring the good vibes to your summer style with this adorable tie-dye mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, front ruched detailing, and a mini-length, curve-hugging silhouette. Complete the look with clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Ruching
    • Short, form-hugging fit
    • Mesh fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0784

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Heat Maxi Dress

    Bring the heat to your next vacay in this tropical printed maxi dress! It features an off-the-shoulder neckline, a flowy overlay with short sleeves, a high waist, a floor-length silhouette with a relaxed fit, and a thigh-high side slit. The all-over tropical palm leaf print is perf for your summer getaway! Style this dress with strappy sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Flowy overlay with short sleeves
    • High waist
    • Floor-length silhouette, relaxed fit, high side slit
    • Knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0778

    Category Name: Casual Dresses

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Linen Skater Dress

    Planning a weekend getaway? Don't forget to pack this adorable linen dress for an effortlessly chic look. The dress features a sleeveless V-neckline, halter spaghetti straps, a tie-back detail, a high waist, and a flirty and flowy skater silhouette. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps
    • Tie-back detail
    • High waist
    • Flowy skater skirt
    • Linen fabric
    • Runs true to size

    Style Number/Barcode: 05102-1085

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Flirty Ditsy Floral Skater Dress

    Cute and flirty, this ditsy floral skater dress is a summer staple! It features a strapless square neckline and a drop waist skater skirt silhouette. Style this dress with wedges for weekend brunch with the girls.

    Fit & Features

    • Strapless square neckline
    • Drop waist skater skirt silhouette
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-4177

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Sultry Strapless Bodycon Midi Dress

    Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down!

    Fit & Features

    • Brushed knit double-lined stretchy knit fabric
    • Strapless neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000034

    Category Name: Casual Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Sale