Casual Dresses

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Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • 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
  • Absolute Bombshell Cutout Mini Dress

    This sultry mini dress will have you looking like an absolute bombshell! It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to a back cutout, and a mini-length, curve-hugging silhouette. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts that lead to a back cutout
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4166

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale