Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and your calendar.
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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.
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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