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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Trendy Twist Cutout Mini Dress
Trendy with a twist...you'll totally fall for this mini dress featuring a sleeveless, v-neck, spaghetti straps, a cutout bodice, side ruched seams, on knit-lined fabric with a form-hugging fit and moderate stretch. Complete the look-in mules for a daytime event.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Twist front accent
- Cutout bodice
- Side ruched seams
- Form-hugging fit
- Knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4657
Category Name: Casual Dresses
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Vacay Satin Ruched Tie-Back Dress
Planning a weekend vacay? Don't forget to pack this adorable satin dress! It features spaghetti straps and a ruched bust, a mini-length hem, and an open back with self-tie detail. Complete the look chic mules.
Fit & Features
- Sleeveless, spaghetti straps
- Ruched bust
- Mini-length hem
- Open back with self-tie
- Satin fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1276
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picture Perfect Marble Print Dress
This marble print mini dress is picture-perfect for snapping an insta-worthy shot! It features a sleeveless, square neck, spaghetti straps, side ruched seams, and a form-hugging fit on stretchy-lined knit fabric. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless, square neck
- Spaghetti straps
- Side ruched seams
- Form-hugging fit
- Lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4611
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Feels Halter Skater Dress
Feel flirty in floral! This adorable halter skater dress will add funky freshness to your summer lineup. It features a sleeveless smocked bodice, open-back with elasticized lattice straps, and a flowy short-length hem. Complete the look in strappy heels for a birthday brunch.
Fit & Features
- Sleeveless, halter neck, tie closure
- Smocked bodice
- Open-back, elasticized lattice straps
- Skater silhouette
- Flowy short-length hem
- Floral print, non-stretch woven fabric, knit lining
- Fits true to size
Style Number/Barcode: 05102-4707
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Neutral Vibe Mini Dress
Showcase a chic neutral vibe in this trendy ribbed knit mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, bold waist cutouts leading to an alluring open back with a cross-back strap design, and a short, curve-hugging silhouette. Style this dress with clear mules.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Waist cutouts, open back, cross-back strap design
- Mini-length, form-fitting, bodycon silhouette
- Double-lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4558
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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More To Come Tube Skater Dress
Perfect for day or night fun, this tube mini dress features playful ruffles that add a flirty touch while the skater silhouette flatters every figure with a fun, twirl-worthy flare.
Fit & Features
- Lined knit fabric, high stretch
- Strapless tube neckline
- Skater silhouette
- Ruffled mini-length hem, lace trimming
- Runs true to size
Style Number/Barcode: 05102-000220
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Neutral Tie-Dye Mini Dress
You'll fall in love with the trendy neutral tones of this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back, lace-up design, and a short, curve-hugging fit. The soft brushed knit fabric offers plenty of stretch. Style with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cross-back, lace-up design, tie closure
- Mini-length, form-fitting silhouette
- Neutral tie-dye pattern
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4645
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Babe Cutout Mini Dress
For looking and feeling like a total babe. Let your legs out in this sleeveless mini dress featuring an on-trend square neck, spaghetti straps, a cutout bodice, side ruched seams and a bodycon fit. Complete the look in strappy heels for a party.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Cutout bodice
- Bodycon fit, side ruched seams
- Mini-length hem
- Textured knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4545
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty In Floral V-Neck Mini Dress
Flirty in floral! Go forth and bloom for summer in this mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, a form-fitting silhouette, and a front slit along the hem. Complete the look in doorknocker earrings and heels.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Form-fitting silhouette
- Front slit
- Mini-length hem
- Ditsy floral print, stretchy knit fabric
- Fits true to size
Style Number/Barcode: 05102-4530
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sandy Toes Crochet Bodysuit Dress
The perfect long dress to walk the sandy beaches! This crochet maxi features a sleeveless, V-neck, adjustable spaghetti straps, dual front hoop inserts, and a bodysuit lining with dual-snap button closure on a cheeky bottom. Complete the look in boho earrings and a bracelet.
Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Dual front hoop inserts
- Bodysuit lining, dual snap-button closure, cheeky bottom
- Form-fitting silhouette
- Maxi-length hem
- Sheer crochet fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4675
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Muse Asymmetrical Midi Dress
Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Midi-length, asymmetrical hem, ruching down one side
- Form-fitting silhouette
- Geometric multi-print pattern
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4644
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beachside Beauty Floral Mini Dress
You'll be a total beachside beauty on your summer vacay in this floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, dual front verticals seams with ruched detailing, and a short, curve-hugging silhouette. The lined mesh fabric features an all-over tropical floral print. Complete the look with espadrille sandals.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Dual front vertical seams, ruched detailing
- Mini-length, form-fitting, bodycon silhouette
- Tropical floral print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4609
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gimme Love Texture Knit Mini Dress
Make em' fall for you in this curve-hugging mini dress featuring a sleek, sleeveless square neck, and bungee spaghetti straps, and is composed of texture-knit fabric with plenty of stretch. Complete the look in strappy mules.
Fit & Features
- Sleeveless, square neck, bungee spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Texture-knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4507
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Darling Chiffon Ruffle Mini Dress
Serving darling vibes on repeat. This floral mini dress is your go-to for twirling through summer plans, from picnics to shower celebrations—basically, anytime you wanna feel effortlessly pretty.
Fit & Features
- Floral print, chiffon lined fabric
- V-neckline, ruffle trim
- Adjustable spaghetti straps
- Side zipper and hook-eye closure
- Ruffled trim throughout
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000592
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Jungle Queen Leopard Satin Slip Dress
Clearly, you're the queen of the jungle in this leopard satin mini! It features sleek, adjustable spaghetti straps, a v-neckline, and a slightly flared hem with a slit accent. Composed of a luxe satin-lined fabric with no stretch. Style with chic block heels.
Fit & Features
- Sleeveless, V-neckline
- Sleek adjustable spaghetti straps
- Slit accent, Back zipper closure
- Slightly flared hem
- Leopard pattern
- Luxe satin-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-1461
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Bow Ruffled Short Dress
Flaunt your flirty self and bow in this short dress featuring a sleeveless, square neck, adjustable spaghetti straps, a partial open-back with bow-tie closure, and a tiered ruffle hem. Complete the look in a choker necklace and mules.
Fit & Features
- Sleeveless, square neck
- Adjustable spaghetti straps
- Partial open-back, bow-tie closure
- Tiered ruffles
- Short-length hem
- Fits true to size
Style Number/Barcode: 05102-4457
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Disco Diva Square Neck Mini Dress
Get down at the disco looking like a diva in this fab retro mini dress featuring a sleeveless, square neck, bungee spaghetti straps, side ruched seams, on a knit-lined fabric with a form-hugging fit. Complete the look in platform heels for a dance party.
Fit & Features
- Sleeveless, square neck
- Bungee spaghetti straps
- Side ruched seams
- Form-hugging fit
- Mini-length hem
- Retro print, knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4529
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Under The Palms Halter Skater Dress
Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Side cutouts, strappy banded back design, tie closure
- Smocked high waist, flowy skater skirt
- Tropical palm leaf print
- Gauze fabric, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4499
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Palisades Ruched V-Neck Midi Dress
Let the sun kiss your shoulders in this flowy midi dress! It features a sleeveless ruched v-neck and spaghetti straps that lead to the sultry open-back with a lace-up closure. Complete the look in trendy sandals.
Fit & Features
- Sleeveless, ruched v-neck, spaghetti straps
- Flowy midi-length silhouette
- Open-back, lace-up closure
- Gauze woven fabric
- Inner lining
- Fits true to size
Style Number/Barcode: 05102-4456
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Express Yourself O-Ring Bandeau Midi Dress
Express your stylishly bold self in this midi dress! It features a strapless, bandeau top with a string tie o-ring, cutout bodice, and midi bodycon skirt with a sultry side slit. Composed of ribbed knit fabric with a moderate stretch. Finish the look in oversized sunglasses.
Fit & Features
- Strapless bandeau top
- String tie o-ring, cutout bodice
- Midi bodycon skirt
- Side slit
- Ribbed knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06005-1263
Category Name: Casual Dresses
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Retro Muse Satin Slip Dress
You'll be a total retro muse in this sleek satin slip dress! It features a sleeveless V-neckline with a tie-front bodice, adjustable spaghetti straps, a short, A-line silhouette, and an all-over multi-colored swirl print pattern. Style this dress with hoop earrings and clear mules.
Fit & Features
- Sleeveless V-neckline, tie-front detail, small cutout
- Adjustable spaghetti straps
- Mini-length, A-line silhouette
- All-over multi-colored swirl print
- Woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4665
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chain Reaction Rib Knit Dress
This rib knit dress may cause a chain reaction of followers! It features a sleeveless square neckline, edgy chain-link straps, and a bodycon mini-length hem. Complete the look in platform heels for girl's night.
Fit & Features
- Sleeveless square neckline
- Chain-link shoulder straps
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4480
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Miami Nights Bodycon Mini Dress
Take on the night scene with your squad in this stunning printed mini dress. It features a sleeveless V-neckline, spaghetti straps, a dual twist-front design with waist cutouts for an alluring vibe, and a short, curve-hugging, bodycon silhouette. The stretchy knit fabric features an all-over geometric floral pattern. Complete your look with strappy stilettos.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual twist-front design, waist cutouts
- Mini-length, form-fitting silhouette
- Geometric floral pattern
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4498
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boogie On Down Lace-Up Mini Dress
Boogie all over town in this retro mini dress featuring a sleeveless, square neck, spaghetti straps, a trendy lace-up on the back, bodycon silhouette, on swirl marble print knit fabric with a moderate stretch. Complete your groovy fit with strappy stiletto heels.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Lace-up back
- Bodycon silhouette
- Mini-length hem
- Swirl marble print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4688
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free