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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Alluring Accents Bodycon Mini Dress
You'll love the alluring accents of this trendy-chic bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, a revealing side cutout at the waist, ruching down one side with an adjustable drawstring, and a short, curve-hugging fit. The smooth knit fabric features an all-over snake print pattern. Style this dress with clear heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side cutout at the waist
- Ruching down one side, adjustable drawstring
- Bodycon silhouette, mini hem
- Snake print, lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4473
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feel The Heat V-Neck Midi Dress
Sizzle and stun in this midi dress perf to bring up the temps! It features a sleeveless plunge V-neckline with a center O-ring insert, cutout bodice, form-fitting silhouette, and a side slit accent. Complete the look in lucite mules for a night out.
Fit & Features
- Sleeveless, plunge V-neck
- Center O-ring
- Cutout bodice
- Form-fitting silhouette
- Side slit accent, midi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1448
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One Love Sweetheart Sweater Dress
The sweater dress your wardrobe needs! It features a sleeveless, sweetheart neckline, shoulder straps, a ruched bust seam, and a flirty cutout waist leading to the bodycon, mini-length silhouette. Complete the look in statement earrings.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, sweetheart neckline, shoulder straps
- Ruched bust seam
- Cutout waist
- Bodycon silhouette
- Mini-length hem
- Hacci ribbed-knit fabric
- Runs true to size
Style Number/Barcode: 05102-4751
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hardrock Babe Graphic Short Dress
You're with the band. Enter backstage in this edgy babe-status graphic short dress featuring a strapless bodice, lace-up bungee straps, flexible boning inserts, side denim panels with seam detail, and a front script that reads, "Make Some Noise/ Hardrock" and a form-fitting short hem. Complete the look in a ring set.
Fit & Features
- Strapless tube bodice
- Lace-up bungee straps, flexible boning inserts
- Side denim panels, seam detail
- A font script reads, "Make Some Noise/ Hardrock"
- Form-fitting, short-length hem
- Minimal stretch
- Fits true to size
Style Number/Barcode: 06002-1222
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take Me On A Getaway Midi Dress
You'll be ready for a fab weekend getaway in this curve-hugging midi dress! It features a sleeveless sweetheart neckline with halter straps, chic waist cutouts, and a midi-length, form-fitting silhouette with a thigh-high side slit. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless sweetheart neckline
- Halter spaghetti straps, tie at the back of the neck
- Waist cutouts
- Midi-length, form-fitting silhouette, high side slit
- Textured ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4687
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bae-cation Palm Print Mini Dress
Look and feel like a total bae on vacay! This tropical mini dress is essential for exploring the island in style. It features a sleeveless, square neck, adjustable spaghetti straps, side ruched seams, and a brushed knit fabric offering a form-hugging fit and moderate stretch. Complete the look in espadrille wedges and earrings.
Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Side ruched seams
- Form-hugging fit
- Mini-length hem
- Palm print, brushed knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4557
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Light Sweater Midi Dress
Keep your look light and effortless in this sweater midi dress perfect for any day or night summer event! It features a sleeveless, v-neck, spaghetti straps, a bodycon silhouette, and a sultry front slit. Complete the look in strappy sandals.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1420
Category Name: Casual Dresses
Price: $16.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Drama Abstract Mesh Maxi Dress
The kind of dress that makes an entrance before you even say hello. With an abstract print, sultry cutout back, and daring front slit, it’s made for statement moments only.
Fit & Features
- Abstract print, airy mesh fabric, partial knit lining
- Strapless tube neckline
- Cutout back
- Front slit
- Curve-hugging, maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000320
Category Name: Casual Dresses
Price: $10.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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One Night Of Chic Mesh Maxi Dress
Have your chic moment in this mesh maxi dress featuring a sultry, one-shoulder neckline, a partial open-back, side and back ruching, and an asymmetrical maxi-length hem with a side slit cutout. Complete your dressy look in sleek heels.
Fit & Features
- Sleeveless, one-shoulder neckline, spaghetti strap
- Partial open-back
- Side and back ruching
- Side slit cutout
- Asymmetrical maxi-length hem
- Form-hugging fit, partial lining, mesh fabric
- Fits true to size
Style Number/Barcode: 05102-4736
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lush Paradise Lace-Up Mini Dress
Escape to a lush paradise in this tropical mini dress perf for your next island vacay! Featuring a sleeveless, square neck, spaghetti straps that lead to the open-back with a lace-up design, a bodycon silhouette, and palm print knit-lined fabric. Complete the look in sunglasses and heels.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back, lace-up design
- Bodycon silhouette
- Mini-length hem
- Palm print, stretchy knit-lined fabric
- Fits true to size
Style Number/Barcode: 05102-4516
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Palm Perfect Tropical Midi Dress
Look perfect in paradise wearing this palm print midi dress featuring a sleeveless, v-neck, spaghetti straps, a form-fitting silhouette, and a front slit accent on stretchy knit fabric. Complete your vacation look in wedges.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Form-fitting silhouette
- Front slit accent
- Midi-length hem
- Palm print, knit fabric with moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4542
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marble Muse Mesh V-Neck Midi Dress
Be your own muse! This marble mesh dress will become your new fave for cocktail soirees and evening dinner parties. It features a sleeveless, v-neck, adjustable criss-cross spaghetti straps, a bodycon silhouette, side ruched seam atop an asymmetrical hem. Complete the look with dangly earrings and heels.
Fit & Features
- Sleeveless, v-neck
- Adjustable criss-cross spaghetti straps
- Bodycon silhouette
- Side ruched seam
- Asymmetrical midi hem
- Marble print, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4515
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paisley Queen Ruched Mini Dress
Enchant them all in your love for all things paisley! This square neck mini dress features a sleeveless bodice, spaghetti straps, a bodycon silhouette, and a front ruched seam on stretchy knit fabric. Complete the look in espadrille wedges.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Bodycon silhouette
- Front ruched seam
- Mini-length hem
- Paisley print knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4650
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Timeless Twist One Shoulder Dress
Bring the allure in this one-shoulder maxi dress featuring a sleeveless bodice, a single spaghetti strap, and a form-hugging silhouette atop an asymmetrical slit hem with a timeless twist accent. Complete the look in dangly earrings and heels.
Fit & Features
- Sleeveless, one-shoulder
- Single spaghetti strap
- Form-hugging silhouette
- Twist accent and slit
- Asymmetrical maxi-length hem
- Slinky knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4714
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nothing But Sultry V-Neck Midi Dress
You'll be nothing but sultry in this midi dress for a party! It features a sleeveless, v-neck, bungee spaghetti straps, cutout bodice, open-back with tie closure, form-fitting silhouette, and a side slit accent along the hem. Complete the look with a sparkly bracelet and heels.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Open-back, tie closure
- Cutout bodice
- Form-fitting
- Side slit, midi-length hem
- Slinky knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4724
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Summer Mood Knit Mini Dress
This stretchy ribbed knit mini dress is perfect for those casual summer days. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing down the side seams with adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Style with cute slides.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Ruching down the side seams, adjustable drawstrings at the hem
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4685
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet For You Marble Mesh Mini Dress
This mesh mini dress will look so good and so sweet in your lineup! It features a sleeveless square neckline, adjustable spaghetti straps, a short, curve-hugging, bodycon silhouette, and an all-over marble print on a lined mesh fabric. Complete your cool summer look with strappy heels.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Mini-length, form-fitting, bodycon silhouette
- Marble print
- Sheer mesh fabric, knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4568
Category Name: Casual Dresses
Price: $6.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Beauty Tropical Maxi Dress
Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.
Fit & Features
- Sleeveless, square neck, halter straps
- Open-back with tie
- Bodycon silhouette
- Front twist accent and slit
- Maxi-length hem
- Tropical palm print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4720
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Times Marble Halter Dress
Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.
Fit & Features
- Halter neckline, ruched drawstring, tie closure
- Cutout bodice
- Form-hugging fit
- Mini-length hem
- Marble print knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4531
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hot And Cold Sweater Mini Dress
Sweaters may be for cold weather but this mini dress is too hot not to be seen this summer! It features an off-the-shoulder neckline, short sleeve cuffs, a form-fitting silhouette, and a mini-length hem on stretchy rib-knit fabric. Complete the look in platform heels.
Shop More Sweater Styles: Shop The Collection
Fit & Features
- Off-the-shoulder neckline
- Short sleeve cuffs
- Form-fitting silhouette
- Mini-length hem
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1423
Category Name: Casual Dresses
Price: $7.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Resort Ready Palm Print Mini Dress
You'll be ready for your getaway at the resort with this tropical mini dress in your arsenal! It features a sleeveless square neck, sleek spaghetti straps, a palm print, and a curve-hugging silhouette. Complete your vacay look in espadrille wedges.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Palm print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4681
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Garden Tease Floral Tube Maxi Dress
She’s sweet from afar—but up close? Full body-con bombshell. This floral maxi dress is made for occasions you don’t want to forget.
Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Tube neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000511
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Fridays Halter Midi Dress
Bring the heat this summer in this sultry midi dress on a Friday night out! It features an off-the-shoulder, halter neckline, a cinched bust with cutout accents, a form-fitting silhouette, and a flirty side slit. Complete the look in strappy mules.
Fit & Features
- Off-the-shoulder, halter neckline
- Cinched bust, cutout accents
- Form-fitting silhouette
- Side slit, midi hem
- Texture knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4444
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Energy Marble Mesh Dress
Radiate major stylish energy in this marble print mini dress featuring a sleek, sleeveless square neck with bungee spaghetti straps, a bodycon silhouette, and a sheer mesh overlay with lining. Complete the look braid strap mules.
Fit & Features
- Sleeveless, square neck, bungee spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Marble print
- Sheer mesh overlay, lining
- Fits true to size
Style Number/Barcode: 05102-4523
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale