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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Cute Little Things Striped A-Line Mini Dress
Show off your cute self in this striped mini dress for any summer occasion! The playful ruffle details add movement and feminine charm, while the flattering A-line silhouette hugs your curves in all the right places.
Fit & Features
- Striped print, cotton-blend lined fabric
- Sweetheart neckline
- Adjustable spaghetti straps
- Stretchy smocked bodice
- A-Line silhouette, ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000106
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Inspired Art Abstract Bodycon Mini Dress
Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments!
Fit & Features
- Abstract print, mesh-lined fabric
- Adjustable spaghetti straps
- Square neckline, padded bra cups
- Front ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-5952
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner By The Sea Tube Crochet Midi Dress
You'll be a dreamy view in this crochet tube midi dress, enjoying a dinner by the sea. The form-hugging silhouette showcases your figure while the high side slit adds a daring touch of allure with seashell trim creates a captivating coastal-inspired look.
Fit & Features
- Crochet knit fabric, short knit stretchy lining
- Strapless tube neckline
- Form-hugging fit
- High side slit, seashell trim
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000109
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Stunner Floral Mesh Strapless Maxi Dress
Turn heads your next vacay in this bold floral mesh maxi dress made to impress. The long bodycon silhouette will flaunt your gorgeous curves.
Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Large floral print
- Strapless straight neckline
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-4149
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sent A Postcard Lace-Up Print Mini Dress
A chic printed mini dress for your next cute trip! This dress is designed to turn heads with a lace-up back that adjusts to your perfect fit, statement puff sleeves, and a form-hugging fit that showcases your curves.
Fit & Features
- Printed design, woven fabric, woven lining
- Puff short sleeves
- Sweetheart neckline
- Lace-up back, lower zipper and hook-eye closure
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000113
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Jetset Babe Tropical Print Belted Maxi Dress
Jetset to somewhere fabulous in this tropical print maxi dress! The flattering belted waist cinches your silhouette while hidden side pockets add convenience. A sultry side slit creates movement for a trendy look.
Fit & Features
- Tropical multi-print, woven fabric
- Strapless neckline
- Belted waist
- Hidden side pockets
- Flowy maxi silhouette, side slit
- Runs true to size
Style Number/Barcode: 05102-000112
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Best Yet Sleeveless Crew Neck Slit Maxi Dress
The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!
Fit & Features
- Soft knit fabric, short lining, plenty of stretch
- Sleeveless crew neckline
- Tank straps
- Side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5588
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Striking A Pose Halter Cutout Mini Dress
Stunning textured knit adorns this sultry bodycon mini dress with a high halter neck and cutout side accent that reveals a peak of skin!
Fit & Features
- Texture knit fabric, smooth stretchy knit lining
- High halter neckline, spaghetti strap tie
- Side cutout
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000114
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Falling In Love V-Neck Lace A-Line Mini Dress
Fall in love with how you'll look in this lace a-line mini dress for every romantic spree!
Fit & Features
- Lace-lined fabric
- V-neckline with ribbon bow trim
- Adjustable spaghetti straps
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000017
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Dreaming Strapless Cutout Ruffle Mini Dress
Take a trip downtown or somewhere new in this strapless abstract print dress! With a cutout back, form-hugging fit, and ruffled mini hem, it's the ultimate look for summer.
Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Strapless neckline
- Cutout back
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000110
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wow Factor Cutout Maxi Dress
In this strapless maxi dress, you'll be checking yourself out in every mirror you pass! It boasts a metal square accent with a chic drape, a cutout bodice to show some skin, and a high front slit for effortless movement.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Strapless sweetheart neckline, metal square accent, drape design
- Padded bra cups
- Cutout bodice, back zipper and hook-eye closure
- High front slit
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000116
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Turn Up The Heat One-Shoulder Cutout Midi Dress
Turn up the heat in this sultry knit midi dress designed with a one-shoulder neckline, front cutouts, sleek O-ring accents, and a high-cut side slit. The bodycon fit will highlight your gorgeous curves.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Sleeveless asymmetric one-shoulder neckline, gold metal O-ring accent, tank strap
- Dual front cutouts under the bust and above the waist, gold metal O-ring accent
- Ruching
- Midi-length hem, thigh-high side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000117
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Fave High Slit Maxi Dress
Show off effortless style in this breezy gauze maxi dress designed with a smocked waist, high front slit, and flowy A-line silhouette. Perf for summer parties, pair with espadrille sandals.
Fit & Features
- Gauze woven fabric, stretchy knit lining
- Sleeveless V-neckline, spaghetti straps
- Open cross-back tie-back design
- Smocked high waist
- Tiered design, thigh-high front slit
- Maxi-length hem, flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000121
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Memories Tie-Back Babydoll Mini Dress
Make sweet memories at showers or graduations in this cute babydoll mini dress with a flirty tie-back and flowy hem.
Fit & Features
- Woven fabric
- Sweetheart neckline, wide shoulder straps
- Tie-back design
- Babydoll silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000120
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Bloom Strapless Lace-Up Floral Maxi Dress
With the warmer months ahead it's time to bloom in this floral maxi dress perf for vacations and weekend getaways! The dress boasts an eye-catching lace-up back and a mermaid silhouette that accentuates your natural curves.
Fit & Features
- Floral print, knit fabric lined with stretchy knit
- Lace-up back
- Mermaid silhouette
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4080
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Charm Striped Knit Strapless Midi Dress
Show up with that chic charm in this striped knit midi dress designed with a strapless straight neckline and a curve-hugging bodycon fit.
Fit & Features
- Ribbed knit fabric, high stretch
- Striped print
- Strapless straight neckline
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-2222
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Poise Button Bodycon Midi Dress
Polished and poised, this sweet sleeveless midi dress will elevate your everyday style with chic button accents and a bodycon fit.
Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Wide shoulder straps
- Button accents, front faux pockets
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2261
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heat Check Abstract Cutout Maxi Dress
This isn’t just a dress, it’s a moment. With sultry cutouts, strappy details, and a leggy high slit, this curve-hugging mesh maxi brings the heat for nights out, birthdays, and turning heads on vacation!
Fit & Features
- Abstract tie-dye print, mesh fabric, sewn-in knit lining
- One-shoulder neckline, bungee spaghetti strap
- Side cutout, open back
- High front slit, adjustable bungee cord strap with toggle
- Hidden side zipper and hook-eye closure
- Curve-hugging fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000125
Category Name: Casual Dresses
Price: $19.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Obsessed With The Vibe Fringe Lace Mini Dress
A lace mini dress for when the girls' trip makes it out of the group chat! The playful fringe long sleeves create movement with every gesture, while the strappy open back design reveals just enough skin to turn heads.
Fit & Features
- Lace pattern, soft velvet-like fabric, stretchy knit lining
- Sheer fitted long sleeves with fringe trim
- V-neckline, keyhole cutout bust tie
- Strappy open back with tie
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000122
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Effortless Tie-Front Ruffled Skater Dress
Make your weekend outfits so effortless with this adorable tie-front skater dress. The lightweight gauze fabric paired with the ruffled skater silhouette creates that breezy, flowy fit you'll love.
Fit & Features
- Gauze woven fabric with smooth woven fabric, no stretch
- Sleeveless V-neckline, padded bust, bust tie accent, keyhole cutout
- Adjustable spaghetti straps
- Partially smocked back
- High waist seam
- Short skater silhouette, tiered ruffled design
- Runs true to size
Style Number/Barcode: 05102-6027
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Boho Bell Sleeve Knit Mini Dress
Live out those dreamy boho vibes in this breezy knit mini dress featuring a plunging V-neck with beaded bust tie accents, sheer long bell sleeves, and an open back with a tie-back design.
Fit & Features
- Sheer textured knit fabric, partial knit lining
- Plunging V-neckline, dual bust ties with beaded detailing
- Sheer long bell sleeves
- Open back, tie-back spaghetti straps
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000129
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Sunny Days Crew Neck Poplin Midi Dress
This sleeveless midi dress was made for romantic sunny days! It features a classic crew neck and a flattering drop waist seam that accentuates your figure along the A-line silhouette.
Fit & Features
- Stretchy rib knit fabric, poplin woven fabric, stretchy knit lining
- Crew neck
- Drop waist seam
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000136
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Serve Abstract Print Mesh Bodycon Mini Dress
Show off a sultry serve in this abstract print mesh mini dress designed with a strapless neckline and a bodycon fit to flaunt your curves.
Fit & Features
- Sheer mesh fabric, full-length knit lining, high stretch
- Abstract print
- Strapless straight-across neckline
- Ruching
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000133
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Cutie Halter Ruffle Mini Dress
Make this halter mini dress a staple this season! The form-hugging silhouette accentuates your curves in all the right places, while the playful ruffled hem adds flirty movement. Style with strappy heels.
Fit & Features
- Texture knit fabric, moderate stretch
- Cowl neckline
- Spaghetti straps with hoop inserts
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000132
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale