Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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Cutest Plans Floral Eyelet Corset Skater Dress
Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.
Fit & Features
- Floral eyelet woven fabric, tulle and knit linings
- Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
- Underwire bust support
- Tie-shoulder straps, side zipper and hook-eye closure
- Corset bodice with boning, V-shaped waist, ruffled trim
- Lace-up back design, short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000130
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Chic Sleeveless Midi Dress
Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!
Fit & Features
- Woven fabric
- Boat neckline
- Low-cut back
- Drop waist seam
- Flowy silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000164
Category Name: Casual Dresses
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Girly Gingham Print Ruffled Mini Dress
You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.
Fit & Features
- Smocked cotton fabric, high stretch
- Gingham print
- Sleeveless sweetheart neckline, ruffled trim, small bow detail
- Adjustable spaghetti straps
- Mini-length ruffled hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-000160
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Corset Cutie Denim Mini Dress
From brunch dates to fun at the fair, she always eats. This skater denim mini dress serves flirty and fierce with a corset bodice and sweet bust tie that gives major retro babe energy.
Fit & Features
- Denim fabric, lace trim woven lining
- Corset-style bodice with lace paneling, flexible boning
- Sweetheart neckline, bust tie, lace trim, underwire bust
- Adjustable lace trim shoulder straps
- Back lace-up detail, zipper and hook-eye closure
- Drop waist skater skirt with lace trim, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000157
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lowkey Head Turner Open Back Mini Dress
She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.
Fit & Features
- Rib knit fabric, smooth, stretchy knit lining
- Crew neck
- Open back with tie detail
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000768
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: BROWN-2
Available Size: XS, S, M, L
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Island Afterglow Knit Maxi Dress
Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.
Fit & Features
- Texture knit fabric, smooth knit lining
- Plunge V-neckline, hardware insert
- Long bell sleeves
- Cutout bodice, open back
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000155
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Summer Vibe Polka Dot Satin Mini Dress
This polka dot satin mini dress will bring that sweet summer vibe featuring a dainty lace trim, halter V-neckline, and a short A-line silhouette. Style with sneakers for a casual look.
Fit & Features
- Satin woven fabric, sheer lace trim
- Polka dot print
- Sleeveless V-neckline
- Halter straps with tie-back design, open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000156
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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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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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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Match My Energy Eyelet Skater Dress
This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.
Fit & Features
- Eyelet fabric, sewn-in knit lining
- Strapless neckline
- Strappy back
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000108
Category Name: Casual Dresses
Price: $9.97 $65.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Realness Denim Cutout Maxi Dress
Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.
Fit & Features
- Denim fabric, sewn-in knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Cutout bodice design, hoop insert
- Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
- Ruffled tiered maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000131
Category Name: Casual Dresses
Price: $30.97 $68.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Allure A-Line Mini Tube Dress
Show off a flirty allure in this adorable mini tube dress designed with a strapless straight neckline, drop waist, and a short, tiered, A-line silhouette. Style with sneakers for a cute and casual 'fit.
Fit & Features
- Lined knit fabric, high stretch
- Elasticized strapless straight-across neckline
- Ruched side seams
- Drop waist design
- Mini-length tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000130
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Effortlessly Sweet A-Line Mini Dress
Proof that effortless can still be everything. This scoop neck mini dress hugs your curves with a sleek A-line fit—perfect for date night, birthday dinners, or dressy occasions!
Fit & Features
- Structured woven fabric, bust lining
- Scoop neckline, padded bra cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-Line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000104
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Time To Vacay Halter Lace-Up Maxi Dress
Your next vacay fit is here - say aloha to this knit maxi dress designed to showcase your curves in a bodycon fit and bare some skin with the alluring lace-up back.
Fit & Features
- Texture knit fabric, knit lining, moderate stretch
- High halter neckline
- Spaghetti straps
- Lace-up back
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000053
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All This Allure Strappy Halter A-Line Skater Dress
You'll be irresistible in this A-line skater dress on a night out! This stunning dress features a plunging halter neckline and a strappy back, adding a touch of allure to any occasion, while the mini-length hem offers a flirty touch.
Fit & Features
- Smooth knit fabric, stretchy knit lining
- Plunge halter neckline, bar accent, tie straps
- Strappy back with spaghetti strap tie
- A-Line skater silhouette
- Seam detailing, mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000697
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut It Out Babe Midi Dress
Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.
Fit & Features
- Stretchy rib knit fabric, contrast trim
- Square neck, tank shoulder straps
- Cutout bodice
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000045
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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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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So Perfect Collar Short Sleeve Mini Dress
There's nothing more perfect for warmer temps than this rib knit mini dress for an effortless athleisure vibe! This bodycon dress features a chic collar and short sleeves making it ideal for sunny days while the subtle side slit adds a flirty look.
Fit & Features
- Rib knit stretchy fabric
- Collar V-neckline
- Short sleeves
- Bodycon silhouette
- Side slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000127
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casually Cute Ribbed Knit Strapless Mini Dress
Casually cute, this strapless mini dress is perfect for styling from coffee dates to happy hour. The A-line fit adds a flirty flair to the short silhouette.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000123
Category Name: Casual Dresses
Price: $14.97 $34.90
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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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