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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Caught Daydreaming Polka Dot Mini Dress
Serving flirty little getaway vibes in this polka dot dress! It features a breezy blouson fit and a tiered ruffle skirt that moves perfectly from brunch to spontaneous plans.
Fit & Features
- Polka dot print, mesh fabric, smooth lining
- Strapless tube neckline
- Blouson relaxed bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000716
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Endless Summer Open Back Mini Dress
An easy silhouette with just the right amount of detail. The summer mini dress pairs a relaxed shape with a bold velvet burnout pattern and an open-back finish for effortless impact. Add it to your lineup for brunch, vacation plans, or casual days out.
Fit & Features
- Burnout velvet pattern, partial knit lining, mesh fabric
- Boat neckline
- Short sleeves
- Open back with tie closure
- Relaxed shift fit
- Mini-length fitted hem
- Runs true to size
Style Number/Barcode: 05102-000712
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Ocean Air Mood Halter Maxi Dress
This is the kind of dress that makes every plan feel a little more exciting. The soft hue, textured fabric, and waist cutouts bring just the right amount of drama for beachside dinners, cocktails, and those nights that somehow turn into your favorite memories.
Fit & Features
- Texture knit fabric, knit lining
- Sweetheart halter neckline, tie strap, non-slip grip lining
- Hoop insert and cutout bodice and back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000714
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: L
Product Badge:- Sale
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Wild Invite Mesh Mini Dress
Your calendar just got louder. This animal print mesh bodycon mini dress brings a sleek crew neckline, sleeveless cut, and a bodycon fit made for parties, concerts, and night out plans that need bite.
Fit & Features
- Animal print, mesh fabric, sewn-in knit lining
- Sleeveless crew neckline
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000711
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BLACK, IVORY, PRINT, BLACK-2, BLACK-3
Available Size: XS, S, M, L
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Curve Tease Cutout Mini Dress
A little sleek, a little daring, fully ready for plans. This strapless mini dress hugs the figure with a bodycon fit and front cutout that effortlessly flaunts your figure.
Fit & Features
- Soft rib knit sweater fabric with stretch
- Contrast trim strapless neckline
- Front cutout with contrast trim
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000382
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Sale
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Kissed In Polka Dot Mesh Mini Dress
A little playful, a little risky, and fully worth the attention. This polka dot mesh mini dress hugs in all the right places with a plunge halter neckline, open back, and layered ruffle hem that was made for stealing the scene.
Fit & Features
- Polka dot print, mesh fabric, knit lining
- Plunge halter neckline, tie straps
- Open back
- Side ruched seams, fitted bodice
- Layered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000709
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: S
Product Badge:- Sale
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Sweet On Plans Polka Dot Mini Dress
Caught mid-stroll and looking sweet in this polka dot dress. This dress hugs just right with a form-hugging fit and a flirty ruffle hem made for daytime plans.
Fit & Features
- Polka dot print, knit, stretchy fabric
- One-shoulder neckline
- Form-hugging ruched fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000710
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: L
Product Badge:- Sale
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Island Time Floral Ruffle Dress
Your out-of-office reply just found its dress. With a vibrant tropical print, flirty cutout detail, and layers of playful ruffles, this mini dress was made for vacations, sunset cocktails, and every photo op in between.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter neckline, hardware insert, tie straps
- Keyhole cutout
- Form-hugging fit
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000706
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Heat Floral Chiffon Mini Dress
This floral mini dress is flirty, a little bold, and made for vacations, weekend plans, and showers. The halter tie and front cutout bring the drama, while the soft ruffles and A-line fit keep it balanced and feminine.
Fit & Features
- Floral print, chiffon-lined fabric
- Halter sweetheart neckline, tie straps
- Cutout side and back
- Ruffled detailing
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000708
Category Name: Casual Dresses
Price: $35.00 $49.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: L
Product Badge:- Sale
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Keep It Cute Bodycon Mini Dress
This one just feels like a good idea. A ruched tank mini dress that smooths and shapes with a barely-there feel, made for last-minute plans you’re definitely saying yes to.
Fit & Features
- Smooth knit-lined stretch fabrication
- V-neckline with tank straps
- All-over ruched detailing
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000704
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Endless Summer Abstract Maxi Dress
This dress looks like it was made for golden hour by the water. Featuring a dreamy abstract print, draped cowl neckline, and beaded halter straps, it brings effortless vacation energy to every RSVP.
Fit & Features
- Abstract print, mesh knit fabric, sewn-in knit lining
- Square halter neckline, beaded tie straps
- High side slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000811
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE-2
Available Size: XS, S
Product Badge:- Sale
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Going Somewhere Cute Mini Dress
The kind of dress you'll love this season. With a sculpting bodycon fit and all-over ruching, this mini dress keeps things sleek, flattering, and easy to dress up or down.
Fit & Features
- Stretchy knit fabric, double-lined
- Crew neck
- Short sleeves
- Ruched bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000703
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Striped Halter Bodycon Mini Dress
Stripes are back in rotation, and this dress makes the update feel effortless. The rib knit fabric and plunging halter neckline shape a sleek mini silhouette with a distinctly retro edge. Pair it with minimalist heels for a trend-forward going-out look.
Fit & Features
- Ribbed knit fabric with stretch
- Striped pattern
- Plunge halter neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000700
Category Name: Casual Dresses
Price: $19.96 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Sale
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Daydream Darling Babydoll Mini Dress
Your soft-girl moment just called. This puff sleeve mini dress features an open tie back and breezy cotton blend woven fabric that feels easy, romantic, and perfect for brunch, showers, and any weekend fun.
Fit & Features
- Cotton-blend woven fabric, woven lining
- Puff short sleeves
- Square neckline
- Open tie-back design
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000698
Category Name: Casual Dresses
Price: $45.90
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Vibes Strapless A-Line Mini Dress
This is your flirty little upgrade when you want to feel instantly put-together. The strapless A-line mini dress hugs up top, skims the body, and finishes with a playful ruffle that moves with you.
Fit & Features
- Brushed knit fabric, high stretch
- Strapless sweetheart neckline
- Drop waist, ruched detailing
- Tiered ruffled design
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000697
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: M, L
Product Badge:- Sale
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Bare Shoulder Mood Bodycon Midi Dress
Shoulders out, confidence locked in. This ribbed bodycon midi dress contours your shape with a foldover neckline that flaunts some skin. Perfect for showers, graduations, or any dressed-up plans.
Fit & Features
- Soft rib knit fabric
- Foldover off-the-shoulder neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000695
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise In Floral Midi Dress
The RSVP practically sends itself. This tropical floral midi dress features a breezy asymmetric hem and flattering halter neckline that was made for destination weddings, dinners, and vacation photos.
Fit & Features
- Abstract floral print, mesh-lined fabric
- Halter V-neckline
- Spaghetti straps
- Ruffled trim
- Flowy midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000813
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK-2
Available Size: XS, L
Product Badge:- Sale
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Good Things Coming Mini Dress
Featuring a draped cowl neckline, flirty front keyhole detail, and body-hugging fit, this mini dress was made for rooftop hotel bars, vacations, and night-out plans.
Fit & Features
- Knit fabric, high stretch
- Draped cowl neckline
- Adjustable straps
- Back strap detail
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000378
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, L
Product Badge:- Sale
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Last Minute Plans Striped Mini Dress
No outfit panic necessary—this mini dress does all the work for you. With a flattering draped neckline, playful striped design, and flirty asymmetrical silhouette, it's made for brunch, day dates, and spontaneous weekend plans.
Fit & Features
- Striped print, knit fabric, knit lining
- Cowl neckline
- Adjustable spaghetti straps
- Curve-hugging asymmetrical silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000693
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun Chaser Beaded Crochet Mini Dress
Vacation bag called. This beaded crochet mini dress is first on the list. The bodycon fit, halter neckline, and chic beaded details bring just enough drama for dinner plans, rooftop drinks, and every photo op.
Fit & Features
- Crochet knit fabric, knit lining, moderate stretch
- Sleeveless V-neckline, beaded trim under the bust
- Halter strap
- Open back
- Mini-length hem, beaded fringe trim
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000375
Category Name: Casual Dresses
Price: $8.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Moves Fringe Bandage Maxi Dress
When the invite says dress to impress, this fringe bandage maxi dress understood the assignment. Designed in a sculpting bodycon fit with a strapless neckline and flowy maxi-length fringe, it hugs in all the right places and moves with you from dinner plans to the dance floor.
Fit & Features
- Structured bandage knit fabric, moderate stretch
- Strapless straight-across neckline
- Bodycon silhouette
- Mini-length hem
- Maxi-length fringe design
- Runs true to size
Style Number/Barcode: 05103-000865
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Refined High Neck Open Back Dress
Clean lines do all the talking in this sleek knit style. This midi dress combines a streamlined silhouette with an open-back design for a striking look from every angle. Perfect for summer cocktails, birthday dinners, and every RSVP that calls for something polished.
Fit & Features
- Ribbed knit texture with lining
- High neckline with adjustable shoulder straps
- Open back with O-ring hardware detail
- Body-skimming fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000367
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Brunch Then Cocktails Midi Dress
When the invite says casual chic, this is the dress you reach for first. The ribbed knit hugs in all the right places while the hardware detail and thigh-high slit give it that elevated, fashion-girl finish.
Fit & Features
- Rib knit stretchy fabric
- Strapless tube neckline with hardware insert
- Non-slip grip lining
- High front slit
- Form-hugging midi-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000369
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Resort State Of Mind Crochet Mini Dress
Consider this your out-of-office wardrobe in dress form. This crochet halter mini hugs in all the right places with a bodycon fit and lace-up back, making it perfect for sunset dinners, beach city strolls, and spontaneous weekend plans.
Fit & Features
- Crochet knit fabric, lined
- Halter neckline
- Bodycon mini-length silhouette
- Lace-up back detail
- Runs true to size
Style Number/Barcode: 06005-000370
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK, TEAL
Available Size: XS, S, M, L
Product Badge:- Sale