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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Sweet And Chic Off-The-Shoulder A-Line Mini Dress
A little asymmetry never looked so chic. This off-the-shoulder mini dress features flattering ruching, a fitted drop waist, and a flirty A-line skirt for a playful twist on a polished silhouette.
Fit & Features
- Smooth knit fabric, high stretch
- Asymmetric off-the-shoulder neckline
- Ruched detailing, drop waist design
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000924
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Perfect Fit High Neck Bodycon Midi Dress
Consider this your new favorite way to look chic. This high-neck midi dress hugs your curves in stretchy ribbed knit fabric, bringing a refined, figure-flattering finish that pairs just as well with heels as it does with sneakers.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless high neckline
- Tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000921
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Sleek Intentions Off-Shoulder Bodycon Midi Dress
The off-the-shoulder trend is looking extra cute this season. A foldover neckline adds a playful touch to the fitted knit silhouette, while long sleeves keep the look sleek and balanced. It's giving sweet, polished style with just enough flirtiness.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Foldover off-shoulder neckline
- Long fitted sleeves
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000917
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: IVORY, DENIM
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Soft Angle Cowl Neck Bodycon Midi Dress
Chic, trendy, and made for a polished statement. This cowl neck bodycon midi dress elevates your weekly rotation with a curve-hugging design made for styling with crop jackets and heels or a dressy wrap and clutch for evenings out.
Fit & Features
- Cowl neckline
- Wide shoulder straps
- Fitted bodycon silhouette
- Subtle side ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-000907
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sleek State of Mind Mock Neck Midi Dress
Consider your everyday styling officially upgraded. This mock neck knit midi dress brings sleek sophistication with a flattering bodycon fit and stretchy ribbed texture that's ready for everything from coffee dates to dinner plans.
Fit & Features
- Hacci ribbed knit fabric, brushed knit lining, high stretch
- Sleeveless mock neckline
- Tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000903
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Cozy Allure Cable Knit Off-The-Shoulder Midi Dress
Who says cozy can't be a little sultry? This cable knit midi dress pairs a shoulder-baring fold-over neckline with a curve-hugging fit and a flirty front slit for a chic take on cold-weather dressing.
Fit & Features
- Cable knit fabric, moderate stretch
- Off-the-shoulder fold-over neckline
- Long fitted sleeves
- Midi-length hem, front slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 06005-000511
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Posh Glam Faux Fur Off-The-Shoulder Knit Midi Dress
A little faux fur, a whole lot of glam. The faux fur off-the-shoulder neckline brings the drama, while the high-stretch knit hugs your shape in a sleek midi dress silhouette.
Fit & Features
- Slinky knit fabric, high stretch
- Faux fur off-the-shoulder neckline
- Long fitted sleeves
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001811
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cozy Line Mock Neck Sweater Dress
Sweater dresses are back in the fall rotation with a sleeker point of view. The mock neckline, long sleeves, and fitted mini silhouette keep the shape clean while the ribbed trim adds just enough texture. Add knee-high boots for an easy seasonal finish.
Fit & Features
- Texture space-dye knit fabric
- Mock neckline
- Long sleeves
- Fitted silhouette
- Mini-length hem with slit accent
- Runs true to size
Style Number/Barcode: 06005-000507
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: DARK, MARSALA
Available Size: XS, S, M, L
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Cozy Crush Knit Off-The-Shoulder Mini Dress
Cold weather plans just got a flirty upgrade. This off-the-shoulder knit mini dress pairs a chic fold-over neckline with a curve-hugging bodycon fit and cozy ribbed texture for an effortlessly cute look styled with knee-high boots.
Fit & Features
- Hacci ribbed knit fabric, knit lining, high stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000892
Category Name: Casual Dresses
Price: $40.90
Availability: In Stock
Available Color: OATMEAL
Available Size: M, L
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Poised Long Sleeve Off Shoulder Mini Dress
This mini dress makes cold-weather styling feel a little cuter. The off-shoulder neckline and long sleeves balance each other perfectly, while the bodycon fit pairs easily with tall boots and a cropped jacket. Add a shoulder bag and simple jewelry for a polished seasonal look.
Fit & Features
- Brushed knit stretch knit fabric
- Foldover off-shoulder neckline
- Fitted long sleeves
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 05102-000890
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BEIGE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Bring The Drama Faux Fur Trim Knit Mini Dress
Consider your going-out look officially upgraded. This ribbed knit mini dress hugs the figure with plenty of stretch, while plush faux fur trim brings the drama to the neckline and sleeves.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Faux fur trim at the neckline and sleeve hems
- Long fitted sleeves
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000876
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Best Seller
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Preppy Attitude Plaid Knit Mock Neck Mini Dress
A little prep, a little attitude, and plenty of reasons to wear it on repeat. This plaid knit mini dress keeps things chic with a sleek mock neckline, curve-skimming bodycon fit, and a back keyhole cutout that's anything but predictable.
Fit & Features
- Plaid knit fabric
- Sleeveless mock neckline
- Tank shoulder straps
- Back keyhole cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000875
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Winter Muse Cable Knit Bodycon Dress
Your winter wardrobe has a new appreciation for the little details. This mock neck dress pairs trendy cable knit patterns with a bodycon fit and a cozy mock neckline for a fresh interpretation of traditional knitwear. Style with tights and boots for a dreamy winter look.
Fit & Features
- Soft cable knit sweater fabric
- Mock neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000496
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- New Arrival
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Contour Line Mock Neck Rib Knit Bodycon Midi Dress
The shape keeps everything sleek, simple, and close to the body. This mock neck bodycon midi dress follows the figure with a streamlined silhouette, while the ribbed knit texture adds subtle definition from top to hem. The result feels polished, sculpted, and easy to style.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Mock neckline
- Sleeveless cut
- Fitted bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000872
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: IVORY, BROWN
Available Size: XS, S, M, L
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Sweet Spot Lace Trim Polka Dot Mini Dress
The A-line shape gives this mini dress an easy, flattering flow with just enough swing through the skirt. A lace-trim neckline and polka dot print keep the look sweet, while the strappy back adds a more current finish. Style it with a pointed heel and a structured mini bag for a polished look.
Fit & Features
- Polka dot print, lined mesh fabric
- Lace-trim V-neckline
- Strappy open-back design
- A-line mini silhouette
- Lace-trim hem
- Runs true to size
Style Number/Barcode: 05102-000871
Category Name: Casual Dresses
Price: $48.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Sleek Crew Neck Long Sleeve Mini Dress
This mini dress keeps styling sleek with just the right amount of detail. The crew neckline and long sleeves create a clean base, while the draped waist detail adds shape and movement that pairs easily with heels and statement earrings. Finish it with a shoulder bag for a polished look.
Fit & Features
- Double-lined smooth knit fabric, high stretch
- Crew neckline
- Long sleeves
- Draped waist detail
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000868
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sleek Reveal Long Sleeve Cutout Midi Dress
This fitted midi bodycon makes a sleek base for dressed-up styling. The long sleeves and crew neckline keep the front streamlined, while ruching through the waist and hips and the open-back cutout add dimension from every angle. Pair it with sculptural heels and a statement bag for a polished finish.
Fit & Features
- Soft knit fabric
- Bodycon fit with midi length
- Crew neckline with long sleeves
- Ruched detailing through the waist and hips
- Open-back cutout
- Runs true to size
Style Number/Barcode: 05102-000865
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Chic Tie Front Long Sleeve Bodycon Mini Dress
This bodycon mini dress brings a sleek update to fall dressing. The long sleeves keep the silhouette season-ready, while the front tie defines the waist and hips for a trendy detail. Add boots and a crop jacket for a polished cool-weather look.
Fit & Features
- Sweater knit fabric with stretch
- Crew neckline
- Long sleeves
- Front waist tie detail
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000490
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Second Skin Long Sleeve Bodycon Mini Dress
This mini dress is all about a smooth, figure-following silhouette with a clean finish. The long sleeves add balance through the top while the short hem keeps the shape feeling modern. Add knee-high boots and a purse for an effortless day-or-night-out look.
Fit & Features
- Double-lined smooth knit stretchy fabric
- Fitted long sleeves
- Mock neckline
- Bodycon silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000861
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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After Hours Bloom Halter Maxi Dress
Dinner plans just got dangerously well dressed. This halter maxi dress hugs through the hips with sleek ruching, a statement floral accent, and a high slit made for entrances and exit shots.
Fit & Features
- Smooth stretch knit fabric
- Plunging V-neckline with halter straps
- Open back with adjustable tie closure
- Ruched hip with floral applique
- High side slit
- Maxi length silhouette
- Runs true to size
Style Number/Barcode: 05102-000822
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Curve Play Ruched Tie Back Mini Dress
The bodycon silhouette follows your curves with all-over ruching that creates a sleek, sculpted look. The plunging neckline and draped sleeves frame the top, while the tie-back detail adds definition. Style it with metallic heels and bold earrings for a confident dressed-up finish.
Fit & Features
- Smooth knit fabric, full knit lining, high stretch
- Plunging V-neckline
- Draped short sleeves
- All-over ruched detailing
- Tie-back design
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000859
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L
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Knit Shift Boat Neck Ribbed Sweater Mini Dress
The body-skimming mini dress silhouette balances a relaxed dolman top with a more defined shape through the skirt. The boat neckline keeps the upper half clean and open, while the ribbed texture adds subtle structure throughout. Style it with knee-high boots and bold earrings for a sleek cold-weather look.
Fit & Features
- Ribbed knit fabric with stretch
- Boat neckline
- Dolman long sleeves
- Defined waist
- Mini-length fitted silhouette
- Runs true to size
Style Number/Barcode: 06005-000473
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Sculpted Appeal Off-Shoulder Bodycon Midi Dress
Curves get the spotlight with a dress silhouette that knows how to work every angle. The asymmetric neckline and long sleeves balance a figure-hugging shape, while gathered ruching adds definition from waist to hem. The result is a sleek, sculpted look with just the right amount of drama.
Fit & Features
- Knit fabric, high stretch
- Asymmetric off-the-shoulder neckline
- Long fitted sleeves
- Ruched detailing along the sides
- Figure-hugging bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000853
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Polished Halter Bodycon Maxi Dress
A smooth, shine-kissed finish makes this one feel instantly dressed up. The curve-hugging shape, plunging neckline, and waist cutouts bring the drama for vacation dinners, cocktail parties, and every RSVP that needs a little extra.
Fit & Features
- Slinky knit fabric with stretch
- Halter neckline with plunging V front
- O-ring hardware at center waist
- Side and underbust cutout details
- Body-hugging maxi fit
- Runs true to size
Style Number/Barcode: 05102-000825
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Sale