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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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, 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
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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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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
Product Badge:- New Arrival
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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
Product Badge:- New Arrival
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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
Product Badge:- New Arrival
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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: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: CHARTREUSE
Available Size: XS, S, M, L
Product Badge:- Sale
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Sleek Move Mock Neck Ribbed Knit Mini Dress
This ribbed knit mini dress keeps the silhouette sleek from neckline to hem. The fitted shape and mock neckline create a clean, streamlined look, while the side slit adds just enough movement. Style it with knee-high boots or a cropped jacket for a sharp finish.
Fit & Features
- Ribbed knit fabric, high stretch
- Mock neckline
- Long fitted sleeves
- Side slit
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000470
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Prep Play Plaid Mesh Halter Ruffle Mini Dress
The plaid mesh gives this mini dress a fresh, flirty edge, while the ruched bodice adds extra texture through the waist. The halter neckline keeps the shape sleek up top, and the tiered ruffle skirt brings playful movement below. Style it with knee-high boots and simple gold jewelry for a look that feels cute, current, and a little cheeky.
Fit & Features
- Plaid mesh fabric with knit lining, high stretch
- Halter V-neckline
- Ruched bodice detailing
- Tiered ruffle hem
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000850
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Cocktails At Eight Off-Shoulder Midi Dress
Perfect for a bubbly-filled evening, this midi dress stands out with chic hardware details and a form-hugging silhouette. Pair with a shoulder bag and an updo.
Fit & Features
- Slinky lined knit fabric, moderate stretch
- Off-shoulder neckline, hardware insert
- Form-hugging silhouette
- Front faux wrap design with hardware
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001803
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Sleek Silhouette Butterfly Print Maxi Dress
Butterflies, but make it sleek. This high-stretch mesh maxi dress hugs the figure with a bodycon fit, while the abstract butterfly print and mock neckline keep the look artful, elevated, and ready for plans.
Fit & Features
- Mesh fabric, high stretch
- Abstract butterfly print
- Sleeveless mock neckline
- Tank shoulder straps
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000847
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Sweet Flirt Mesh Ruffle Hem Mini Dress
This one keeps the shape sleek and lets the ruffles do the flirting. Ruched mesh defines the silhouette while the sweetheart neckline and drop waist flow into a tiered hem. It’s an easy club pick when you want your look to feel feminine, fitted, and fun.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless sweetheart neckline
- Ruched bodice and skirt
- Drop waist silhouette
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05103-001291
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Side Glance Polka Dot One Shoulder Mini Dress
The polka dot revival gets a polished update through an asymmetric neckline and streamlined bodycon shape. A draped off-shoulder detail breaks up the print with an unexpected twist, keeping the mini dress feeling current and fashion-forward. Finish it with pointed pumps and metallic jewelry for a fresh take on the trend.
Fit & Features
- Asymmetrical one-shoulder neckline
- Draped off-shoulder detail
- Polka dot print, lined mesh fabric
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000845
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Dot About You Pin Dot Halter Ruffle Romper
Polka dots are having another little moment, and this romper keeps the trend feeling fresh. A halter neckline and blouson bodice flow into a ruched waist, while the layered ruffle overlay adds playful movement over hidden shorts. The open back keeps the look cute, current, and a little unexpected.
Fit & Features
- Polka dot printed mesh fabric with knit lining, high stretch
- Sleeveless high halter neckline, tie-back straps
- Open back
- Blouson bodice, ruched waist
- Layered ruffle mini-length overlay
- Built-in hidden shorts
- Runs true to size
Style Number/Barcode: 06503-000430
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
- Polka dot printed mesh fabric with knit lining, high stretch
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Waist Focus Sash Bodycon Midi Dress
The silhouette keeps everything clean, fitted, and defined. This square neck bodycon midi dress follows the figure with a streamlined shape, while the ruched waist and front sash detail draw focus through the middle. The result feels sleek, sculpted, and confidently put together.
Fit & Features
- Sleek knit fabric, full knit lining, high stretch
- Sleeveless square neckline
- Tank straps
- Ruched waist
- Front sash detail
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000842
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: NAVY, BROWN
Available Size: XS, S, M, L, XL
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Curve Shift Striped Knit Bell Sleeve Mini Dress
This bodycon mini dress keeps the silhouette sleek with a softer finish at the neckline. The fitted shape and off-shoulder fold-over detail create a clean line, while the long bell sleeves add movement through the arms. Style it with pointed heels or knee-high boots to keep the proportions sharp.
Fit & Features
- Striped knit fabric, high stretch
- Fold-over off-the-shoulder neckline
- Long bell sleeves
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000462
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Vamp Twist Strap Off Shoulder Maxi Dress
Let the details do the dressing. This off-the-shoulder maxi dress pairs twisted straps, ruched shaping, and a draped low back with a sleek, sculpted finish. Style it with stiletto heels and statement earrings for polished evening plans.
Fit & Features
- Smooth, slinky knit fabric with stretch
- Off-the-shoulder neckline with twisted straps
- Ruched detailing through the waist and hips
- Low draped back
- Curve-hugging silhouette
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-000840
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Glow Floral Beaded Halter A-Line Mini Dress
Delicate florals meet high-shine detail here. This embellished mesh mini dress features intricate beading and sequins, a halter V-neckline, and an open back that keeps the design visually balanced. The result is a standout piece with texture built into every angle.
Fit & Features
- Mesh fabric with knit lining, moderate stretch
- Floral beaded and sequin embellishment
- Sleeveless V-neckline
- Halter strap
- Open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-001630
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: GOLD
Available Size: XXS, XS, S
Product Badge:- Best Seller
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Playful Striped Bodycon Mini Dress
The season’s stripe revival was made for a packed summer calendar. A sleek mini silhouette and minimal straps give this bodycon dress an easy, trend-forward finish. Add sandals and a purse for brunch, weekend plans, or vacations!
Fit & Features
- Stretch knit fabric, striped print
- Scoop neckline
- Adjustable spaghetti straps
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000451
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Cut To Impress Rib Knit Mini Dress
Minimal from the front with a head-turning back. This rib knit mini dress hugs the figure with a mock neckline, halter silhouette, and open-back cutouts made for vacations, dinner dates, or weekend looks.
Fit & Features
- Rib knit sweater fabric
- High halter neckline
- Cutout back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000447
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Curve Cut Mock Neck Mini Dress
This dress makes getting ready easy. Style the open-back mini dress with metallic heels and statement hoops, keeping everything else streamlined so the dress stays front and center. Finish with a sleek purse and heels for date night.
Fit & Features
- Sweater rib knit fabric with stretch
- Sleeveless mock neckline
- Open back
- Side slit
- Bodycon fit with mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000448
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Easy Twirl Mock Neck Knit Skater Mini Dress
Consider this dress your shortcut to a cute fall outfit. The mock neckline and rib knit finish make the mini dress feel polished for layering, while the skater skirt keeps it playful. Add boots, a trench, and a shoulder bag for coffee dates, pumpkin patches, and crisp autumn days.
Fit & Features
- Rib knit fabrication
- Sleeveless mock neckline
- Skater silhouette
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000443
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: S, L
Product Badge:- Best Seller
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High Standard Mock Neck Bodycon Midi Dress
The sweater dress is back in the fall rotation for a reason. This bodycon midi dress combines a mock neckline, ribbed texture, and side slit for a streamlined look. Style it with boots and jacket for the perfect autumn style.
Fit & Features
- Sweater rib knit fabric, moderate stretch
- Sleeveless mock neckline
- Bodycon fit
- Front side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000444
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L