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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Invite Only Rhinestone Floral Dress
You weren’t planning on being the best dressed—but here we are. This strapless mini dress with a rhinestone floral detail brings just enough shine for every invite on your calendar.
Fit & Features
- Mesh-lined fabric
- Strapless tube neckline
- Side rhinestone floral embellishment
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000423
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island After Hours One Shoulder Maxi Dress
This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.
Fit & Features
- Tropical floral print knit fabric
- One-shoulder neckline
- Statement hardware strap detail
- Front slit with ruffle accent
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-000419
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Plans Chevron Crochet Maxi Dress
This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.
Fit & Features
- Chevron striped pattern
- Crochet knit lined fabric
- V-neck, spaghetti straps
- Lace-up back
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000418
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
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Undeniable Allure Halter Cutout Mini Dress
She doesn’t enter quietly—she arrives undeniable. A plunging halter cutout mini dress with bold metal hardware and a body-hugging fit that was made for rooftop nights, vacation dinners, and any plan that deserves extra.
Fit & Features
- Textured knit fabric, high stretch, sewn-in knit lining
- Sleeveless plunging V-neckline
- Dual circular metal hardware accents, waist cutouts
- Tie-back halter straps
- Open back, lower tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000417
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, L
Product Badge:- Sale
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Weekend Wandering Open Back Maxi Dress
Light, airy, and made for unhurried afternoons that turn into early evenings. This gauze maxi drapes effortlessly, skims the body just right, perfect for shower celebrations, vacation, or a brunch.
Fit & Features
- Soft gauze fabric with lightweight drape, knit lining
- V-neckline with cutout detail
- Spaghetti straps
- Open back with tie, zipper and hook-eye closure
- Fitted waist flowing into a relaxed maxi skirt
- Runs true to size
Style Number/Barcode: 05102-000416
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Desert After Dark Denim Mini Dress
Serving curves with a little edge. This denim halter mini dress features a plunging grommet V neckline and corset-inspired seams that sculpt your shape and keep all eyes exactly where you want them.
Fit & Features
- Denim fabric with color fade effect
- Halter neckline with grommet embellishments
- Back zipper and hook-eye closure
- Corset seam construction
- Open back with zipper closure
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000415
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Low Light Luxe Sequin Halter Mini Dress
Lights low, confidence high. This sequin halter mini is all about fluid shine and a plunging cowl neckline that moves with you—made for parties and nights out.
Fit & Features
- Sequin-embellished fabric, crochet fabric, knit lining
- Cowl halter neckline with hoop inserts
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000410
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 Intentions Flower Strapless Mini Dress
Soft details, confident energy. This strapless mini dress pairs a sweetheart neckline with a subtle cutout and floral accent for a look that feels romantic but never too precious.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Strapless sweetheart neckline, no-slip strip
- Front cutout with floral trim detail
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000412
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Mode Abstract Open Back Maxi Dress
This dreamy mesh maxi dress was made for golden hour plans, tropical cocktails, and dancing 'til dinner. Designed in an abstract print that brings the ocean and desert sky together, this halter dress features a draped cowl neckline, hardware straps, and open tie-back.
Fit & Features
- Abstract print, mesh-lined fabric
- Plunge cowl halter neckline with hardware
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000409
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Postcard Pretty Halter Cutout Maxi Dress
Booked the dinner, ordered the spritz, now you need the dress. This halter maxi dress brings the drama with a rose detail, front cutout, and tiered skirt that moves like you planned this all along.
Fit & Features
- Lightweight woven fabric with abstract print
- Halter neckline with rosette detail
- Front cutout with twist front bodice
- Smocked back for stretch
- Tiered ruffled maxi skirt
- Runs true to size
Style Number/Barcode: 05102-000411
Category Name: Casual Dresses
Price: $28.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Plans Tropical Floral Mini Tube Dress
A floral moment that knows it’s being noticed. This tropical floral mini tube dress hugs you in all the right places with a smooth, stretchy feel that’s made for warm nights, bold plans, and outfits that don’t blend in.
Fit & Features
- Smooth knit fabric, sewn-in lining
- High stretch for a body-hugging fit
- Large-scale tropical floral print
- Strapless straight-across neckline
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000413
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Frosted Charm Faux Fur Hem Mini Dress
This mini dress is the definition of winter glam—sleek brushed knit meets a plush faux fur hem that adds instant drama. It’s soft, stretchy, and serves that effortless luxe vibe from brunch to chic winter nights.
Fit & Features
- Brushed knit fabric with stretch
- Crew neckline
- Fitted long sleeves
- Bodycon silhouette
- Plush faux fur mini hem for a statement finish
- Runs true to size
Style Number/Barcode: 05102-000407
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Yours Off-Shoulder Mini Dress
A little flirty, a little free—this off-shoulder mini dress brings effortless charm with every move. The flowy sleeves and fitted hem keep it soft, flattering, and ready for any occasion.
Fit & Features
- Soft knit stretchy fabric
- Off-shoulder neckline
- Long sleeves
- Fitted mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000618
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bare It Boldly Open Back Mini Dress
Who knew soft could look this hot? This mini dress brings the drama with a low back cutout, halter neckline, and curve-hugging silhouette. Whether you're headed to dinner or turning heads at a party, this fit's got the bold factor locked.
Fit & Features
- Soft knit fabric with stretchy lining
- Scoop halter neckline with attached long sleeves
- Underwire bust design
- Open back cutout with adjustable halter tie
- Asymmetrical shark bite hem
- Runs true to size
Style Number/Barcode: 05102-000403
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Details Ponte Mini Dress
Structured, sleek, and a little daring. This ponte mini dress showcases chic details with its asymmetric mock neckline, knotted closures, and side slit detailing.
Fit & Features
- Smooth ponte knit fabric, minimal stretch
- Asymmetric mock neckline, short cap sleeves
- Knotted closures along the front
- Back zipper closure
- Form-hugging fit
- Side slit detail, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000406
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy And Captivating Bodycon Mini Dress
All eyes on you. This off-the-shoulder ribbed mini dress hugs every curve in soft, stretchy knit with a foldover neckline that adds just the right amount of flirt. The long sleeves balance the bodycon fit for a look that’s equal parts cozy and captivating.
Fit & Features
- Soft rib knit stretch fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000405
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Alluring Off-The-Shoulder Cutout Midi Dress
Dinner plans, last call, encore moment—this dress says yes to all of it. The off-the-shoulder neckline and front cutout keep things confident, elevated, and unforgettable.
Fit & Features
- Textured ribbed knit fabric, high stretch
- Off-the-shoulder neckline
- Long fitted sleeves
- Front cutout with hardware button details
- Bodycon silhouette
- Midi-length hem, high-cut side slit
- Runs true to size
Style Number/Barcode: 06005-000279
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Textured ribbed knit fabric, high stretch
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Esmerelda Denim Rhinestone Bodycon Mini Dress
Special Occasion
Built for that slow-motion entrance, this denim bodycon mini dress catches the light with every step thanks to its rhinestone-studded corset design. Luxe structure meets after-dark sparkle, giving you a look that feels polished, powerful, and impossible to forget.
Fit & Features
- Denim fabric with allover rhinestone embellishment
- Strapless neckline with structured corset bodice, flexible boning
- Back zipper and hook-eye closure
- Front pockets for convenience
- Bodycon mini silhouette
- Runs true to size
Where to Wear:
GNO, bachelorettes, date nights, birthdays, holiday parties
Style Number/Barcode: 05001-000634
Category Name: Casual Dresses
Price: $19.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep Them Curious Tie Back Mini Dress
This dress keeps it minimal from the front and magnetic from the back—the open cut and tie detail gives just enough drama while the rib knit smooths everything into place. It’s an easy yes for plans when simple feels the sexiest.
Fit & Features
- Rib knit fabric with subtle texture
- Boat neckline with long fitted sleeves and flared cuffs
- Bodycon silhouette through the bodice and skirt
- Open back design with wide band and tie-back closure
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000402
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Bloom Cowl Halter Maxi Dress
Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.
Fit & Features
- Tropical floral and leopard print
- Sheer mesh fabric, soft knit short lining
- Plunge cowl halter neckline
- Open back, lower ruched seam
- Front tropical floral hardware piece
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000401
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love At First Glance Long Sleeve Bodycon Mini Dress
This one knows exactly what it’s doing. A long sleeve bodycon mini dress with a scoop neckline and button cutout that hugs close, highlights just enough, and feels made for date nights and Valentine’s plans.
Fit & Features
- Textured stretch knit fabric
- Scoop neckline
- Fitted long sleeves
- Front cutout detail
- Decorative button accents
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-000276
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Focus Moment Ribbed Knit Midi Dress
Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat.
Fit & Features
- Soft rib knit fabric, sewn-in stretch lining
- Sweetheart neckline with twisted bust detail
- Spaghetti straps
- Fitted bodice through the waist
- Bodycon silhouette through the hips
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000397
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Snug Cable Knit Mini Dress
Cozy meets curve-hugging. This cable knit mini brings that soft, flirty energy with a foldover off-the-shoulder neckline and bell sleeves for extra charm. Perfect for date nights in or dressing up your coffee run fit.
Fit & Features
- Soft cable knit fabric, stretch knit lining
- Foldover off-the-shoulder neckline
- Long bell sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000395
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Can’t Resist Off-The-Shoulder Mini Dress
A little cozy, a little flirty—this rib knit mini dress does both. Designed with a foldover off-the-shoulder neckline, ruched sides, and a soft front drape that flatters every curve, it’s your go-to for coffee dates, casual dinners, or weekend chic plans.
Fit & Features
- Soft rib knit fabric lined with stretch knit
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Side ruched seams
- Front drape accent, bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000396
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free