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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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: $32.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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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, no-slip strip
- 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
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 ribbed knit fabric with knit lining, high stretch
- 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:- Ships Free
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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: 05102-000696
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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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: Out of Stock
Product Badge:- Ships Free
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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
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Worth The Wait Midi Dress
Some outfits are good, this dress; was worth holding out for. This textured knit midi dress features a flattering bodycon fit, side slit, and statement open back that delivers from every angle.
Fit & Features
- Pointelle knit fabric, smooth knit lining
- Scoop neckline
- Adjustable spaghetti straps
- Dual twist open back detail
- Side slit
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000368
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: RED, OLIVE
Available Size: XS, S, M, L
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Midnight Magic Halter Mini Dress
A little sparkle and magic. Featuring a draped cowl neckline, open back halter design, and celestial-inspired sequin artwork, this sweater mini dress was made for cocktail parties, birthday dinners, and unforgettable entrances.
Fit & Features
- Sweater knit fabric
- Cowl halter neckline
- Open back with strap detail
- Sequin-embellished sun
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000360
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Escape Eyelet Mini Dress
This one belongs at sunset dinners, rooftop pics, and every RSVP you almost skipped. The eyelet mini dress hugs just right through the bodice with an easy flared fit that keeps it cute and comfortable all night.
Fit & Features
- Lightweight eyelet fabrication, knit lining
- Off-the-shoulder neckline
- Draped cold shoulder accents
- Ruched bodice
- A-line silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000691
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Obsessed Already Eyelet Knit A-Line Mini Dress
This one just does something to your confidence. The eyelet knit A-line mini dress hugs up top, flares just right, and feels like an easy yes for anything on your calendar.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Sleeveless sweetheart neckline, ruched bust
- Adjustable spaghetti straps
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000690
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Plans Striped Crochet Strapless Mini Dress
Sunny plans, cute outfit, and you’re already out the door. This striped crochet mini dress hugs just right up top with a strapless fit and flares into an easy A-line that’s made for brunch, beach days, and last-minute invites.
Fit & Features
- Striped crochet knit fabric with knit lining, moderate stretch
- Strapless straight-across neckline, no-slip strip
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000689
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girls Night Favorite Mini Dress
Step out ready to be complimented. This skater dress features an open back, a flirty mini-length silhouette - just add gloss, hoops, and somewhere to be.
Fit & Features
- Rib knit fabric
- Square halter neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000358
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
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Vacay Mode Tropical Floral Maxi Tube Dress
The suitcase practically packed itself. This tropical floral maxi tube dress combines a sleek bodycon fit with an oversized floral print for a look that feels effortless, elevated, and ready for every vacation itinerary.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large tropical floral print
- Strapless straight-across neckline
- High-cut back slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000688
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coast To Cocktails Halter Midi Dress
With textured crochet-inspired detailing, a halter neckline, and a body-hugging fit, this midi dress is ready for vacation dinners, bridal events, and every RSVP that calls for something elevated.
Fit & Features
- Texture crochet knit fabric, knit lining
- High halter neckline
- Form-hugging fit
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000352
Category Name: Casual Dresses
Price: $20.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: S
Product Badge:- Sale
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Minimal Muse Bodycon Midi Dress
Your new go-to dress when the vibe is effortlessly polished. This bodycon midi dress hugs in all the right places while the side slit offers effortless allure for brunch plans, vacations, or sunset cocktails.
Fit & Features
- Sweater knit fabric
- Scoop neckline
- Adjustable spaghetti straps
- Side slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000349
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Flare Polka Dot A-Line Mini Dress
Both flirty and impossible to ignore. This polka dot mini dress hugs in all the right places before flaring into an easy A-line fit that’s made for dinner dates, rooftop plans, and drinks with the girls.
Fit & Features
- Smooth knit fabric, high stretch
- Polka dot print
- Sleeveless deep V-neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000679
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Vacay Mood Tropical Floral Halter Skater Dress
Booked, busy, and dressed like it. This tropical floral halter skater dress hugs just enough up top, then flares into a playful, twirl-ready silhouette made for plans that don’t end early.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless plunging V-neckline, bar strap with beaded accents
- Halter tie-back straps
- Open back, lower tie-back spaghetti straps
- Tiered ruffled design, mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000674
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free