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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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: S, M, L, XS
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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, M, L
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: In Stock
Available Color: FUCHSIA
Available Size: XS, M
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Dress Code Destination Midi Dress
RSVP secured, outfit handled. This floral mesh midi dress brings sweeping ruffles, an open back, and a halter neckline together for the kind of entrance that gets compliments before you even reach your table.
Fit & Features
- Floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Open back
- Form-hugging fit
- Asymmetrical ruffled midi hem
- Runs true to size
Style Number/Barcode: 05102-000675
Category Name: Casual Dresses
Price: $24.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Prowlin' Tiger Mesh Mini Dress
Spotted: you owning every room you walk into. This tiger print mesh mini dress features a strapless neckline and breezy A-line fit—perfect for downtown plans, birthday dinners, and when your outfit needs to do the flirting.
Fit & Features
- Tiger print, sheer mesh fabric, lined
- Strapless neckline
- Flowy A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000962
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner At Eight Floral Maxi Dress
Some dresses get compliments. This one starts conversations. Featuring an elegant cowl neckline, an open-back halter design, and oversized floral artwork, this maxi dress was made for vacation dinners, wedding guest RSVPs, and every plan that deserves a dramatic entrance.
Fit & Features
- Tropical floral print, mesh fabric, knit lining
- Cowl halter neckline
- Open tie-back
- Side slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000678
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
Product Badge:- Sale
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Vacation Booked Tropical Floral Cutout Maxi Dress
This deserves a spot in your vacation photo dump. This tropical floral cutout maxi dress pairs a bodycon fit with a striking waist cutout, statement hardware detail, and a sweeping silhouette made for unforgettable entrances.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large tropical floral print
- Sleeveless sweetheart neckline, metal hardware accent
- Adjustable spaghetti straps, partially open back
- Front waist cutout
- Maxi-length hem with high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000673
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, L
Product Badge:- Sale
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Soft Cascade Ruffle A-Line Maxi Dress
Let the ruffles do the outfit planning. This A-line maxi dress pairs a plunging neckline and smocked empire waist with a cascading front detail for soft movement. Add bold jewelry and sleek sandals for an easy warm-weather look.
Fit & Features
- Gauze woven fabrication
- Plunging V-neckline with spaghetti straps
- Smocked empire waist
- Open back with tasseled tie detail
- Cascading front ruffle
- Flowy A-line maxi-length fit
- Runs true to size
Style Number/Barcode: 05102-000672
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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Vacay Ready Halter Mesh Romper
Booked the trip just to wear this. This tropical floral halter mesh romper drapes effortlessly, with a strappy open back and a cascading ruffle sash that moves with you.
Fit & Features
- Tropical floral print, mesh fabric, built-in shorts lining
- Halter cowl neck, tie straps
- Open strappy tie-back
- Tiered ruffled hem with flower inset, cascading ruffle sash
- Runs true to size
Style Number/Barcode: 06503-000269
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Curve High Slit Midi Tube Dress
Serving soft curves with a little edge—this one knows exactly what it’s doing. The midi tube dress hugs in all the right places with a high slit that makes every step feel intentional.
Fit & Features
- Ribbed cotton-blend knit fabric, high stretch
- Strapless sweetheart neckline, knot-front design
- High-cut side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000665
Category Name: Casual Dresses
Price: $19.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Vibe Paisley Print Bodycon Maxi Dress
The kind of dress that does all the talking the second you walk in. This paisley print bodycon maxi dress skims your shape with a soft, sculpting stretch—perfect for sultry nights out.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Paisley print
- Sleeveless square neckline
- Adjustable spaghetti straps
- High-cut side slit
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000687
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Serving Chic Halter Cutout Bodycon Midi Dress
Serving subtle drama with zero effort. This halter bodycon midi dress sculpts your shape with ribbed stretch and bold cutouts—made for nights when you want to feel chic and a little daring.
Fit & Features
- Hacci ribbed knit-lined fabric, high stretch
- Sleeveless crew neckline
- Halter tie-back straps, open back
- Waist cutouts leading to an open lower back
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000666
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, M, L
Product Badge:- Sale
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Gallery After Hours Cowl Neck Midi Dress
It’s giving art opening energy, but make it wearable. This artsy abstract print midi dress features a draped cowl neckline, delicate spaghetti straps, and a front slit on a form-hugging silhouette that feels equal parts effortless and elevated.
Fit & Features
- Abstract print, knit-lined stretch fabric
- Cowl neckline, Adjustable spaghetti straps
- Front slit
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000661
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Soft Curve Alert Rib Knit Midi Dress
Warning: compliments incoming. This rib knit midi dress features a sweetheart neckline, wide shoulder straps, and a cutout back that keeps things chic, while the form-hugging fit and side slit do all the subtle showing off for you.
Fit & Features
- Soft, stretch rib knit fabric
- Sweetheart neckline
- Wide shoulder straps
- Cutout back
- Side slit
- Form-hugging, midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000660
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Downtown Dinner Column Midi Dress
This midi dress keeps things polished from the front with a high boat neckline, then flips the script with a low back, sleek column fit, and just enough movement from the back slit. Perfect for pairing with heels.
Fit & Features
- Linen-like woven fabric, stretch knit lining
- High baot neckline
- Sleek spaghetti straps
- Low back, lower zipper and hook-eye closure
- Column midi-length silhouette
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-000648
Category Name: Casual Dresses
Price: $46.90
Availability: Out of Stock
Product Badge:- Sale
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Double Take Paisley Print Mesh Maxi Dress
Low back, high impact. This paisley print mesh maxi dress brings the drama with a curve-skimming fit, barely-there straps, and a draped back that keeps every exit memorable.
Fit & Features
- Paisley printed mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline, bar strap detail
- Spaghetti straps
- Open cross-back strappy design with tie closure
- Lower draped back
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000647
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free