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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Flirty Bloom Floral Ruffle Skater Dress
Serving soft-girl romance with a side of sass, this floral halter mini dress is made for twirls and double takes. Wear it when you want compliments on repeat.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, floral print
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Ruching, drop waist
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000297
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twist of Fate One Shoulder Mini Dress
Simply stunning and ready for date night or a bridal celebration, this sleek one-shoulder mini dress is made to hug in all the right places to flaunt your sultry curves!
Fit & Features
- Smooth woven stretch fabric
- One-shoulder neckline with twist strap
- Ruched bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000298
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Bloom Mesh Maxi Dress
Serving fierce meets floral—this mesh maxi dress is pure goddess energy. Perfect for a sunset dinner on vacay or a chic cocktail bar.
Fit & Features
- Leopard, floral printed mesh-lined fabric
- V-neckline, wide shoulder straps
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000296
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Plans Ruffle A-Line Romper
Your plans just found their outfit—this romper is all about fun with a flirty edge. The tie-back halter straps, ruffle overlay, and A-line fit make it a go-to for nights out or weekend parties.
Fit & Features
- Smooth knit fabric, high stretch
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Ruching, drop waist
- Mini-length tiered ruffle overlay, hidden fitted shorts
- Romper in size small is 29" shoulder to hem with a 9" front rise and a 1" inseam
- Runs true to size
Style Number/Barcode: 06503-000155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Nights Zebra Print Maxi Dress
Go full wild mode in this zebra mesh dress—plunging cowl neckline, open back with tie straps, and a daring thigh-high slit. The hardware trim at the waist adds just the right amount of edge for a dress that owns every room.
Fit & Features
- Zebra print, mesh fabric, stretch knit lining
- Plunge halter cowl neckline
- Open back with ties
- Hardware waist trim
- High front slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000292
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twirl Agenda Chiffon Mini Dress
Romantic with a little edge, this chiffon mini is made to move. The halter neckline, lace-up corset detailing, and tiered ruffles bring that flirty, fairytale energy—perfect for brunch to concerts, and daydreaming.
Fit & Features
- Chiffon fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Dual front lace-up plackets
- Corset-inspired fitted bodice
- Drop waist seam
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000293
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Nights Halter Slit Maxi Dress
Glam meets wild in this sultry halter maxi dress. With its curve-hugging fit, statement hardware, and bold slit, it’s made for spotlight entrances and after-dark drama.
Fit & Features
- Animal print, knit-lined fabric with stretch
- Halter neckline, hardware insert, spaghetti strap tie
- Bodice cutout with hardware insert
- High front slit
- Form-hugging silhouette, maxi hem
- Runs true to size
Style Number/Barcode: 05102-000294
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Own the Moment Tube Floral Slit Bodycon Maxi Dress
This strapless bodycon maxi dress brings major drama with a bold floral print and side thigh-high slit made to steal the spotlight at a beach brunch or on vacation!
Fit & Features
- Statement floral print, slinky knit stretchy fabric
- Tube neckline
- Side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000286
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace Me Up Denim Mini Dress
Denim but make it daring. This lace-up halter mini brings that effortlessly cool, slightly rebellious vibe—perfect for nights when you’re feeling bold and unstoppable.
Fit & Features
- Vintage-inspired denim fabric
- Halter plunge neckline
- Lace-up front bust design
- Stretchy smocked back panel
- Contouring seam detailing
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000288
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curve Flow Bodycon Midi Dress
Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks!
Fit & Features
- Soft modal-blend knit fabric, knit lining, moderate stretch
- Sleeveless mock neck
- Side ruched seams
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000287
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rodeo Rebel Faux Suede Mini Dress
Cowgirl, but make it hot. This faux suede mini dress brings western vibes with curve-hugging fit, embroidery details, and a button-front that’s strictly for show.
Fit & Features
- Western-embroidery, faux suede fabric, sewn-in knit lining
- Moderate stretch
- Strapless tube neckline
- Side zipper and hook-and-eye closure
- Faux front buttons
- Bodycon fit, mini hem
- Runs true to size
Style Number/Barcode: 05102-000148
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Agenda Long Sleeve Mini Dress
For the girl with a busy social calendar—this long sleeve mini dress is polished yet practical, featuring a sleek turtleneck, flattering knotted design, and a body-hugging fit that takes you from latte runs to casual dinners downtown.
Fit & Features
- Smooth knit-lined stretch fabric
- Fitted long sleeves
- Turtle neckline
- Front knotted design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000285
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Energy Ruffle Skater Dress
Playful yet sultry, this ruffle skater dress brings flirty energy with every move. The strappy open back and layered ruffled hem make it the perfect go-to for nights out or weekend plans.
Fit & Features
- Knit fabric
- Sleeveless plunging V-neckline, bar strap detail
- Tie-back halter spaghetti straps
- Open back, lower tie-back spaghetti straps
- Drop waist, tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000284
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easy Elegance A-Line Maxi Dress
Chic, minimal, and made for any moment. This strapless maxi dress keeps it effortless with a fitted bodice and flowy skirt that moves with you—perfect for everything from beach strolls to brunch dates.
Fit & Features
- Smooth knit stretch fabric
- Strapless tube neckline
- Fitted bodice
- Side pockets
- A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000281
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Instinct Tie Back Maxi Dress
Romantic with a wild streak. This halter maxi dress mixes abstract rose and animal prints with a lace-trim bust and open tie back—perfect for day or night out plans.
Fit & Features
- Abstract animal rose print, mesh-lined fabric, moderate stretch
- Halter plunge neckline, tie closure
- Lace bust
- Open tie back design
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000279
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Into Bloom Floral Maxi Dress
Romantic drama, unlocked—this floral maxi dress hugs in all the right places before flowing into a dreamy silhouette. With strappy back details and bold blooms, it’s perfect for autumn weddings, cocktail nights, or a dressy birthday event.
Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up strappy open back
- Curve-hugging silhouette
- Floor-length hem
- Runs true to size
Style Number/Barcode: 05101-000633
Category Name: Casual Dresses
Price: $7.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Allure Animal Print Cutout Maxi Dress
For the nights you want all eyes on you. This sultry animal print cutout maxi dress hugs every curve and serves bold, untamed allure to keep you as the main focus.
Fit & Features
- Sheer mesh fabric with mini-length brushed knit lining, high stretch
- Animal print
- Sleeveless plunging halter neckline
- Open back and sides, beaded accents, tie-back straps
- Maxi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000278
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Quiet Luxe Off-The-Shoulder Maxi Dress
Minimal effort, maximum impact. This off-the-shoulder maxi brings that sleek, sculpted vibe with a foldover neckline and curve-hugging silhouette that’s equal parts timeless and sultry.
Fit & Features
- Soft rib knit stretchy fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Center back slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000183
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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After Hours Pinstripe Lace Mini Dress
When the city lights come on, this dress takes over. The after-hours pinstripe lace mini serves sultry vibes with its corset fit, lace peekaboo, and flirty ruffle hem that’s made for late-night adventures.
Fit & Features
- Woven knit fabrication
- Pinstripe pattern
- Sleeveless sweetheart neckline
- Sheer lace panel front detail
- Tiered ruffled hemline
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05102-000276
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Can’t Stop Staring Bodycon Midi Dress
This sleek knit midi dress is giving heartbreaker energy! The ruched bodycon fit hugs in all the right places—perfect for date nights, girls’ nights, and spotlight-stealing entrances.
Fit & Features
- Smooth, stretchy knit fabric, knit lining
- Sleeveless V-neckline, padded bra cups
- Adjustable spaghetti straps
- Ruching
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000153
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seasons Favorite Off-The-Shoulder Midi Dress
A sweater dress, but elevated. With its foldover neckline and bodycon silhouette, this midi dress is a go-to for chic fall days or nights.
Fit & Features
- Rib knit fabric, moderate stretch
- Off-the-shoulder folded neckline, cinched seam
- Fitted long sleeves
- Bodycon fit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000162
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit to Stun Open Back Mini Dress
Keep your look playful and unexpected. This sweater mini dress keeps it sleek in the front, daring in the back. The cable knit keeps it cozy while the open back brings a hint of drama. perfect for fall slays.
Fit & Features
- Soft cable knit fabric with stretch
- Mock neckline
- Fitted long sleeves
- Open back cutout design
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000460
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: RAISIN
Available Size: XS, S, M, L
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Wrapped Up Cute Off-The-Shoulder Dress
Serving soft girl vibes with a flirty edge, this off-the-shoulder sweater dress hugs just right. Perfect for latte runs, weekend plans, or anytime you want cozy and cute in one move.
Fit & Features
- Soft cable knit fabric with stretch
- Off-the-shoulder folded neckline
- Fitted long sleeves
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 06005-000158
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: RAISIN, TAUPE, BROWN
Available Size: S, M, L
Product Badge:- Best Seller
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Sunkissed and Stunned Halter Striped Maxi Dress
This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.
Fit & Features
- Striped texture knit design, sheer fabric
- Halter plunge neckline, tie straps
- Open back with tie strap
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000137
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free