A dress that does the flirting for you. The cutout crochet shows just enough, while the shell and sequin details add that subtle shimmer that catches light—and attention—without trying. This is your out-all-day, glow-all-night kind of maxi dress.
Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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Coastal Crush Cutout Crochet Maxi Dress
Fit & Features
- Sheer crochet knit fabric, mini-length knit lining, moderate stretch
- Sleeveless ruched knit top, no-slip strip, wired V-neckline
- Tie-back halter spaghetti straps, eyelet trim, shell and sequin embellishments
- Partially open back
- Maxi-length hem, high-cut side slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000360
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Trouble Halter Romper
Playful yet bold. This halter plunge romper stuns with cascading ruffles and a flirty fit that’s ready for parties or date nights.
Fit & Features
- Smooth knit-lined stretchy fabric
- Plunge halter neckline, tie closure
- Side ruched seams
- Ruffled layer mini-length hem, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000192
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Attitude Cutout Mini Tube Dress
Sleek with a hint of attitude—this cutout tube dress leans into confidence without overdoing it. The smooth knit hugs effortlessly, while the cutout crisscross beading gives your waist that sculpted, stop-scrolling energy.
Fit & Features
- Smooth double-lined knit fabric, high stretch
- Strapless straight-across neckline
- Front waist cutout
- Asymmetric strappy design, beaded stone accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000359
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Yours Floral Romper
Steal the scene in this romantic flocked floral romper featuring a sultry halter neckline and flirty ruffled hem. The open strappy back adds just the right amount of drama for your weekend plans.
Fit & Features
- Flocked velvet floral pattern, mesh-lined fabric
- Plunge cowl halter neckline, tie closure
- Open dual tie-back design
- Form-hugging bodice
- Ruffled mini-length hem, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000193
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Crush Sherpa Trim Faux Leather Tube Dress
- Faux leather fabric with sewn-in knit lining, moderate stretch
- Faux sherpa trims
- Strapless straight-across neckline, no-slip strip
- Back zipper with hook-eye closure
- Dual belted accents at the waist
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000362
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Hour Off-The-Shoulder Mini Dress
This long sleeve off-the-shoulder mini dress hugs in all the right places for that effortless “oh, this old thing?” vibe. Perfect for brunch, dinner dates, or any casual night out plans.
Fit & Features
- Smooth knit-lined stretchy fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves with flare slit cuffs
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000363
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Whispers Ruffle Mini Dress
Bring the drama (and the movement). This strapless mesh mini features a sweetheart neckline with a sultry O-ring cutout, open tie-back design, and layered ruffle skirt made to turn heads on every dance floor.
Fit & Features
- Abstract print mesh-lined stretch fabric
- Strapless sweetheart neckline
- Hoop insert, padded bra cups
- Strappy open tie-back
- Ruched bodycon fit
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000367
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Prep School Princess Rhinestone Collar Shirt Dress
This polished poplin mini dress gets a glam upgrade with a gorge rhinestone-encrusted collar that instantly elevates your whole vibe. The corset-inspired seaming snatches your waist just right, while the flared skirt keeps things flirty. Whether you’re styling it with sheer tights and heels or chunky boots and a shoulder bag, this dress delivers classy-with-a-twist energy every single time.
Fit & Features
- Woven cotton-blend poplin fabric with structured hand
- Pointed collar adorned with rhinestone embellishments
- Long sleeves with buttoned cuffs
- Fitted corset-style waist with front pleating
- Mini-length button-up silhouette
- Runs true to size
Style Number/Barcode: 05102-000366
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wildly Fierce Leopard Floral Maxi Dress
Warning: this dress doesn’t do low profile. The leopard floral mesh print fabric and plunge halter neckline with bead inset sculpt a form-hugging maxi silhouette that’s made for vacations, birthday dinners, and any plan that deserves a little drama.
Fit & Features
- Floral, leopard print mesh-lined fabric
- Plunge halter neckline with tie and bead
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000365
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Worth The Wait Chain Detail Maxi Dress
The kind of dress that changes the whole plan. This abstract print maxi dress combines a plunging cowl neckline, draped chain detail, and an open-back silhouette for a look that's both art exhibit and dinner reservation.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless plunging cowl neckline, triple chain strap accents
- Tie-back halter straps, open back
- Maxi-length hem, high-cut back slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000370
Category Name: Casual Dresses
Price: $22.97 $48.90
On Sale: Yes
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L
Product Badge:- Sale
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Polished Curves Off-Shoulder Knit Midi Dress
This midi dress keeps it classy with a side of allure—the foldover neckline, sleek rib knit, and gold hardware detail turn a timeless silhouette into a subtle showstopper. It’s the kind of dress that makes minimal feel magnetic.
Fit & Features
- Rib knit fabric
- Foldover off-shoulder neckline with hardware accent
- Long fitted sleeves
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000232
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrapped in Charm Rib Knit Dress
Soft meets sultry in this rib knit mini dress made for showing a little shoulder. The foldover neckline, waist wrap belt, and ruffled hem bring that flirty-feminine vibe—perfect for when cozy still calls for a look.
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Wrap waist belt accent with hardware insert
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000371
Category Name: Casual Dresses
Price: $30.00 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Your Element Off-Shoulder Mesh Twist Midi Dress
This midi knows how to move—soft mesh, abstract swirls, and an off-shoulder twist that feels effortlessly seductive. The high side slit adds that perfect hint of drama, making every step a little more intentional.
Fit & Features
- Abstract printed mesh fabric, knit lining
- Off-shoulder neckline with twist detail
- Bodycon silhouette
- High side slit for ease of movement
- Runs true to size
Style Number/Barcode: 05102-000372
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Quietly Bold Lattice Side Midi Dress
This is the kind of dress that holds eye contact a second longer. Clean lines up front with a subtle lattice moment down the side make it feel polished, confident, and a little unexpected.
Fit & Features
- Ribbed knit fabric with stretch
- Square neckline
- Fitted long sleeves
- Side lattice cutout detailing
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000233
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Rhythm Halter Mini Dress
Made for movement and meant to turn heads. This abstract mesh halter mini dress features a soft cowl neckline, open back, and flirty tiered ruffle hem that dances with every step.
Fit & Features
- Abstract print, mesh-lined stretch fabric
- Cowl halter neckline with tie closure
- Open back
- Form-hugging fit
- Tiered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000373
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Intentions Zebra Velvet Maxi Dress
A little wild, a lot unforgettable. This burnout zebra velvet mesh maxi brings high-drama energy with its one-shoulder neckline, side cutout, and ruched bungee drawstring that lets you play with the slit height. Equal parts sleek and scandalous—just how we like it.
Fit & Features
- Zebra burnout velvet pattern, mesh fabric, sewn-in mesh lining
- One-shoulder neckline, bungee spaghetti strap
- Strappy back, bodice side cutout
- High front slit and ruched drawstring bungee cord
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000757
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Babe Bow And Floral Print Skater Dress
Soft florals, sweet bows, and a neckline made to flatter—this one feels instantly charming. The V-shaped drop waist and flutter sleeves keep it light, feminine, and perfect for brunch plans, daytime dates, and photo ops.
Fit & Features
- Poplin woven fabric, delicate lace trim detailing
- Bow and floral print
- Flattering V-neckline
- Short flutter sleeves
- Button-down front, V-shaped drop waist
- Short skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000768
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Picture Perfect Floral Corset Skater Dress
Soft florals, a cinched corset, and a skirt made to twirl—this one’s pure heart-eyes. The structured bodice keeps everything snatched while the skater silhouette brings effortless movement for brunch dates, parties, and photo-ready plans.
Fit & Features
- Poplin cotton fabric with a structured feel, floral print, tulle and woven linings
- Square neckline with dainty ruffled trim, thin tank shoulder straps
- Corset-inspired bodice with lace-up front detail, boning inserts
- Back zipper closure
- Drop waist silhouette
- Flared skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000765
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Vibes Geometric Knit Halter Mini Dress
Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.
Fit & Features
- Sheer embroidered knit fabric, knit lining, high stretch
- Abstract geometric pattern, metallic woven threading
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000377
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: BLUE
Available Size: XS
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Luxe Moments Removable Faux Fur Mini Dress
Giving retro glam with a cozy twist, this ribbed mini dress brings major soft-lux vibes. The faux fur collar and cuffs add effortless drama, making it the perfect piece for chilly nights when you still want to look very put together.
Fit & Features
- Rib knit fabric
- Deep V neckline with a removable faux fur collar
- Long sleeves with removable faux fur cuffs
- Front button-down design for adjustable coverage
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000378
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Bold Mock Neck Mini Dress
Minimal from the front, major from the back. This mini dress offers a bold cutout back with hoop accents and a bodycon fit that turns heads and gives your rotation a trendy upgrade.
Fit & Features
- Ribbed knit fabric with stretch
- Mock neckline with fitted long sleeves
- Sleek bodycon silhouette through the bodice
- Open-back cutout detail with a detachable hoop chain accent
- Mini-length skirt with a front side slit
- Runs true to size
Style Number/Barcode: 06005-000261
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brunch Crush Eyelet Skater Dress
Caught feelings for this one instantly. This eyelet knit skater dress hugs through the bodice, then flares into the prettiest mini, made for brunch dates, grad pics, and those “just stepped out” kind of days.
Fit & Features
- Eyelet knit fabric with knit lining, moderate stretch
- Sleeveless square neckline
- Princess seams
- Adjustable spaghetti straps
- Mini-length hem
- Skater silhouette, godet detailing
- Runs true to size
Style Number/Barcode: 05102-000381
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wander Off Tie Back Skater Dress
This paisley skater dress flows effortlessly with a halter V-neckline and an open tie back that feels easy, breezy, and effortlessly styles with sandals for sun-soaked days.
Fit & Features
- Paisley print, airy woven fabric
- Halter V-neckline with tie straps
- Open tie-back design
- Flowy skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000380
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: NAVY
Available Size: L
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Daylight Darling Eyelet Dress
This dress feels like sunshine plans waiting to happen. A knit eyelet skater dress with a scoop neckline and tie-back detail that brings the flirty flair to every plan.
Fit & Features
- Eyelet knit fabric
- Scoop neckline
- Spaghetti straps
- Tie-back design
- Layered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000383
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free