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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The 'It' Knit Sleeveless Maxi Dress
Take your trendsetting status to chic summer style with this sleeveless knit maxi dress perfect for styling over your swimsuit! It features a scoop neckline, tank shoulder straps, a form-hugging fit, and a flirty high-side slit on crochet-style knit fabric with a short stretchy lining. Complete the look in sunglasses and sandals!
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Form-hugging fit
- High side slit
- Maxi-length hem
- Crochet-style knit fabric, short stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5207
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Prints Satin Pleated Skater Dress
Play up your colorful side in this satin skater dress perfect for summer! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched tie-front bust, a stretchy smocked back, a flirty cutout, and a pleated short-length hem. The dress is designed with a multi-colored geometric print on smooth woven satin fabric. Complete the look in lace-up heels.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruched tie-front bust, stretchy smocked back
- Cutout accent, skater silhouette
- Pleated short-length hem
- Multi-colored geometric print
- Smooth woven satin fabric, no stretch, bust lining
- Runs true to size
Style Number/Barcode: 05102-5284
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Electric Love Chiffon Floral Maxi Dress
Look absolutely electric in this 70s-inspired chiffon maxi dress at parties and vacations! It features a sleeveless V-neckline, adjustable spaghetti straps that cross along the open back, an empire waist, and a flowy maxi-length silhouette on floral print chiffon fabric with a smooth woven lining. Complete the look with a sleek arm cuff bracelet and heels.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-open back
- Empire waist
- Flowy maxi-length silhouette
- Floral print
- Airy chiffon fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5264
Category Name: Casual Dresses
Price: $5.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Throwback Blues Denim Print Mini Dress
Let this printed denim mini dress cure your throwback blues! It features a sleeveless square neckline, tank shoulder straps, a bodycon silhouette, and a mini-length hem on smooth and stretchy knit fabric. Complete the look with classic hoop earrings.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Bodycon silhouette
- Mini-length hem
- Printed denim, smooth, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5229
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanna Getaway Chiffon Geometric Print Maxi Dress
'Tis the season for day trips, weekend getaways, or booking a flight out of town! This chiffon maxi dress will keep you stylish for it all. It features a sleeveless surplice V-neckline, spaghetti straps that crisscross along the open back, a tie-waist design, and a flowy silhouette with a flattering high front slit. Complete the look in statement sandals.
Fit & Features
- Sleeveless surplice V-neckline
- Spaghetti straps, crisscross open back
- Flowy silhouette, tie waist design
- High front slit, back zipper and hook-eye closure
- Maxi-length hem
- Geometric print, airy chiffon fabric, smooth woven lining
- Runs true to size
Style Number/Barcode: 05102-5265
Category Name: Casual Dresses
Price: $5.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Steal The Scene Halter Mini Dress
This is what "best dressed" looks like. With a ruched bodice and breezy A-line fit, this halter mini is perfect for date nights, vacays, or twirling at parties.
Fit & Features
- Slinky knit stretchy lined fabric
- Halter V-neckline, tie closure
- Ruched bodice
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000275
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love, Wear, Repeat Short Sleeve Maxi Dress
Love, wear, and repeat. You'll adore this maxi dress for all of your styling needs this season! It features short sleeves, a V-neckline, a form-hugging slim silhouette, and a floor-length hem on stretchy rib knit fabric. Complete the look in rhinestone hoop earrings for a dinner date.
Fit & Features
- Short sleeves
- V-neckline
- Form-hugging, slim silhouette
- Floor-length maxi hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5107
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tag You're Knit Bodycon Midi Dress
Tag you're it to rock this casually cute midi dress all over town! It features a sleeveless scoop neck, spaghetti straps, a flirty bust tie, and a figure-hugging bodycon silhouette with a side slit accent on stretchy rib knit fabric. Complete the look in sparkly teardrop earrings for an outdoor dinner party.
Fit & Features
- Sleeveless scoop neck
- Bust tie, spaghetti straps
- Bodycon silhouette
- Side slit accent
- Midi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5138
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Silhouette High Slit Maxi Dress
Show off your stunning silhouette in this curve-hugging high-slit maxi dress! It features a sleeveless square neckline, tank shoulder straps, a partially open back with a twist-back design and a lower back cutout, a maxi-length hem with a trendy thigh-high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch and has a sewn-in knit lining. Style with clear mules.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Partially open back, twist-back design, lower back cutout
- Maxi-length hem, thigh-high side slit
- Bodycon silhouette
- Ribbed knit fabric, sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4875
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Time To Unwind Tropical Slit Midi Dress
Take time to relax and unwind on your next vacation...in this stylish tropical midi dress! It features a sleeveless square neck, spaghetti straps, a bodycon fit, and a front slit accent on slinky knit-lined stretchy fabric. Complete the look in cute platform wedges.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Bodycon fit
- Front slit accent, midi-length hem
- Tropical palm leaf print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5177
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catching Flights O-Ring Halter Midi Dress
Catch flights not feelings! This halter midi dress is bringing those getaway vibes. It features a sleeveless halter neckline with a tank strap, an O-ring bust insert with a cutout accent and a form-hugging silhouette. Complete the look in cute flat sandals for a sunset cocktail hour!
Fit & Features
- Sleeveless halter neckline, tank strap
- O-ring bust insert, cutout accent
- Form-hugging silhouette
- Midi-length hem
- Stretchy rib knit fabric, knit lining
- Runs true to size
Style Number/Barcode: 05102-5002
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Art Show Marble Print Midi Dress
Look like a work of art in this marble print midi dress all over town! It features a sleeveless cowl neckline, spaghetti straps, a form-hugging fit with ruching down one side, and an asymmetrical side slit cutout on a smooth and stretchy knit fabric. Complete the look with hoop earrings.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Form-hugging fit, ruching down one side
- Asymmetrical side slit cutout
- Midi-length hem
- Marble print, smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4986
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Plans Rib Knit Bodycon Maxi Dress
Casual plans? Look amazing in this sleeveless maxi dress for everything on your social calendar! It features a square neckline, spaghetti straps, a bodycon silhouette, and a fitted long hem on stretchy rib knit fabric. Complete the look in cute flower earrings and sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi, fitted long-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5195
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slice Of Summer V-Neck Tank Maxi Dress
Break yourself off a slice of this summer-ready rib knit maxi dress you'll love taking on vacation or around town! It features a sleeveless plunge V-neckline, tank shoulder straps, a form-hugging slim silhouette, and a sexy high-side slit. Complete the look with statement earrings and sandals.
Fit & Features
- Sleeveless plunge V-neckline
- Tank shoulder straps
- Form-hugging, slim silhouette
- High side slit
- Maxi-length hem
- Soft and stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5080
Category Name: Casual Dresses
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dressing For Sunshine Eyelet Lace Mini Dress
The perfect eyelet lace mini dress for sunny days! It features adorable puff short sleeves, a sweetheart neckline, a front bust ruched drawstring, and a bodycon silhouette. The eyelet lace fabric includes a knit lining and offers moderate stretch. Complete the look in this mini dress with cute sandals.
Fit & Features
- Puff short sleeves
- Sweetheart neckline
- Front bust ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5118
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just Spotted Leopard Lace-Up Midi Dress
Just spotted, you in this effortlessly fierce leopard print midi dress! It features a sleeveless V-neckline with a twisted bust accent, spaghetti straps that lace up in the back, and a flattering A-line silhouette with a flowy hem. Complete the look with a sleek choker for lunch with friends!
Fit & Features
- Sleeveless V-neckline, twisted bust accent
- Spaghetti straps, lace-up back
- A-line silhouette
- Flowy midi-length hem
- Leopard print, breezy woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4976
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What A Girl Wants V-Neck Mini Dress
What a girl wants is this casual mini dress perfect for styling up or down! The dress features a sleeveless V-neckline, wide shoulder straps, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in stunning lace-up heels for a party.
Fit & Features
- Sleeveless V-neckline
- Wide shoulder straps
- Bodycon silhouette
- Mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5100
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easy Decision V-Neck Cutout Maxi Dress
A maxi dress you can style up or down? That's an easy decision! It features a sleeveless V-neckline, spaghetti straps, a knotted bust with cutout sides and back, and a hip-hugging slim silhouette with a sultry high-side slit on stretchy rib knit fabric. Complete the look in trendy sandals for a beach club or vacation!
Fit & Features
- Sleeveless V-neckline, knotted bust, spaghetti straps
- Side and back cutouts
- Hip-hugging, slim silhouette
- High side slit
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5094
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Spicy Scoop Neck Mini Dress
Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.
Fit & Features
- Sleeveless scoop neckline
- Dual spaghetti straps
- Strappy back design
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4804
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Energy Cutout Bodycon Mini Dress
You'll bring the party energy in this sexy cutout bodycon mini dress! It features a sleeveless one-shoulder neckline, a sultry asymmetric bust cutout creating two front tank straps, a mini-length hem, and a curve-hugging silhouette that will flaunt your gorgeous figure. The smooth nylon fabric offers plenty of stretch. Style with clear heels.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetric bust cutout
- Two front tank shoulder straps
- Mini-length hem
- Curve-hugging fit
- Nylon fabric, sewn-in lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5169
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Hour Goddess Cutout Maxi Dress
For when the invite says “yacht chic” and you’re ready to own the deck. The luxe cutout and gold hardware bring that high-glam energy, while the body-hugging fit keeps it sultry.
Fit & Features
- Smooth stretch fabric with lining
- Plunging halter V-neckline
- Statement gold hardware detail
- Front cutout design
- Form-hugging silhouette, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000411
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strappy And Stunning Rib Knit Midi Dress
Step out looking stunning in this rib knit midi dress for a casual beach day with friends or a date! It features a sleeveless V-neckline, spaghetti straps, a head-turning strappy open back, a bodycon silhouette, a side slit cut out, and a midi-length hem. Complete the look in trendy flat sandals and sunglasses!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Strappy open back
- Bodycon silhouette
- Side slit cut out
- Midi-length hem
- Rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5144
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Perfect Basic Knit Mini Dress
This casual knit mini dress is the perfect basic for creating cute everyday 'fits! It features a V-neckline, short fitted sleeves, a mini-length hem, and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with hoop earrings and strappy mules.
Fit & Features
- V-neckline
- Short fitted sleeves
- Mini-length hem
- Form-hugging fit
- Cotton-blend smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5050
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Infatuated Floral Satin Midi Dress
Spark everyones infatuation for you in this floral midi dress - a sultry style for wedding showers, graduations, and outdoor parties! The dress features a sleeveless cowl neckline, adjustable spaghetti straps, and a slim curve-hugging silhouette. Complete the look with a clutch and mules.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Slim, curve-hugging silhouette
- Midi-length hem
- Vintage rose floral print
- Silky smooth satin, no stretch
- Runs true to size
Style Number/Barcode: 05102-4942
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale