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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Lily Girl A-Line Mini Dress
A girl like you will love this floral mini dress for a sweet summer vibe! It features a sleeveless V-neck, spaghetti straps that lace up on the open-back design, a bodycon A-line silhouette, and a front slit accent. Complete the look in wedges.
Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Open-back with lace-up design
- Bodycon A-line silhouette
- Front slit accent
- Mini-length hem
- Floral print, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4618
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jetset Getaway Tropical Midi Dress
Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Open-back, cross-back strap design, tie closure
- Form-fitting silhouette
- Side ruched seam
- Asymmetrical midi-length hem, side slit
- Tropical floral print, stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 05102-4373
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Cruise Floral Midi Dress
You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back strap design
- Side ruching
- Midi-length, form-fitting silhouette, asymmetrical hem
- Tropical floral print
- Stretchy knit fabric, partial lining at the bust
- Runs true to size
Style Number/Barcode: 05102-4375
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mystic Swirls Square Neck Mini Dress
Create a sultry-mystic vibe for the night in this square neck dress featuring sleek spaghetti straps and a bodycon silhouette with backside ruching that accentuates every curve on the mesh-lined fabric. Complete the look in lucite mules.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ruched back detailing
- Marble swirl pattern
- Mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4453
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picnic Perfect Gingham Mini Dress
This gingham plaid mini dress is picnic-perfect! It features a sleeveless, sweetheart neck with adjustable bust tie and keyhole cutout, spaghetti straps, and a bodycon silhouette on stretchy knit-lined fabric. Complete the look in espadrille wedges for a day date.
Fit & Features
- Sleeveless, sweetheart neck, spaghetti straps
- Adjustable bust tie, keyhole cutout
- Bodycon silhouette
- Mini-length hem
- Gingham plaid print
- Stretchy knit-lined fabric
- Fits true to size
Style Number/Barcode: 05102-4694
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Day Ribbed Short Dress
Keep it casual in a cute short dress that is ready for brunch with the squad! The dress features a sleeveless V-neckline with ruching at the center, bungee spaghetti straps, and a short-length hem. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Ruching at center of bodice
- Bungee spaghetti straps
- Short length hem
- Lined ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1394
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sea Breeze Tropical Midi Dress
Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruching down one side
- Midi-length, asymmetrical hem, side slit
- Curve-hugging silhouette
- Palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4421
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Pretty As A Rose Crew Mini Dress
Look and feel pretty as a rose in this ditsy floral mini dress featuring a sleeveless crew neck, a bodycon silhouette, and adjustable ties at the hem that let you customize the length. Complete your look in a dainty bracelet for a backyard bbq.
Fit & Features
- Sleeveless, crew neck
- Ruching down the side seams
- Adjustable ties at the hem
- Bodycon silhouette, mini-length hem
- Ditsy floral print
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4713
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Occasion Ruched Side Mini Dress
Your next daytime occasion calls for this floral mini dress featuring a sleeveless, square neck, spaghetti straps, and side ruched seams that accentuate your curves on the soft-knit fabric. Complete the look with a cropped jacket.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Floral print
- Soft-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4606
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Florals Short Dress
Keep it pretty in a short dress that brings the charm! The dress features a pretty daisy print, a halter neck with neck ties, a square-neck smocked bodice, and a triple-row bar strap design at the back. The slim fit bodice leads to a fluttery A-line short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Halter neck with adjustable neck ties
- Square-neck smocked bodice
- Triple-row bar strap design
- Floral print
- A-line, short length hem
- Lined lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4401
Category Name: Casual Dresses
Price: $46.90
Availability: Out of Stock
Product Badge:- Sale
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Tropical Nights V-Neck Midi Dress
Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.
Fit & Features
- Sleeveless, v-neck
- Adjustable criss-cross spaghetti straps
- Bodycon silhouette
- Asymmetrical slit, side ruching
- Midi-length hem
- Tropical floral print, texture-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1455
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet Treat Puff Sleeve Mini Dress
This puff sleeve mini dress is the perfect sunny day sweet treat! It features a scoop neck, empire waist seam, bodycon silhouette, and a mini-length hem on jersey knit-lined fabric with a moderate stretch. Complete the look with a chic crossbody bag for a day out.
Fit & Features
- Puff sleeves
- Scoop neck
- Empire waist seam
- Bodycon silhouette
- Mini-length hem
- Jersey knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4677
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love Story Scoop Neck Mini Dress
It's a love story so baby, just say yes to this floral mini dress! It features a sleeveless, scoop neck, spaghetti straps, a bust tie-front detail, and a bodycon silhouette on rib-knit fabric. Complete the look in cute sandals for a lunch date.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Bust tie-front detail
- Bodycon silhouette
- Mini-length hem
- Ditsy floral pattern
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4402
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch Vibes Eyelet Skater Dress
Sweet and flirty, this eyelet knit skater dress is a must for weekend brunch! It features a sleeveless V-neckline with halter spaghetti straps, an open-back design, and a short skater skirt with a fit and flare silhouette. The lightweight knit fabric features an all-over floral eyelet pattern. Complete your look with a denim jacket and sandals.
Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie-back closure
- Open-back design
- Fit and flare silhouette
- Skater style-short skirt
- Floral eyelet knit fabric, lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4420
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daisy Darling Sleeveless Short Dress
Fall into a daisy daze with a short dress that brings all the feels! The dress features a sleeveless square neckline with lace trim, spaghetti straps, a pretty daisy print, and a short-length hem. The dress is composed of a brushed knit fabric with a form-hugging fit and moderate stretch. Complete the look in strappy mules.
Fit & Features
- Sleeveless square neckline, lace trim
- Spaghetti straps
- Daisy floral print
- Short length hem
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4479
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You'll Be Back Twist Bodycon Dress
You'll be back wearing this sultry bodycon dress on repeat! It features a sleeveless square neckline, sleek spaghetti straps, a mini-length hem, and an open back with dual twist accents that add sultry detail to your look. Style with a necklace and heels for a daytime party.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Open-back, dual twist accents
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4592
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shift In Seasons Floral Skater Dress
The sun rises with the shifting seasons and this flirty floral skater dress is ready to make an appearance! Featuring a sleeveless, square neckline, spaghetti straps, a smocked bodice, and a flowy, short skirt. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless, square neckline, spaghetti straps
- Smocked bodice
- Skater short silhouette
- Floral print
- Swiss dot chiffon, inner knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1507
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Girl Era Strapless Ponte Mini Dress
This strapless mini dress is giving timeless cute with a flirty edge. Just add hoops and your fave platform shoes.
Fit & Features
- Ponte fabric, stretch lining
- Strapless tube neckline
- A-Line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000271
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easy Decision Eyelet Tie-Back Dress
A sleek and easy piece to dress up or down? Decision made! Keep it trendy in this eyelet lace mini dress designed in a sleeveless scoop neckline, spaghetti straps, tie-back detail, and a bodycon silhouette. Complete the look in basic heels for an outdoor dinner party.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Tie-back detail
- Eyelet lace-lined fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4422
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Breeze Crochet Maxi Dress
Look and feel like a daydream in this boho maxi dress designed in a breezy, silhouette featuring a sleeveless, crochet lace v-neck bodice, spaghetti straps, and a sultry open-back with a tie closure that leads to the flowy long hem. Complete the look in strappy sandals.
Fit & Features
- Sleeveless, crochet lace v-neck bodice, spaghetti straps
- Open-back, tie closure
- Flowy maxi silhouette
- Long-length hem
- Partially lined woven fabric
- Fits true to size
Style Number/Barcode: 05102-4449
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Finest Floral Tie-Back Skater Dress
The florals on this skater dress are oh-so-fine! Create a cute spring look in this sleeveless, boat neckline, adjustable spaghetti straps, a flirty open-back with tie closure, and a ruffled skater silhouette. Complete the look in stud earrings for Easter brunch.
Fit & Features
- Sleeveless, boat neckline, adjustable spaghetti straps
- Open-back, tie closure
- Ruffled skater silhouette
- Short hem
- Floral chiffon-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4432
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Innocent Charm Eyelet V-Neck Dress
Innocently charming! Bring the flirtiness in this eyelet v-neck dress featuring a sleeveless ruffle trim bodice with tie-front closure, spaghetti straps, a cutout accent, and a form-fitting silhouette. Complete the look in a dainty choker necklace for a day date.
Fit & Features
- Sleeveless, v-neck, ruffle trim, spaghetti straps
- Tie-front closure
- Cutout accent
- Form-fitting silhouette
- Mini-length hem
- Eyelet knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4536
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Laced Up And Lovely Floral Corset Dress
Giving a fairytale with a flirty twist. This corset mini dress brings the drama with lace trim, a lace-up back, and a twirl-worthy skater skirt perfect for celebrations or garden soirees!
Fit & Features
- Floral print, woven fabric, woven lace trim lining
- Sweetheart lace trim neckline, bust tie, underwire bust
- Lace trim, adjustable shoulder straps
- Corset lace and pleated trim bodice, flexible boning
- Back zipper and hook-eye closure, lace-up back detail
- Drop waist seam, voluminous skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000067
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free