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.
Now Trending
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.
-
Tropics Vibe Plunging Mini Dress
Transport to an island paradise with this vacay ready mini dress! It features a plunging wrap V neckline with a knot accent, long bell sleeves and asymmetrical mini length silhouette. The all over tropical print features palm leaves throughout. Dress is composed of an unlined lightweight woven fabric that offers a relaxed fit with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0427
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
All Over Ruffled Skater Dress
Get an adorable all over ruffled look in this pretty little skater dress.
Fits & Features
- Long Sleeves With Elastic Banded Ruffle Cuffs
- Deep V Neckline With Ruffle Trim
- Zipper & Hook And Eye Closure At Back
- Ruffle Tiered Detailing Along Flowy Skater Skirt
- Linen Composition
- No Stretch
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0419
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Basic Ribbed Knit Midi Dress
Dress up down or up with a basic midi this season girl! The dress features a mock neck, long sleeves and a midi length silhouette with a high side slit. Dress is composed of ribbed knit fabric that offers a form hugging fit with plenty of stretch. Perfect to pair with booties!
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0275
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Keeping It Fierce Snake Mini Dress
Keep it fierce in snake print! The bodycon features an off the shoulder neckline with ruffled trim, short sleeves, a sweetheart bust, a keyhole with tie front accent, a smocked back and a mini length silhouette. Dress features a snake print to perfectly matching with your favorite solid pieces. Garment is composed of a lined satin fabric that offers a relaxed fit with slight stretch.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0421
Category Name: Casual Dresses
Price: $9.97 $50.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sleeveless Leopard Chiffon Maxi Dress
Keep it sassy in spots with this pretty leopard maxi dress! It features a sleeveless bodice, a plunging wrap V neckline, adjustable spaghetti straps that lead to a strappy back design and a relaxed fit bodice that leads to a sweeping maxi length with a ruffled hem. Dress is composed of a semi sheer chiffon fabric that reveals a mini length knit lining. Garment offers a relaxed fit with a minimal stretch. Hidden back zipper closure included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0413
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Long Sleeve Knit Midi Dress
Keep it basic this season! The midi dress features a V neckline, fitted long sleeves vertical stripes and a midi length silhouette that rests slightly above the knee. Dress is composed of a lined knit fabric with a form hugging fit with a slight stretch. Zipper not included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0395
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Beautifully Buttoned Ribbed Sweater Dress
Button up in this casually chic sweater dress to impress this season! It features a wrap V-neckline, long sleeves, a multi-button down accent on the left seam and a mini length silhouette. Dress is composed of an unlined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included.Style Number/Barcode: 06005-0322
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Off Shoulder Sweater Dress
It's sweater time! We love a good sweater dress, just slip it on and you are ready! Designed with an off shoulder fold over neckline, long sleeves, and a form fitting silhouette. Dress is composed of a soft knit woven fabric that offers moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0068
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Own The Room Striped Knit Midi Tube Dress
Hot girl summer just got a little hotter. This striped midi tube dress hugs you in all the right places with a soft, textured knit that moves with you.
Fit & Features
- Striped textured cotton-blend knit fabric, lightweight knit lining
- Moderate stretch
- Strapless straight-across neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000019
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Leopard Cowl Neck Mini Dress
Keep your style untamed in this fierce leopard print mini dress! It features a sleeveless bodice, a cowl neck, adjustable spaghetti straps that leads to a square back and a mini length silhouette. Dress is composed of an unlined lightweight woven fabric with a satin-like sheen that offers a relaxed fit with a minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0326
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stylishly Destructed Tunic
This tunic is destructed with all the style! It features a crew neckline, long fitted sleeves, a short hem, and distressed slit detailing on the top and toward the hem. Tunic is composed of a cotten blend fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0276
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sultry Sweater Dress
Keep it classy in a sweater dress! This dress features a v neckline, and long sleeves that puff at the wrist with the help of a thick wristband. Bodice meets skirt high waist with a belt that ties at the side. Back of the garment has a tie detail below the neck.The hem of this dress hits mid thigh, and dress is composed of a knit material that offers a comfortable form fit with moderate stretch.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0076
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Forever Reckless Lace Up Tunic
You're a free spirit and you do what you want! This lace up tunic features short sleeves, a mid-thigh length, and a center script reading "Forever Reckless" in a bold contrasting print. The knit fabric offers moderate stretch and a relaxed fit.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06002-0224
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Hot In The Tropics Tropical Bodycon Mini Dress
Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination!
Fit & Features
- Tropical palm print, knit fabric, stretchy knit lining
- Scoop neckline
- Spagehtti straps
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000101
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Vintage Motors Slashed Mini Dress
Give your look some serious edge with this mini dress! It features a round neckline, long fitted sleeves and a mini length silhouette with slashed distressed detailing. The graphic at the center of the bodice features a motorcycle with wings and a graphic that reads: " Superior Motorcycle Vintage Garments." Mini dress is composed of a cotton-blend fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0242
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
What's Knot To Like Mini Dress
Take your look to the next level with this pretty mini dress! It features an off the shoulder neckline, fitted long sleeves, a cinching tie waist belt with loops and an asymmetrical mini length silhouette with a ruched detailing. Dress is composed of a lined crepe fabric that offers a curve hugging fit with a moderate stretch. Zipper not included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0336
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sophisticated Faux Suede Midi Dress
Keep it sophisticated in statement faux suede! The mini dress features a sleeveless bodice, a scoop neckline, spaghetti straps, vertical princess seams that create an hourglass illusion and a midi length silhouette with a side slit. The back features a sexy keyhole accent to show off more than a hint of skin! Dress is composed of a faux suede fabric that offers a form hugging fit with slight stretch.
Style Number/Barcode: 05101-0276
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sassy Snaps Ribbed Midi Dress
Keep it sassy as you snap into this must have! The dress features a crew neck, fitted long sleeves, a curve hugging midi length silhouette and a multi row snap button detail on the left side seam. Dress is composed of an unlined ribbed knit fabric that offers a moderate stretch.
Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0304
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Leopard Print Wrap Front Midi Dress
You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0396
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Plaid Knit Mini Dress
Pretty plaid is the way to go! This knit mini dress features a sleeveless bodice, spaghetti straps, a scoop neck, a square back, and a short, curve hugging fit. The dress offers plenty of stretch and includes a knit lining.Style Number/Barcode: 05102-0302
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Casual Cut Out Mini Dress
Cute and casual, this mini dress needs to be in your closet! It features an elastic banded off the shoulder square neckline, long fitted sleeves, a front waist cut out, and a short, curve hugging fit. Dress is composed of a ribbed knit fabric with plenty of stretch.
Hunter: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Rust: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0260
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
All Eyes on You Lace Low Back Midi Dress
Soft girl era, but make it spicy. With a sheer midi hem, sultry low back, and flirty side slit, this is the “accidentally iconic” dress for nights out, beach dates, or brunches.
Fit & Features
- Stretch lace knit fabric, partially lined
- V-neckline, spaghetti straps
- Low back cut
- Curve-hugging silhouette
- Sheer midi hem, side slit
- Runs true to size
Style Number/Barcode: 05102-000222
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Casual Knit Open Back Tunic
Keep it casual cutie with pretty knits! The tunic features a turtle neck, long sleeves with ribbed cuff, a partial open back and a short form hugging fit. Tunic is composed of knit fabric that offers a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0053
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Still Got Knit Mini Dress
Flaunt your love for knit with this casual mini dress! It features a turtle neck, long fitted sleeves and a curve hugging mini length silhouette that rests at the mid-thigh level. Dress is composed of a cable-knit fabric that offers a relaxed fit with a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0186
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance