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.
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.
-
Chic Charm Puff Sleeve Floral Mini Dress
Keep it charming and chic in a floral mini dress that keeps you looking gorge! The mini dress features an elastic square neckline, short puff sleeves, a ditsy floral print, and a mini length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Square neckline
- Short puff sleeves
- Ditsy floral print
- Mini length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-0787
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Blooming Floral Knit Maxi Dress
Showcase your beauty as the best-dressed wedding guest in this blooming floral knit maxi dress! Designed with a gorgeous floral print design, it features a sleeveless V-neckline, spaghetti straps that lead to a bold open back with a lace-up strappy design, a thigh-high front slit to show off your heels, and a slim-fit silhouette. Complete your look with sleek hoop earrings.
Fit & Features
- Floral printed knit fabric
- V-neckline, spaghetti straps
- Open back, cross-back lace-up straps
- Fitted floor-length skirt
- High front slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05101-0851
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Floral Vibes Smocked Mini Dress
Channel those floral vibes with a smocked mini dress that nails those lowkey vibes just right! The dress features a sleeveless square neckline, spaghetti straps, a floral print, a mini-length silhouette, and a smocked body throughout. The dress offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Floral print
- Mini length silhouette with ruffled hem
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0802
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
So Fierce Ribbed Knit Mini Dress
Keep it fab and fierce in a mini dress that keeps your look on point! The ribbed mini dress features a plunging sweetheart neckline, bust seams at the cups, adjustable spaghetti straps, and composed of a form-hugging ribbed knit fabric. Complete your look with hoop earrings and wedge heels.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Bust seams at the cups
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0792
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Can't Live Without Glam Ruched Mini Dress
Channel a glam look with a mini dress that showcases your fab taste! The dress features a sleeveless V-neckline, spaghetti straps, a backless design, a ruched body, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Backless
- Spaghetti straps
- Ruched body
- Mini-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-2928
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Stripe It Down Ribbed Button Down Midi Dress
Keep it stunning in a striped dress that wows. Step out for brunch in this midi dress that features an off the shoulder neckline with a sweetheart bust, short sleeves, a button-down front, and narrow horizontal stripes. Complete your look with strappy mules and sleek hoops.
Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Short sleeves
- Button-down front
- Narrow horizontal stripes
- Midi length silhouette with center front slit
- Ribbed knit fabric, form-hugging fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0795
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Perfect Look Plaid Knit Mini Dress
Get the perfect look for date night in this adorable plaid knit mini dress! It features a square neckline and a mini length, curve-hugging silhouette. Pair this chic dress with heeled booties and sleek hoop earrings.
Fit & Features
- Spaghetti straps
- Square neck and back
- Short, form-hugging fit
- Allover plaid print
- Knit fabric
Style Number/Barcode: 05102-0801
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
For The Love of Florals Mini Dress
Show off your love of florals in this frilly and flirty mini dress! Throw on your favorite wedges and dainty pieces for a brunch ready look!
Fit & Features
- Sweetheart Neckline
- Sheer Chiffon Long Sleeves
- Smocked Bodice
- Ruched Drawstring
- Daisy Floral Print
- Smocked and Chiffon Fabric
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0845
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Fresh As A Daisy Mini Dress
Keep your look fresh as a daisy this season with a pretty floral mini that brings the flutters! Pair this must-have mini dress with a pair of strappy heels for a head-turning look!
Fit & Features
- Square Neckline
- Bungee Straps
- Embroidered Daisy Print
- Lined Mesh Fabric
- Mini Length Silhouette
- Form Hugging Fit
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0791
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Good Vibes Tie-Dye Mini Dress
Bring the good vibes to your summer style with this adorable tie-dye mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, front ruched detailing, and a mini-length, curve-hugging silhouette. Complete the look with clear heels.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Ruching
- Short, form-hugging fit
- Mesh fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-0784
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Center Of Attention Mini Dress
All eyes will be on you in this casual-chic mini dress. It features a wide sweetheart neckline, short sleeves, seam details that run down the center, ruching, and a mini-length, curve-hugging silhouette. Style this dress with clear heels and a trendy shoulder bag.
Fit & Features
- Wide sweetheart neckline
- Short sleeves
- Center seam details
- Ruching
- Short, form-hugging fit
- Ribbed knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0786
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bring The Heat Maxi Dress
Bring the heat to your next vacay in this tropical printed maxi dress! It features an off-the-shoulder neckline, a flowy overlay with short sleeves, a high waist, a floor-length silhouette with a relaxed fit, and a thigh-high side slit. The all-over tropical palm leaf print is perf for your summer getaway! Style this dress with strappy sandals.
Fit & Features
- Off-the-shoulder neckline
- Flowy overlay with short sleeves
- High waist
- Floor-length silhouette, relaxed fit, high side slit
- Knit fabric, tropical palm leaf print
- Runs true to size
Style Number/Barcode: 05102-0778
Category Name: Casual Dresses
Price: $22.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Denim and Lace Open Back Mini Dress
Give our denim dress a glam touch with a little lace. The mini dress features a plunging v-neckline with lace trim, adjustable spaghetti straps that offer support, and a bold open back with bar strap ties. Complete your head-turning look with cork heels.
Fit & Features
- Sleeveless v-neckline with lace trim
- Adjustable spaghetti straps
- Open back with bar strap ties
- Mini length hem with lace trim
- Denim fabric
- Form hugging fit
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0774
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Rose Darling Sweetheart Neck Mini Dress
Enchant in this gorg mini dress that will make hearts flutter! The dress features a sweet ditsy rose print, a sweetheart neckline, a tie-front at the bust, short sleeves, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Style dress with dainty heart charm necklaces and mules for the perfect brunch date with bae.
Fit & Features
- Sweetheart neckline
- Tie-front at the bust
- Short sleeves
- Ditsy floral print
- Mini-length silhouette, form-hugging fit
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0775
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Total Sweetheart Floral High Slit Maxi Dress
Show off your sweet side with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a floral print, and a maxi length silhouette accented with a high side slit. The dress is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Floral print
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 05102-0773
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Slay In Style Ribbed Scoop Neck Midi Dress
Slay in this midi dress that brings some major chic vibes! The dress features a scoop neckline, tank-straps, and a chic tie-waist belt to create an hourglass illusion. Complete your night-out look with a faux leather jacket.
Fit & Features
- Scoop neckline
- Tank-straps
- Tie-waist belt
- Ribbed sweater knit fabric
- Midi-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0929
Category Name: Casual Dresses
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Ribbed Knit Ruffled Ditsy Floral Mini Dress
Slay in a gorge ditsy floral mini dress. A ditsy floral dress is a staple piece to have for brunch or a day date with bae. This must-have features a sleeveless sweetheart neckline with a tie-front accent and ruffled trim with matching ruffled spaghetti straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. The dress is composed of ribbed knit fabric that offers a moderate stretch. Complete your floral look with cork wedges and dainty rings.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front bodice
- Ruffled spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0769
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
All About Floral Lace Skater Dress
Showcase your love for lace with a skater dress that says it all! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a sheer floral lace back, and a flirty and flowy skater silhouette. Complete the look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, sheer floral lace back
- Hidden side zipper and hook and eye closure
- Skater silhouette
- Lined chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0832
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Too Sweet Sweetheart Ditsy Floral Mini Dress
You'll look too sweet in a floral dress that brings the charm. This pretty date-night dress features a sweetheart neckline, a tie front accent, and a ditsy floral print. Complete your look with a light wash denim jacket and wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Tie front accent at the center of the bodice
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0767
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ruffle Detail Eyelet Off The Shoulder Mini Dress
Ruffle up your gorg look with this effortless eyelet detail mini dress! Pair with some gold hoops and strappy mules for an everyday style you'll love!
Fit & Features
- Off the shoulder square neckline
- Short ruffle sleeves
- Ruffle overlay
- Center ruffle detail
- High waist
- Short ruffle hem
- Eyelet detail woven fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0764
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Basic Lace-Up Denim Mini Dress
Keep it basic with a cute denim mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and door knocker earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up back
- Mini length silhouette
- Denim fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0765
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Trendy And True Eyelet Mini Dress
Keep true to your love of trendy finds in this mini dress! The dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeves, a ruched center, an eyelet design, and a mini-length silhouette. Complete look with clear mules.
Fit & Features
- Off the shoulder neckline, sweetheart bust
- Short puff sleeves
- Ruched center
- Eyelet pattern
- Mini length silhouette
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-0762
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Meant To Be Ruffled Mini Dress
You and this dress are totally meant to be! The dress features a sleeveless V-neckline, spaghetti straps, lace-up back, a mini-length silhouette with a faux-wrap overlay, and ruffles. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with platform wedges and a butterfly necklace.
Fit & Features
- Sleeveless V-neckline
- Lace-up back
- Mini length silhouette
- Faux-wrap overlay
- Ruffles
- Lined mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0758
Category Name: Casual Dresses
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Love At First Bloom Ditsy Floral Mini Dress
Fall headfirst for this floral dress that showcases your sweet side. It features adjustable spaghetti straps, a ruffled sweetheart neckline with a center cutout and tie-front, a stretchy smocked back, and a short, curve-hugging fit. Complete your look with strappy sandals and a cute handbag.
Fit & Features
- Adjustable spaghetti straps
- Ruffled sweetheart neckline
- Center cutout and tie-front
- Stretchy smocked back
- Mini-length, form-hugging fit
- Sheer chiffon fabric with a ditsy floral print, woven lining
- Runs true to size
Style Number/Barcode: 05102-0756
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale