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.
-
High Appeal Mock Neck Bodycon Mini Dress
A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!
Fit & Features
- Fitted long sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Cotton-blend knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5153
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Charming Duo Strapless Skater Mini Dress
A charming strapless skater dress you'll adore for brunch or family gatherings! Pair with the matching bolero for a complete look.
Fit & Features
- Soft rib knit stretchy fabric
- Strapless neckline, non-slip grip lining
- Skater silhouette
- Flair mini-length hem
- Runs true to size
Shop The Matching Bolero: Charming Duo Long Sleeve Bolero
Style Number/Barcode: 06005-2235
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Tea Time Corset Lace-Up Floral Skater Dress
It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!
Fit & Features
- Floral print, poplin woven lined lace trim fabric
- Square neckline, lace trim, underwire bust, wide shoulder straps
- Corset bodice, flexible boning, lace trim, lace-up back
- Drop waist seam
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3923
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Laced In Chic Lace-Up Skater Dress
Chic and charming, this lace skater dress boasts a flirty lace-up back that'll capture all the attention at parties!
Fit & Features
- Lace fabric, mesh lining, stretchy knit lining
- V-neckline
- Spaghetti straps
- Lace-up back
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3521
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Retro Vision Halter Striped Crochet Midi Dress
The perfect blend of modern and retro! This halter striped crochet midi dress can easily be styled with sandals for the day and heels for night.
Fit & Features
- Striped design, crochet fabric, short stretchy knit lining
- Halter neckline, spaghetti strap tie
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2264
Category Name: Casual Dresses
Price: $8.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Look Eyelet Knit Skater Dress
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.
Fit & Features
- Eyelet knit fabric with knit lining
- Sleeveless square neckline, underbust seam
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6001
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cool Breeze Cutout Striped Knit Mini Dress
As the temps rise so will your style in this striped knit mini dress with a flirty cutout back and bodycon fit perfect for layering with a denim jacket on cooler nights.
Fit & Features
- Striped pattern, knit fabric
- Scoop neckline
- Wide shoulder straps
- Cutout back
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2268
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Dream Of Me Corset Lace-Up Floral Midi Dress
Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.
Fit & Features
- Delicate floral print, woven fabric, tulle and woven linings
- V-neckline, adjustable spaghetti straps
- Hidden side zipper and hook-eye closure
- Corset bodice, flexible boning, lace-up back
- Voluminous A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3795
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Kissed By Blooms Corset Skater Floral Dress
Blossom so cute in this skater floral dress boasting a corset bodice that flaunts your femme figure and a trendy lace-up back for added allure!
Fit & Features
- Floral print, woven fabric, tulle and woven linings
- Sweetheart neckline
- Adjustable spaghetti straps, side zipper and hook-eye closure
- Lace-up smocked stretchy back
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3769
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Admired Cutie Floral A-Line Midi Dress
Catch every eye when you breeze by in this floral midi dress with flirty details like a corset-inspired bodice and a flowy A-line silhouette!
Fit & Features
- Ditsy floral print, woven fabric lined with tulle and stretchy knit
- Sweetheart neckline with bust tie
- Lace trim wide shoulder straps
- Back zipper and hook-eye closure, stretchy smocked back
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4053
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Ditsy floral print, woven fabric lined with tulle and stretchy knit
-
Beauty In The Detail Tie Back Floral Skater Dress
There's beauty in every detail on this floral skater dress from the flirty crisscross straps and tie-back design to the ruffled mini-length hem!
Fit & Features
- Floral print, woven fabric
- Square neckline
- Adjustable spaghetti straps
- Crisscross, tie-back design
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3992
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Forever Beauty Puff Sleeve Floral Chiffon Midi Dress
This breezy floral chiffon midi dress will forever be a beautiful style for bridal showers, parties, and brunches! The airy sheer chiffon fabric is accented with a dainty floral print for a soft feminine vibe and includes a knit lining for coverage. The mid-length dress features a ruched square neckline detailed with a keyhole cutout and tie-front design, adorable short puff sleeves with elastic cinched hems, fitted high waist seams, and a chic high front slit for added movement on the flowy A-line silhouette. Complete the look with heels.
Fit & Features
- Floral print
- Sheer chiffon fabric with stretchy knit lining
- Ruched square neckline, keyhole cutout with tie-front
- Short puff sleeves, back zipper with hook and eye closure
- High front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3033
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Prettiest Darling Puff Sleeve Floral Skater Dress
A pretty floral skater dress like this is everything this season! Designed with a dainty rose floral print, this mini dress features adorable puff sleeves and a tie bust that shapes the flattering a-line silhouette. Pair with boots.
Fit & Features
- Dainty rose print, woven fabric lined with stretchy knit
- Puff short sleeves
- Sweetheart neckline with bust tie
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3471
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Take Me There V-Neck Slit Bodycon Midi Dress
A perfectly flattering bodycon midi dress for any of your upcoming social plans!
Fit & Features
- Stretchy rib knit fabric
- V-neckline
- Spaghetti straps
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2286
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Easily Stunning Cutout Striped Midi Dress
This cutout striped midi dress was made for a laidback babe like you! With a bodycon fit and dual side slits for effortless allure, this dress is perfect for vacation or strolling the beach.
Fit & Features
- Striped print, stretchy knit fabric
- V-neckline with cutout
- Adjustable spaghetti straps
- Bodycon silhouette
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2290
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Chic Girl Short Sleeve Bodycon Slit Mini Dress
Enter a chic girl era in this sultry LBD designed in a flattering bodycon silhouette that flaunts your curves and a flirty front slit along the mini-length hem.
Fit & Features
- Smooth knit stretchy fabric
- Short sleeves
- Square neck
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5961
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Idea Of Bliss Corset Lace-Up Floral Skater Dress
Bold and pretty blooms dance across this dreamy floral skater dress perfect for sunshine dressing! The dress boasts an adorable corset bodice with lace trim and a back lace-up that turns heads while the voluminous skater silhouette has a romantic lace trim lining.
Fit & Features
- Floral print, woven fabric, multiple linings with lace trim
- Strapless neckline with bow, flexible boning
- Side zipper and hook-eye closure
- Corset bodice, lace trim, lace-up back
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3793
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Caught Your Eye Strapless Lace-Up Skater Dress
Catch every eye in this eyelet skater dress with a flirty lace-up bust and a flowy mini-length hem perfect for twirling at parties!
Fit & Features
- Eyelet cotton fabric with woven cotton lining
- Strapless neckline, lace-up bust, padded bra cups
- Skater silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4009
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Playful And Pretty Corset Lace-Up Midi Dress
Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.
Fit & Features
- Woven poplin lined fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable shoulder straps
- Lace-up back, side zipper and hook-eye closure
- A-line silhouette, front slit, side pockets
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3968
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Summer Vibe Polka Dot Satin Mini Dress
This polka dot satin mini dress will bring that sweet summer vibe featuring a dainty lace trim, halter V-neckline, and a short A-line silhouette. Style with sneakers for a casual look.
Fit & Features
- Satin woven fabric, sheer lace trim
- Polka dot print
- Sleeveless V-neckline
- Halter straps with tie-back design, open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000156
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Island Afterglow Knit Maxi Dress
Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.
Fit & Features
- Texture knit fabric, smooth knit lining
- Plunge V-neckline, hardware insert
- Long bell sleeves
- Cutout bodice, open back
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000155
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Weekend Chic Sleeveless Midi Dress
Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!
Fit & Features
- Woven fabric
- Boat neckline
- Low-cut back
- Drop waist seam
- Flowy silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000164
Category Name: Casual Dresses
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Compelling Romantic Off-The-Shoulder Pleated Maxi Dress
Make a toast to looking lovely in this off-the-shoulder pleated maxi dress as the bride-to-be or party guest! With a flowy silhouette and flattering drop waist seam, you'll look and feel so dreamy.
Fit & Features
- Smooth knit stretch fabric
- Folded off-the-shoulder neckline
- Drop waist seam
- Pleated flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3867
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bold Vibe Floral Print Strapless Bodycon Mini Dress
Look gorgeous at your getaway and show off a bold vibe in this knit mini dress designed with a large floral print to turn heads. It features a strapless straight-across neckline and a short bodycon silhouette to hug your curves.
Fit & Features
- Smooth knit fabric with knit lining, plenty of stretch
- Large floral print
- Strapless straight neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6047
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free