Casual Dresses
Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, 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 outing, these casual dresses are built to move with your mood—and your calendar.
HomeCasual Dresses

Product Recommendations
STYLE SPOTLIGHT
Discover New Skater Dress Styles
Everyday Ease: Casual Dresses for Cool-Weather Plans
From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends.
Laid-Back & Versatile
Knit, ribbed, and sweater dresses bring comfort and style to crisp fall days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.
Chic from Day to Night
Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in burgundy or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.
Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.
What Makes a Dress Casual?
Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.
Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.
How Do I Style a Dress Casually?
Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.
For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!
-
Shape Of Me Backless Mini Dress
You'll fall in love with the shape of your curves in this body-hugging mini dress perfect for bachelorettes or going wine-tasting! It features a sleeveless V-neck, bungee spaghetti straps, and a backless design with a lower ruched seam to accentuate your assets on the bodycon silhouette. Complete the look in platform wedges.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Backless design, lower ruched seams
- Bodycon silhouette
- Mini-length hem
- Brushed double-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5026
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
That 70s Chick Retro Print Mini Dress
Inspired by the groovy era, you'll look like a cute chick in this retro mini dress perfect for parties! It features a sleeveless square neck, spaghetti straps, side ruched seams that hug your figure, a bodycon silhouette, and a geometric-retro print design. Complete the look with bold earrings.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Geometric-retro print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5005
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Feeling Playful In Floral Babydoll Dress
You'll be feeling playful in this floral babydoll dress perfect for bridal showers or dressy weekend brunches! It features a sleeveless square neck, adjustable spaghetti straps, an empire seam, and a flared short-length hem. The dress is designed with flower appliques on airy chiffon fabric with a woven lining. Complete the look in cute wedges.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Empire seam, babydoll silhouette
- Flared, short-length hem
- Flower appliques, chiffon fabric, woven lining
- Runs true to size
Style Number/Barcode: 05101-2470
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweet Spring Vibes Floral Skater Dress
This adorable floral skater dress will bring those sweet spring vibes to your look! It features a sweetheart neckline, short puff sleeves, a high waist, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight chiffon fabric features a dainty floral print pattern. Style with strappy sandals.
Fit & Features
- Sweetheart neckline, short puff sleeves, elastic cinched hems
- High waist seam, smocked back design
- Short skater skirt, ruffled hem
- Fit and flare silhouette
- Small floral print
- Chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2080
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Golden Hour Floral Ruffled Skater Dress
Snap a dreamy pic for golden hour in this floral skater dress and watch the likes come through! It features an off-the-shoulder, sweetheart neckline with ruffle trim, peasant long sleeves, a smocked bodice with a front adjustable drawstring, a cutout waist, and a flowy tiered ruffled short-length hem. Complete the look in chic clear strap mules.
Fit & Features
- Off-the-shoulder, sweetheart neck, ruffle trim
- Peasant long sleeves
- Smocked bodice, front adjustable drawstring
- Cutout waist, skater silhouette
- Tiered ruffle short hem
- Watercolor floral print, non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 05101-1987
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
La Fleur Floral Mesh Midi Dress
It's love at first sight in this floral midi dress perfect for day dates! It features a sleeveless square neck, spaghetti straps that lead to the lace-up, a bodycon silhouette, and an asymmetrical side slit cutout. The dress is composed of a floral print mesh fabric with a stretch knit lining. Complete the look in lace-up heels.
Fit & Features
- Sleeveless square neck
- Spaghetti straps, lace-up back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Floral print mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4913
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Life Floral Chiffon Skater Dress
Live the sweet life twirling in this floral chiffon dress at birthday parties or baby showers! Featuring an adorable off-the-shoulder neckline with ruffle trim, short-sleeve cuffs, a bust keyhole cutout with a tie accent, and a short skater silhouette. The dress is composed of a dainty floral print chiffon fabric with a knit lining. Complete the look in simple platform heels.
Fit & Features
- Off-the-shoulder neckline, ruffle trim
- Short-sleeve cuffs, elasticized hems
- Keyhole bust with tie, back zipper, hook and eye closure
- Short skater silhouette
- Dainty floral print
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2038
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Effortless Romance V-Neck Midi Dress
Effortless and romantic, this sleeveless midi dress is a staple to have for every occasion! It features a V-neckline with a twisted bust, spaghetti straps, a form-hugging silhouette, and a sultry front slit. The mid-length dress is stretchy and double-lined. Complete the look in rhinestone mules.
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Twisted bust
- Form-hugging silhouette
- Front slit
- Midi-length hem
- Double-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5033
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Boss Babe Strapless Blazer Mini Dress
Giving boardroom meets bottle service in the chicest way. This strapless mini dress doubles as a statement piece that’s perfect for cocktail hour or styled up with sneakers for a cool-girl twist.
Fit & Features
- Woven fabric
- Strapless neckline, back zipper closure
- Faux button front accents
- Faux flap pocket accents
- Fitted silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000398
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: MOCHA
Available Size: XS, S, M, L
-
Strike Again Marble Print Mini Dress
Strike a stunning look every time you're in this knit mini dress at parties or nights out! It features a sleeveless one-shoulder neckline, dual spaghetti straps with a sultry cutout, a bodycon silhouette, and a trendy marble print on stretchy knit fabric. Complete the look in sandals.
Fit & Features
- Sleeveless one-shoulder neckline
- Dual spaghetti straps
- Cutout bust
- Bodycon silhouette
- Mini-length hem
- Marble print, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4932
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Made You Flirt Lace Skater Dress
Make your crush flirt with how cute you'll be looking in this lace eyelet short dress perfect for birthday brunches or parties! Featuring a sleeveless scoop neck, ruffled straps, a ruched bust, and a fit-and-flare skater silhouette. Style with a chic bracelet and heels to complete the look.
Fit & Features
- Sleeveless scoop neck, ruffled straps
- Ruched bust
- Fit and flare skater silhouette
- Short-length hem
- Lace eyelet fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2155
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Oopsy Daisy Print Knit Mini Dress
It's no mistake if this casual mini-dress makes its way into your cart! Perfect for weekend outings and day dates, this daisy print dress features a sleeveless V-neck, spaghetti straps, a center bust ruched seam for a cute scrunched look, and a bodycon silhouette. Complete the look in strappy platform sandals.
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Center bust ruched seam
- Bodycon silhouette
- Mini-length hem
- Ditsy daisy print
- Rib knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5041
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Timeless Love Rib Knit Maxi Dress
You'll adore this rib knit maxi dress time and time again! Create your capsule wardrobe with this perfect dress featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry side slit. Complete the look in a statement crop jacket, hoop earrings, and your go-to sneakers!
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Curve-hugging silhouette
- Side slit
- Maxi-length hem
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 05102-4916
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
For The Frill Ruffled Tie-Back Skater Dress
You'll totally be eyeing this skater dress for its frills! Have your twirl-worthy moment in this short dress featuring a square neck, short puff sleeves, a tie-back detail, and a flowy fit and flare silhouette with a tiered ruffle trim skirt. Complete the look with a trendy purse and mules for a baby shower or celebration!
Fit & Features
- Square neck, short puff sleeves
- Tie-back detail
- Flowy, fit and flare silhouette
- Tiered ruffle trim skirt
- Short-length hem
- Lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4851
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
A Flare To Remember Skater Dress
You'll be unforgettable in this short skater dress perfect for twirling into baby showers, brunches, and family parties! Featuring a sleeveless plunge v-neckline, spaghetti straps that cross and tie along the open back, and a fit-and-flare silhouette. The dress is composed of airy printed chiffon fabric with a smooth woven lining. Style with strappy mules and a clutch!
Fit & Features
- Sleeveless plunge v-neckline
- Spaghetti straps
- Open back, cross strap design, tie closure
- Fit and flare skater silhouette
- Short-length hem
- Airy printed chiffon fabric, smooth woven lining
- Runs true to size
Style Number/Barcode: 05102-4988
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Spring The Fun Sweater Midi Dress
Spring into this sweater midi dress for daytime outings! It features a sleeveless square neck, adjustable spaghetti straps, contrast trim along the bodice, and a bodycon silhouette. Style with trendy mules to complete the look!
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Contrast trim bodice
- Bodycon silhouette
- Midi-length hem
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1640
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
True Staple Short Skater Dress
A true staple for daytime soirees and celebrations! This short skater dress features a classic sleeveless square neck, adjustable spaghetti straps, a tie-front bust, flexible boning inserts along the bodice, and is composed of smooth woven fabric with a stretchy knit lining. Complete the look with a bracelet and heels.
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Tie-front bust, flexible boning inserts
- Skater silhouette
- Short-length hem
- Woven fabric stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2016
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Friendly Flirt Eyelet Mini Dress
Catch yourself a cutie-looking flirty in this eyelet mini dress featuring short puff sleeves, a sweetheart neck, a ruched bust with a tie front, a corset-seam bodice, and a bodycon silhouette. The dress is composed of stretchy eyelet lace fabric with a knit lining. Complete the look with a dainty choker and earrings set.
Fit & Features
- Short puff sleeves
- Sweetheart neck
- Ruched bust, tie front
- Corset-seam bodice
- Bodycon silhouette, mini-length hem
- Eyelet lace, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4978
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
In Plain Sight Smooth Knit Maxi Dress
This casual maxi dress will have you looking sultry on your off-duty days! This maxi dress is perfect for layering under your favorite sweaters or jackets for coffee runs and hangouts. It features a sleeveless square neckline, spaghetti straps, and a bodycon silhouette on stretchy, soft, and smooth modal knit fabric with a partial mesh lining. Complete the look in this long dress with an oversized jacket and sneakers.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Smooth knit modal fabric, partial mesh lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4897
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Whatever Rib Takes Cutout Mini Dress
Take on the day in style wearing this mini dress featuring a trendy, sleeveless, high neck, bodycon silhouette, and a cutout accent for a flash of skin. Complete the look in sunnies and sandals for the perf day date look.
Fit & Features
- Sleeveless, high neck
- Bodycon silhouette
- Cutout accent
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1270
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
One More Moment Sweater Dress
Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless square neck, spaghetti straps that lead to an open back with lace-up closure, a form-fitting silhouette, and a high side slit atop the midi-length hem. Complete the look with sandals and sunglasses.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Open back, lace-up closure
- Form-fitting silhouette
- Side slit, midi-length hem
- Sweater knit fabric, slightly sheer, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1688
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Easy Breezy In Floral Chiffon Dress
Easy, breezy, and beautiful! You'll adore this floral chiffon dress perfect for bridal showers or dressy spring parties. It features an off-the-shoulder, sweetheart neck, ruffled short-sleeve cuffs, a padded bust, a smocked back, and a flowy skater silhouette with a ruffled short hem. The dress is composed of an airy chiffon with a rose floral bouquet print and a stretchy knit lining. Complete the look in strappy sandals.
Fit & Features
- Off-the-shoulder, sweetheart neck, padded bust
- Ruffled short sleeve cuffs
- Smocked back, zipper nad hook-eye closure
- Flowy skater silhouette, ruffled short hem
- Rose floral bouquet print
- Airy chiffon, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2052
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cute Charm Ditsy Floral Skater Dress
Show off your cute charm in this adorable ditsy floral skater dress! It features a square neckline with a ruffled trim, a ruched bust with a tie-front detail, short puff sleeves, a fitted high waist seam, and a short flared-out skater skirt with a flowy silhouette. The lightweight woven fabric features a dainty ditsy floral print pattern. Style with espadrille sandals for a picnic date.
Fit & Features
- Square neckline, ruffled trim
- Ruched bust, tie-front detail
- Short puff sleeves, elastic cinched hems
- Back zipper, hook and eye closure
- High waist seam, short skater skirt, fit and flare silhouette
- Ditsy floral print, woven fabric, bust knit lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4854
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Lowkey Luxe V-Neck Mini Dress
She's flirty, she's fitted, and she moves like a dream. With a deep V-neckline and flowy hem, this mini dress is made for dinner and drinks at your fave chic spot!
Fit & Features
- Mesh-lined fabric
- Plunge V-neckline
- Wide shoulder straps
- Low-cut back
- Ruched fitted bodice
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000240
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: L