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!
-
Back To Basics Ribbed Knit Midi Dress
Every girl needs this basic ribbed knit midi dress in her line up! The dress features a classic crew neckline and short sleeves perfect for layering with a sweater or jacket and a form-hugging fit.
Fit & Features
- Ribbed knit fabric with brushed knit lining, plenty of stretch
- Crew neckline
- Short sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5603
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Confident Cutie Sleeveless V-Neck A-Line Mini Dress
Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!
Fit & Features
- Soft and stretchy rib knit fabric, full knit lining
- V-neckline
- Spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5651
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Stylish Persona Strapless A-Line Mini Dress
Turn on the charm in this strapless mini dress out on the town or at a party! The side ruched seam accentuates your curves while the A-line silhouette provides a flattering fit along the playful mini-length hem. Complete the look with heeled sandals.
Fit & Features
- Smooth knit fabric, moderate stretch
- Strapless neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-5642
Category Name: Casual Dresses
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Casual Chic Ruched Ribbed Knit Maxi Dress
Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.
Fit & Features
- Stretchy ribbed knit
- Boat neckline
- Tank shoulder straps, twist-back design
- Side ruching at the waist
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5834
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dream Twirl Tie Strap Pleated A-Line Mini Dress
Twirl all day in this pleated A-line mini dress at casual parties or outings! Featuring a flattering square neckline and delicate spaghetti strap ties, this A-line silhouette dress offers a flattering style. The hidden hook and eye fasteners provide a seamless look, while the pleated mini-length hem adds a flirty touch. Complete the look in platform shoes and earrings!
Fit & Features
- Stretch woven fabrication
- Spaghetti strap ties
- Square neckline
- Hidden front hook and eye fasteners
- A-line pleated silhouette
- Runs true to size
Style Number/Barcode: 05102-5737
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Charmed Success Lace Cold Shoulder A-Line Mini Dress
When you stroll into any event, you'll be a charming hit in this chiffon mini dress! The lace cold shoulder V-neckline and delicate spaghetti straps add a touch of elegance, while the satin bow adds a feminine and playful flair. With its A-line silhouette and mini-length hem, this dress is perfect for any occasion. Complete the look in stiletto heels and a clutch!
Fit & Features
- Chiffon fabric lined with stretchy knit
- Lace cold shoulder V-neckline
- Spaghetti straps, satin bow
- Back zipper and hook-eye closure
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3475
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Trendy Era Drop Waist A-Line Mini Dress
Enter your trendy era with this woven mini dress featuring a sleeveless square neckline and a halter strap accented with a buckle trim detail. The drop waist design leads to a short pleated A-line silhouette.
Fit & Features
- Woven fabric
- Square neckline
- Halter strap with buckle trim detail
- Partially open back, zipper closure
- Drop waist design
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5974
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cheerful Cutie Strapless Gingham Skater Dress
Spread your sunshine in this gingham skater dress for the sweetest look all summer! The strapless neckline, lace trim, and stretchy smocked waist create a flirty and comfortable look. The skater silhouette and ruffled mini-length hem with lace trim add a touch of cuteness to your look. Complete the look with a crossbody purse and sandals for any casual plans!
Fit & Features
- Gingham print, cotton fabric with woven lining
- Strapless lace trim neckline
- Stretchy smocked waist
- Skater silhouette
- Ruffled lace trim hem
- Runs true to size
Style Number/Barcode: 05102-5801
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
In The Mood Scoop Neck Lace A-Line Mini Dress
Get in the mood to romance your look with this lace A-line mini dress perfect for a dressy soiree! This fun and flirty lace A-line mini features a scoop neckline and adjustable spaghetti straps for a perfect fit while the mini-length hem adds a touch of flirty. Complete the look with the matching bolero.
Shop Matching Bolero: In The Mood Long Sleeve Lace Bolero
Fit & Features
- Lace fabric lined with stretchy knit
- Adjustable spaghetti straps
- Scoop neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3332
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wild For Style Strapless Zebra Print Midi Dress
Let this strapless midi dress tame your worries over having nothing to wear! It features a strapless neckline, a figure-flaunting bodycon silhouette, and a midi-length hem on zebra print knit fabric that gives you a wild style. Complete the look with earrings for any occasion!
Fit & Features
- Zebra print, knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5820
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Living A Dream Marble Off-The-Shoulder Midi Dress
This dreamy mesh midi dress is ready for you to take on any event! The stylish marble mesh fabric is sure to make a dramatic statement with its off-the-shoulder neckline, ruched fitted sheer long sleeves, flattering side ruched seams, and bodycon silhouette. Complete the look in stiletto heels for a birthday dinner or date night!
Fit & Features
- Off-the-shoulder neckline
- Ruched fitted sheer long sleeves
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Marble print, mesh fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05102-5332
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweet Escape Lace-Up Tropical Midi Dress
Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.
Fit & Features
- Tropical print, lined knit fabric, plenty of stretch
- Square neckline
- Spaghetti straps
- Lace-up back
- Asymmetric high-cut hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5564
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
True Love In Floral V-Neck Corset Skater Dress
This sleeveless mini dress features a flattering V-neckline, adjustable spaghetti straps for a customizable fit, and a corset-inspired bodice. The skater silhouette and tiered ruffle hem gives this dress the perfect look with heels.
Fit & Features
- Floral print mesh fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Corset-inspired bodice
- Skater silhouette
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3520
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Unforgettable Cutie Bow A-Line Ponte Mini Dress
Bring an unforgettable cute vibe in this strapless ponte mini dress perfect for semi-formal events or brunch! Featuring a strapless neckline with a charming bow and contrast trim, this dress boasts an A-line silhouette and a mini-length hem for a flirty and flattering look. Complete the look with a necklace.
Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless neckline, contrast trim and bow
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3636
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Good Looks Mock Neck Long Sleeve Knit Midi Dress
This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!
Fit & Features
- Soft and stretchy ribbed knit fabric
- Mock neckline
- Fitted long sleeves
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5221
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sassy Style Ruched Knit Halter Skater Dress
Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!
Fit & Features
- Stretchy smooth knit, top knit lining
- V-neckline, tie-back halter straps
- Partially open back
- Ruched seams at the waist
- Double-layered skater skirt
- Fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5832
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Trendy Girl Next Door Strapless Denim Mini Dress
Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight neckline, front no-slip strip
- Back zipper with hook and eye closure
- Faux chest pockets
- Cargo flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5524
Category Name: Casual Dresses
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Summer Vacay Lace-Up Tropical Maxi Dress
Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!
Fit & Features
- Tropical print, stretchy knit fabric
- Cowl neckline
- Spaghetti straps, lace up back
- Form-hugging fit
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-5743
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Destined For Love Lace-Up Short Skater Dress
You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.
Fit & Features
- Burnout pattern, mesh fabric, tulle and stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Lace-up, back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3319
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Preppy-Chic Belted And Pleated Skater Dress
This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.
Fit & Features
- Twill woven fabric, slight stretch
- Collared neckline, button-down front
- Cap sleeves
- Belted drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5915
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Twill woven fabric, slight stretch
-
Abstract Babe Ruched Mesh Midi Dress
Let your look do the talking in this mesh midi dress! With an eye-catching abstract print and adjustable spaghetti straps, this midi dress will show off your style while the bodycon fit and side-ruched seams enhance your curves. Complete the look in trendy mules for an art show downtown!
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruched seams
- Bodycon silhouette, midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5508
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Artsy Scene Mock Neck Abstract Mini Dress
Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.
Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5630
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bow Babe Strapless Pleated Ponte Romper
A strapless ponte romper features a form-hugging fit and a drop waist with an adorable ribbon bow and pleated short-length hem. Perfect for styling with a crop jacket and sandals.
Fit & Features
- Ponte knit fabric, slight stretch
- Strapless neckline
- Form-hugging fit
- Drop waist with ribbon bow trim
- Short pleated hem
- Runs true to size
Style Number/Barcode: 06503-1221
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Make Hearts Flutter Short Sleeve Cutout Maxi Dress
You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.
Fit & Features
- Gauze woven fabric, short knit stretchy lining
- Flutter short sleeves
- Plunge V-neckline and V-cut back
- Elasticized strappy waist with side cutouts
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5719
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free