Casual Dresses
Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.
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Everyday Casual Dresses That Are Essential For Fall
It's time to elevate your look with cozy and stylish casual dresses from Windsor. Whether you're planning a leaf-peeping trip, catching up with friends over a warm latte, or simply looking to refresh your fall closet, our selection of trendy casual dresses for women has you covered.
For fall 2024, embrace rich autumnal colors like deep burgundy, burnt orange, or olive green. These shades perfectly capture the cozy essence of the season. Opt for casual dresses made from comfortable fabrics like rib knit, jersey, or faux suede to keep you warm as the weather cools. If you prefer an effortlessly chic look, try a sweater dress. This versatile style is ideal for transitioning from a casual day out to a cozy evening gathering. Pair it with ankle boots, a wide-brim hat, and a faux leather jacket for an on-trend fall look.
Looking for a dress that effortlessly takes you from day to night? Consider our selection of casually chic sweater dresses. These styles are polished yet cozy, perfect for any occasion. Elevate your casual dress ensemble with a pair of knee-high boots and a statement scarf for a sophisticated fall outfit.
Long casual dresses are also a must-have for fall 2024. Opt for casual maxi dresses in smooth, contouring designs made from lightweight fabrics. Choose from earthy tones like taupe and chocolate brown or go for classic black for the most versatile look. Wear your long casual dress with a chunky cardigan, leather sneakers, and a crossbody bag for a flawless #OOTD.
Whether you're planning a holiday getaway or simply updating your wardrobe, a smart casual dress code is an essential addition. They're comfortable, versatile, and perfect for any occasion. Refresh your closet with elevated casual dresses from Windsor and stay on-trend this fall. Shop now online or in-store!
What Makes A Dress Casual?
Aside from special occasion dresses and gowns, dresses can be casual depending on how you style them. Fabrication and design can also innately make a dress casual so choose knits and cotton blends or ditsy florals or neutral tone prints, like a snake print dress, as everyday basics. Knit and sweater dresses, updated regularly here, are stylish choices for work or date night. Avoiding heels and heeled mules, and pairing sneakers and lug boots instead come in handy to make any dress look more laid back. Layering knits like cardigans, sweaters, or even classic jean jackets that are naturally casual over any dress is an easy way to instantly dress down the look. Casual dresses with drawstrings and tie or button fronts are details that can give those laid-back vibes too. Like with shoes, often it’s what you wear with the dress that “dresses down” your look so choose hair accessories, makeup, and jewelry accordingly.
How Do I Style A Dress Casually?
Style a dress casually by choosing to complement apparel and accessories that are naturally casual like jean jackets, t-shirts, scrunchies, dainty or basic jewelry, simple crossbody bags, and casual shoes like strappy sandals or combat boots. Take a ruched form-hugging mini dress and add on a simple lariat necklace and chunky sneakers for a cool and casual look. Layer on a denim jacket over a basic knit midi dress and pair it with slides for a casual-chic feel. For road trips or weekend getaways, maxi and midi dresses can be layered any time of year with graphic tees and sandals or cropped sweaters and combat boots to create that laid-back vibe. Windsor has the best-selling selection of women's casual dresses and accessories to pair them with for that must-have chill look. Need some help? Our in-store stylists are always ready to help you find your perfect outfit. Come shop with us!
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Flouncin' Around Strapless Ruffle Mini Dress
Show off your fun and flirty side in this strapless mini dress at parties and on dates! Featuring a figure-hugging bodycon fit, side ruched seams, and a playful ruffled mini-length hem, this dress is perfect for any occasion. Complete the look with block heels.
Fit & Features
- Double-lined smooth knit stretchy fabric
- Strapless neckline
- Bodycon fit
- Ruffled
- Runs true to size
Style Number/Barcode: 05102-5771
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Fab Trendsetter Leopard Print Drop Waist Mini Dress
Fab trendsetter will be your vibe in this leopard print mini dress featuring an off-the-shoulder neckline with short sleeves, a drop waist seam, and an asymmetric tiered mini-length hem with an A-line fit. Style with knee-high boots!
Fit & Features
- Leopard-printed brushed knit fabric, plenty of stretch
- Off-the-shoulder neckline, short sleeves
- Drop waist seam
- Asymmetric tiered mini-length hem
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5904
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Everyday Beauty Sleeveless A-Line Mini Dress
This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5631
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Trendy Element Turtleneck Long Sleeve Mini Dress
Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!
Fit & Features
- Double-lined ribbed knit fabric, moderate stretch
- Fitted long sleeves
- Folded turtleneck
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5245
Category Name: Casual Dresses
Price: $28.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Forever Sweet Long Sleeve Drop Waist Skater Dress
Fit & Features
- Stretchy smooth knit fabric
- Square neckline
- Long fitted sleeves
- Ruching
- Drop waist
- Mini-length tiered skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3745
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
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Cool Staple Ribbed Knit Long Sleeve Midi Dress
This ribbed knit midi dress is designed with a cotton-blend fabric with a cool mineral wash offering plenty of stretch. The dress features a scoop neckline, long fitted sleeves, and a midi-length bodycon silhouette to show off your curves.
Fit & Features
- Cotton-blend ribbed knit fabric, plenty of stretch
- Mineral wash
- Scoop neckline
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5829
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, S, M, L
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Flawless Puff Sleeve Corset Midi Dress
Fit & Features
- Lined woven fabric, dainty sheer lace trim, minimal stretch
- Sweetheart neckline, ruched bust, keyhole cutout, bow-front detail
- Corset bodice, bust underwire, flexible boning
- Short puff sleeves, elastic cinched hems
- Smocked lace-up back, hidden zipper with hook-eye closure
- V-shaped drop waist
- Midi-length A-line silhouette, front slit
- Runs true to size
Style Number/Barcode: 05101-3573
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
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So Fab Drop Waist Halter Skater Dress
Fit & Features
- Ribbed cotton-blend fabric, moderate stretch
- Mineral wash
- Sleeveless halter V-neckline
- Partially open back
- Drop waist
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5857
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: DENIM, CHARCOAL
Available Size: XS, S, M, L
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So Iconic Abstract Print Ruched Mini Dress
Step out like the icon you are in a mini dress that features a plunging cowl neckline with halter neck ties for a secure fit, an abstract floral print, and ruching throughout to enhance curves. Style with clear heels.
Fit & Features
- Fitted mesh fabrication, moderate stretch
- Cowl neckline
- Open back, halter neck ties
- Abstract floral print
- Mini length hem
- Ruching
- Runs true to size
Style Number/Barcode: 05102-5786
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: PURPLE
Available Size: XS, S, M, L
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Gorgeous One Shoulder Bodycon Mini Dress
Look like a gorgeous dream in this sleeveless mini dress for showers, brunch, or parties! The one shoulder neckline adds a chic look, while the side ruched seams enhance your curves. The bodycon fit hugs your figure in all the right places along the mini-length hem. Complete the look with statement earrings.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- One shoulder neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3478
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress
Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.
Fit & Features
- Floral tie-dye print, smooth knit fabric, moderate stretch
- Strapless neckline
- Lace-up back design
- Form-hugging fit
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3277
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: MAUVE
Available Size: XS, S, M, L
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Chicest Vibe Drop Waist Bubble Hem Mini Dress
Fit & Features
- Ribbed knit and woven fabrics, moderate stretch
- Mock neckline
- Tank shoulder straps
- Drop waist
- Mini-length pleated bubble hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5861
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Cute In The City V-Neck Knit Midi Dress
You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.
Fit & Features
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Bell long sleeves
- Front and back V-neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5888
Category Name: Casual Dresses
Price: $33.90
Availability: In Stock
Available Color: BLACK, BLACK-2
Available Size: XS, S, M, L, XL
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Sheer Exellence Mock Neck Bodycon Mesh Midi Dress
Experience sheer excellence in this stunning mesh midi dress perfect for dinners downtown or concerts. The sheer short sleeves and mock neckline add a touch of chic, while the bodycon silhouette flatters your figure. The sheer mesh fabric and smooth knit slip provide a luxurious feel, and adjustable spaghetti straps ensure a perfect fit. Complete the look with this midi dress in block heels and a hair clip for a fashion-forward style!
Fit & Features
- Sheer mesh fabric
- Includes a smooth knit slip, adjustable spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5540
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Essential Staple Ribbed Knit Midi Dress
This sleeveless ribbed knit midi dress features a classic high round neckline and a bodycon fit with a bold front slit for movement. Perfect for layering with a jacket and flat shoes.
Fit & Features- Stretchy ribbed knit fabric
- High round neckline
- Sleeveless
- Front slit
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2027
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: OLIVE
Available Size: S, M, L, XL, XS
- Stretchy ribbed knit fabric
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Island Vibes Tropical Print Asymmetric Midi Dress
Channel those island vibes on your summer vacay in this tropical print asymmetric midi dress! The stretchy slinky knit fabric is accented with an abstract tropical pattern, an iconic look for your getaway. The mid-length dress features a sleeveless cowl neckline with chic draped detailing, tie-back halter straps, an alluring open back, an asymmetric high-cut hem, and a bodycon silhouette to hug your gorgeous curves. Style with sleek hoops for a sunset happy hour.
Fit & Features
- Abstract tropical print
- Stretchy knit fabric, knit bust lining
- Cowl neckline, tie-back halter straps
- Open back
- Asymmetric hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5810
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Weekend Feeling Sleeveless Bubble Hem Mini Dress
A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.
Fit & Features
- Knit fabric, moderate stretch
- Crew neckline
- Form-hugging fit
- Drop waist seam, bubble mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5873
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: XS, S, M, L
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Picturesque Cutie Corset Lace-Up A-Line Midi Dress
The perfect A-line midi dress for a picturesque look at showers, birthdays, or graduation! With a sweetheart neckline and adjustable straps, this dress flatters your figure while offering a touch of sweetness. The corset-inspired bodice and lace-up back add a hint of edginess, while the A-line silhouette and midi-length hem make it perfect for any occasion. Complete the look with earrings and block heels.
Fit & Features
- Woven fabric lined with stretchy knit
- Sweetheart neckline, drawstring tie
- Adjustable straps
- Lace-up back
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3606
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L
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Swoon Over You Strapless Lace Mini Dress
This stunning strapless lace mini dress will make everyone swoon over your beauty at summer parties! Crafted with an airy sheer lace fabric with a knit lining for coverage, this mini-length dress is the charming style you need for the season. It features a strapless straight-across neckline with a dainty trim, a ruched seam to accentuate your curves leading to an adjustable drawstring and side slit, a ruffled hem for a flirty vibe, and a bodycon fit to flaunt your figure. Complete your look with hoop earrings and espadrille sandals.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Strapless straight neckline
- Ruched seam, adjustable drawstring
- Side slit
- Ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3405
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: WHITE, BLACK
Available Size: S, M, L, XS
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Love Of Details V-Neck Lace-Up Skater Dress
Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.
Fit & Features
- Lace fabric line with stretchy knit
- Adjustable spaghetti straps, V-neckline
- Back zipper and hook-eye closure
- Mesh lace-up bodice
- Asymmetrical ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3436
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Abstract Marble Sleeveless Mesh Midi Dress
Fit & Features
- Abstract marble printed sheer mesh fabric with brushed knit lining, plenty of stretch
- Sleeveless crew neckline
- Tank shoulder straps
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5869
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, S, M, L
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Delightful View Collared Scenic Waist Skater Dress
You'll be such a delightful view in this collared skater dress strolling the streets of Silicy or downtown! Featuring long sleeves with buttoned cuffs and a collared V-neckline, hidden front hook and eye fasteners provide a seamless look, and a scenic printed waist and short skater silhouette add a touch of charm. Complete the look in heels and a crossbody purse.
Fit & Features
- Gauze woven fabric with lining, no stretch
- Collared V-neckline
- Hidden front hook and eye fasteners
- Scenic printed waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5638
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Life's A Picnic Sweetheart Lace Gingham Mini Dress
Life's a picnic when you look oh-so-cute in this gingham mini dress at summer carnivals and day dates! The adjustable spaghetti straps provide a perfect fit while the lace trim sweetheart neckline adds adorable vibes. The high waist seam and slim fit create a flattering silhouette, while the lace trim mini-length hem adds a playful touch. Complete the look in platform sneakers.
Fit & Features
- Gingham print, cotton woven fabric, no stretch
- Adjustable spaghetti straps
- Lace trim sweetheart neckline
- Lace trim high waist seam
- Slim fit
- Lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5781
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: RED
Available Size: M, L
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Cutest Vibe Halter Drop Waist Skater Dress
Fit & Features
- Poplin woven fabric with knit lining, minimal stretch
- Deep V-neckline, dart seams at bust
- Tie-back halter straps, partially open back, lower back zipper with hook-eye closure
- V-shaped drop waist
- Pleated short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3516
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L