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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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: $33.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Sway With Me Halter V-Neck Paisley Skater Dress
Sway all day in this cute paisley skater dress perfect for summer parties and backyard BBQs! This dress features a halter V-neckline with spaghetti strap ties and a stretchy smocked bust for a flattering fit. The tie-back design adds a touch of playfulness, while the skater silhouette and ruffled hem will have you twirling all day! Complete the look in sandals and hoop earrings.
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline with spaghetti strap ties
- Stretchy smocked bust
- Tie back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5575
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M
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Lovely In Lace Ruffled Puff Sleeve Mini Dress
You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.
Fit & Features
- Sheer floral lace fabric with knit lining, minimal stretch
- Square neckline, ruffle trim
- Sheer short puff sleeves, ruffle trim
- Bust cutout, tie-front design
- Empire waist seam, hidden side zipper closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3338
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Picture Perfect V-Neck Smocked A-Line Midi Dress
You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.
Fit & Features
- Woven fabric lined with non-stretch woven
- Tie spaghetti straps
- V-neckline
- Stretchy smocked bodice
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3560
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: MINT
Available Size: S, M
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City Of Love V-Neck Ruffle Babydoll Dress
Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.
Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Side pockets
- Babydoll silhouette
- Ruffled tiered short-length hem
- Runs true to size
Style Number/Barcode: 05102-5423
Category Name: Casual Dresses
Price: $48.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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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
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Simple Staple Ribbed Knit Bodycon Mini Dress
Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1937
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: BLACK, TAUPE
Available Size: S, M, L, XS
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Coastal Dream Lace-Up Ruffled Maxi Dress
A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.
Fit & Features
- Woven fabric, short knit stretchy lining
- Scoop neckline with bust tie
- Adjustable spaghetti straps
- Lace-up back
- Flowy tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5565
Category Name: Casual Dresses
Price: $25.97 $56.90
On Sale: Yes
Availability: Out of Stock
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Perfect Match Sleeveless Striped Ribbed Knit Mini Dress
You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.
Fit & Features
- Striped pattern
- Ribbed knit fabric with moderate stretch
- Scoop neckline
- Tank shoulder straps
- Cutout back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1940
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: TAN
Available Size: S, M, L
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Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress
Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.
Fit & Features
- Polka dot print, satin fabric, no stretch
- Butterfly lace trim sweetheart neckline
- Button-down back and zipper hook-eye closures
- Cutout back accent
- Maxi length silhouette
- Runs true to size
Style Number/Barcode: 05101-3555
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, L
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Artsy Play Abstract Mock Neck Mini Dress
Play up your artsy side in this mesh mini dress totally giving those Y2K vibes! The mini dress features fitted long sleeves with split cuffs, a mock neckline, and a bodycon silhouette on mesh abstract printed fabric with a sheer mesh stretchy lining. Complete the look in chunky platform heels for a party!
Fit & Features
- Fitted long sleeves, split cuffs
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Abstract print on mesh fabric, sheer mesh stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5256
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress
Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.
Fit & Features
- Ribbed knit fabric with moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Twisted bust, cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5280
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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
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Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress
An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Spagehtti straps
- Square neckline
- Lace-up
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5689
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: M, L
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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
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Smooth Silhouette Mock Neck Mini Dress
Turn heads in this essential mini dress! Crafted with a double-lined smooth seamless knit fabric, the mini-length dress fits your body like a glove and features a mock neckline, fitted long sleeves, and a flattering bodycon silhouette. Make a statement and get compliments wherever you go styling this mini dress with combat boots and jacket.
Fit & Features
- Fitted long sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Double mesh lined smooth seamless knit fabric
- Buttery soft and stretchy
- Runs true to size
Style Number/Barcode: 05102-5384
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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
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In The Details Basic Ruched Midi Dress
The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Bodycon silhouette
- Midi-length hem
- Brushed soft knit fabric, lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5146
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
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Sensational City Girl Strapless Cargo Mini Dress
Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!
Fit & Features
- Cotton-blend woven fabric, minimal stretch
- Strapless straight neckline with belt loop detailing
- Front button closure
- Hidden front zipper closure
- Cargo flap pockets
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5503
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, XS
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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: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Weekend Vibes High Slit Striped Knit Maxi Dress
This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.
Fit & Features
- Striped ribbed knit fabric, short knit lining, moderate stretch
- Scoop neckline
- Spaghetti straps
- High side slits
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5778
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
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The Best Yet Sleeveless Crew Neck Slit Maxi Dress
The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!
Fit & Features
- Soft knit fabric, short lining, plenty of stretch
- Sleeveless crew neckline
- Tank straps
- Side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5588
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: S
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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: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Truly Chic High Slit Bodycon Midi Dress
Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Asymmetric midi-length hem, thigh-high side slit
- Bodycon silhouette
- Smooth knit fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5751
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L