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
As the fall season approaches, it's time to elevate your wardrobe 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 2024 collection, our selection of trendy casual dresses 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 styles made from lightweight knit fabrics. Choose from earthy tones like taupe and chocolate brown or go for classic black for the most versatile look. Style your long casual dress with a chunky knit cardigan, leather sneakers, and a crossbody bag for a flawless #OOTD.
Whether you're planning a fall getaway or simply updating your 2024 wardrobe, casual dresses are an essential addition. They're comfortable, versatile, and perfect for any occasion. Refresh your wardrobe with chic 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 style 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 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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Standout Staple Crew Neck Cutout Midi Dress
This midi dress may just become that special staple piece in your lineup! It features fitted long sleeves, a crew neck with a button-back closure and keyhole accent, a flattering bodycon silhouette and front slit, and a flirty cutout back design. Complete the look with statement earrings for a cocktail hour.
Fit & Features
- Fitted long sleeves
- Crew neck, back button closure, keyhole
- Bodycon silhouette, front slit
- Cutout back design
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5335
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Bold Allure Abstract Print Mesh Midi Dress
Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.
Fit & Features
- Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
- Lettuce edge hems
- Crew neckline
- Short cap sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5628
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Chic Muse Square Neck Bodycon Mini Dress
Show off your sleek chic style in this bodycon mini dress featuring a sleeveless square neckline, tank-like shoulder straps, and a short form-hugging silhouette. Style with stiletto heels for a rooftop bar!
Fit & Features
- Lined rayon knit fabric, plenty of stretch
- Square neckline
- Tank-like shoulder straps
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5970
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: BLACK, BURGUNDY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Flirty Babe Drop Waist Bubble Hem Skater Dress
You'll be a total flirty babe in this adorable short dress featuring a sleeveless square neckline with spaghetti straps, a V-shaped drop waist design, and a pleated skater silhouette with the cutest bubble hem. Style with hoop earrings and mules for date night!
Fit & Features
- Ribbed knit bodice, poplin woven skirt with knit lining, moderate stretch
- Square neckline
- Spaghetti straps
- V-shaped drop waist
- Short pleated skater silhouette with bubble hem
- Runs true to size
Style Number/Barcode: 05102-5907
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress
Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!
Fit & Features
- Jersey knit fabric with plenty of stretch
- Asymmetric off-shoulder neckline
- Long fitted sleeves
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5977
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: BLACK, BURGUNDY
Available Size: S, M, L
Product Badge:- New Arrival
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Bohemian Chic Lace Off-The-Shoulder Skater Dress
Channel that bohemian chic aesthetic in this airy sheer lace skater dress featuring an off-the-shoulder straight neckline with a fold-over design and sheer long fitted sleeves. The trendy V-shaped drop waist seam leads to a short uneven hem with a flowy skater silhouette.
Fit & Features
- Sheer lace fabric with partial knit lining, plenty of stretch
- Off-the-shoulder straight neckline with fold-over design
- Sheer long fitted sleeves
- V-shaped drop waist seam
- Short uneven hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3714
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Casual Chic Style Long Sleeve Ribbed Knit Midi Dress
The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.
Fit & Features
- Hacci ribbed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5920
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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
Product Badge:- New Arrival
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Chic Night Out Abstract Print Mesh Midi Dress
Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.
Fit & Features
- Sheer mesh fabric with brushed knit lining, plenty of stretch
- Abstract print
- Mock neckline
- Tank shoulder straps
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5929
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Chic Fall Vibe Ditsy Floral Corset Midi Dress
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit.
Fit & Features
- Ditsy floral-printed woven fabric
- Sweetheart neckline, ruched bust, tie-front detail
- Thin tank shoulder straps
- Corset-style bodice with piping, high waist seam
- High front slit
- Midi-length A-line fit
- Runs true to size
Style Number/Barcode: 05101-3706
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Casual Affair Long Sleeve Ruched Midi Dress
Fit & Features
- Smooth knit fabrication, moderate stretch
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3723
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cozy Knit Off-The-Shoulder A-Line Mini Dress
Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!
Fit & Features
- Soft ribbed knit fabric
- Off-the-shoulder straight neckline, fold-over design
- Long fitted sleeves
- Mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05102-5892
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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
Product Badge:- New Arrival
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So Adorable Drop Waist Bubble Hem Skater Dress
Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!
Fit & Features
- Double-lined brushed knit fabric, plenty of stretch
- Mock neckline, tank shoulder straps
- Ruching
- Drop waist seam
- Short skater silhouette
- Ruched bubble hem
- Runs true to size
Style Number/Barcode: 05102-5902
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Fresh Lines Sleeveless Pinstripe Mini Tube Dress
Fit & Features
- Woven knit fabrication
- Sleeveless square neckline
- Pinstripe pattern
- Faux front pockets
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5963
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sleek Essential Ribbed Knit High Slit Midi Dress
Accessorize a ribbed knit midi dress for the perfect fall outfit. The dress features a plunging V-neckline, long fitted sleeves, and a bold high slit. Complete your outfit with thigh-high boots.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- V-neckline
- Long fitted sleeves
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2079
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK, DARK, MARSALA
Available Size: XS, S, M, L
Product Badge: -
Blooming Beauty Floral Print Mesh Maxi Dress
Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels!
Fit & Features
- Mesh fabrication
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Floral print
- Bodycon-like fit
- Long maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3785
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L, XL
Product Badge: -
Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.
Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935
Category Name: Casual Dresses
Price: $9.97
Availability: Out of Stock
Product Badge:- Sale
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So Adored Sleeveless Bow Trim Crepe Mini Dress
Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!
Fit & Features
- Crepe fabric with knit lining, moderate stretch
- Sleeveless square neckline, dart seams
- Tank-like shoulder straps
- Bow accented trim under bust
- Back zipper closure
- Flared mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3840
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge: -
Social Butterfly Square Neck Floral Mini Dress
A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!
Fit & Features
- Woven fabric lined with stretchy knit
- Butterfly floral print
- Adjustable spaghetti straps
- Ribbon trim, front metal closures
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5623
Category Name: Casual Dresses
Price: $5.97
Availability: Out of Stock
Product Badge:- Sale
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Chic Staple Ribbed Knit Skater Dress
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over accent
- Long fitted sleeves
- Short-length hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06005-2070
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: OATMEAL, RAISIN
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Casual Dresses
Price: $5.97
Availability: Out of Stock
Product Badge:- Sale
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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
Product Badge: -
On The Down Low Denim Strapless Midi Dress
Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!
Fit & Features
- Strapless neckline
- Stretchy smocked back
- Button-down front closures
- Bodycon silhouette, midi-length hem
- Belt loop accents, three-pocket styling
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5283
Category Name: Casual Dresses
Price: $5.97
Availability: Out of Stock
Product Badge:- Sale