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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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: $42.90
Availability: Out of Stock
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Make It Sexy Off-The-Shoulder Mini Dress
Show off your curves in this sexy mini dress for weekend outings! The short dress features an off-the-shoulder neckline with a flirty bust keyhole tie, long sleeves with flared cuffs, side ruched seams to accentuate your figure, a bodycon silhouette, and a mini-length hem. Complete the look in lace-up stiletto heels and dare to be bold!
Fit & Features
- Off-the-shoulder neckline, bust keyhole tie
- Long sleeves with flared cuffs
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-6013
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK-2
Available Size: XS, S, M, L
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Effortlessly Chic Button Front Tunic
Create an effortlessly chic everyday look with this classic tunic. It features a collared neckline, a complete button-down front, long sleeves, and a cinched waist effect for a figure-flattering silhouette. Style this tunic with sleek hoops and clear mules.
Fit & Features
- Collared neckline
- Button-down front
- Long sleeves, single-button details
- Cinched waist effect
- Pleating detail
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1497
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
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Showstoppin' Staple Long Sleeve Maxi Dress
Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!
Fit & Features
- Hacci rib knit fabric, plenty of stretch
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5887
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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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: $26.90
Availability: In Stock
Available Color: HUNTER
Available Size: S
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So Fab Marble Print Mesh Mini Dress
Oh so fab, you'll turn heads in this alluring marble print mesh mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps to customize the fit, a mini-length hem with a cute lettuce-edge trim, and a bodycon silhouette that will hug your natural curves. The airy sheer mesh fabric includes a full knit lining and features an all-over marble print pattern. Style with lace-up heels.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Mini-length hem, lettuce-edge trim
- Bodycon silhouette
- Marble print
- Sheer mesh fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5272
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: XS, S, M, L
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Smooth Silhouette Ruched Bodycon Mini Dress
Sleek and smooth, this bodycon mini dress serves curves for days! Crafted from a soft double-lined knit fabric that fits like a glove, this dress features a square neckline adorned with adjustable spaghetti straps, side ruched seams to accentuate your figure along the bodycon silhouette, and a flattering mini-length hem. Complete the look with mules and a crop jacket.
Fit & Features
- Soft knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5683
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Scene Crew Neck Midi Dress
Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.
Fit & Features
- Crew neck, short sleeves
- Cutout waist, knot accent
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth cotton knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5765
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Cute And Casual Knit Hoodie Dress
This cute and casual knit hoodie dress is perfect for styling up for your weekend plans! It features a hoodie with a front drawstring, long fitted sleeves, and a mini-length, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch for ultra comfortable wear. Complete the look in this short dress with a plaid shacket and combat boots.
Fit & Features
- Hoodie, front drawstring
- Long fitted sleeves
- Mini-length hem
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5167
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: TAUPE-2
Available Size: S, M, L
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The One You Need Mini Dress
Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.
Fit & Features
- Sleeveless V-neckline
- Thin bungee straps
- Strapless bra recommended
- Mini-length bodycon silhouette
- Ribbed knit fabric
- Figure-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0500
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: TAN, BLACK
Available Size: XS, S, M, L, XL
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Perfectly Stylish Sleeveless Ribbed Knit Midi Dress
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- High front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1645
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: WHITE, BLACK, DARK, DENIM, RED, LIGHT, PINK, BROWN, BLUE-3, PEACH, MAUVE
Available Size: M, L, XS, S
Product Badge:- Sale
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Sunset Happy Hour Ruffled Skater Dress
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.
Fit & Features
- Sleeveless V-neckline
- Halter tie-back straps, open back
- Stretchy smocked high waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Twill fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-5531
Category Name: Casual Dresses
Price: $46.90
Availability: Out of Stock
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Covetable Charm Strapless Mini Skater Dress
From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.
Fit & Features
- Poplin stretchy fabric, sewn-in knit lining
- Back zipper and hook-eye closure
- Strapless square neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3082
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE, SAGE, DENIM
Available Size: XS, S, M, L
Product Badge:- Sale
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Cute And Casual Everyday Ribbed Knit Midi Dress
This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-4934
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
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What You Want Strappy Cutout Slit Midi Dress
This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!
Fit & Features
- Double-lined rib knit fabric, moderate stretch
- Spaghetti straps
- Square neckline
- Strappy cutout twist back
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5663
Category Name: Casual Dresses
Price: $26.00 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Gorgeous Arrival Rose Floral Chiffon Maxi Dress
Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.
Fit & Features
- Rose floral print
- Chiffon fabric lined with stretchy knit
- Padded bra cups, adjustable spaghetti straps
- Back zipper and hook-eye closure
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3128
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S
Product Badge:- Sale
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Cute Perfection Scoop Neck Bow Skater Dress
You'll look like cute perfection in this sleeveless skater dress at soirees! With adjustable spaghetti straps, a flattering scoop neckline, and three adorable bows with ruffle trim, this skater dress will have you feeling confident and stylish in its short-length hem. Complete the look in trendy sandals and a hair accessory.
Fit & Features
- Airy chiffon fabric, woven lining, no stretch
- Adjustable spaghetti straps
- Scoop neckline
- Back zipper and hook-eye closure
- Three bows with ruffle trim
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3453
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Right Impression V-Neck Floral Ruffle Skater Dress
A cutie like you will always make the right impression in this floral skater dress on dates or at brunch! Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.
Fit & Features
- Floral print, chiffon fabric with woven lining, no stretch
- V-neckline, V-cut back with spaghetti strap tie
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-2894
Category Name: Casual Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS
Product Badge:- Sale
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Sweetest Look Ditsy Floral Chiffon Babydoll Dress
Create the sweetest look for your summer plans with this adorable babydoll dress! The airy sheer chiffon fabric is detailed with a ditsy floral print and includes a full-length lining for coverage. The short dress features a sleeveless scoop neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a ruffled tiered A-line silhouette with an effortless flowy fit. Style with sneakers for a cute and casual summer outfit.
Fit & Features
- Ditsy floral print
- Sheer chiffon fabric with stretchy knit lining
- Ruched scoop neckline
- Adjustable spaghetti straps
- Smocked back
- Ruffled tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5451
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: RUST
Available Size: S
Product Badge:- Sale
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Paradise Pick V-Neck Cutout Tropical Maxi Dress
Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline, keyhole
- Cutout back
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5692
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreaming Of Paradise Cowl Neck Tropical Midi Dress
Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric
- Adjustable spaghetti straps
- Cowl neckline
- Bodycon fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5613
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Sale
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Darling Delight Sleeveless Lace Trim Skater Dress
When the occasion calls for flair, this sleeveless skater dress delivers with darling delight! Perfect for bridal showers, rehearsal dinners, and graduations. Made from a smooth chiffon fabric, the lace trim straps and hem add a delicate touch. Featuring a square neckline and ruched bust, the flattering skater silhouette will have you twirling all day! Complete the look in block heels.
Fit & Features
- Smooth chiffon fabric, stretchy knit lining
- Square neckline, lace trim straps
- Back zipper and hook-eye closure
- Skater silhouette
- Lace trim short-length hem
- Runs true to size
Style Number/Barcode: 05101-3563
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L
Product Badge:- Sale
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Desirable Sultry Sweetheart Bow Bodycon Mini Dress
The heart wants what it wants and you need this bodycon mini dress! With adjustable spaghetti straps and a sweetheart neckline trimmed with delicate lace and a satin ribbon bow, this dress adds a touch of sweetness while flattering your curves in the bodycon fit. Complete the look in stiletto heels and a chic mini purse.
Fit & Features
- Woven fabric, minimal stretch
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Sweetheart neckline with lace and satin ribbon trim
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5813
Category Name: Casual Dresses
Price: $14.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, CHAMBRAY
Available Size: S, M
Product Badge:- Sale