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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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
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Casual Chic Icon Long Sleeve Knit Midi Dress
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5895
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Whimsical Glam Bow and Lace Mini Dress
Fit & Features
- Lined rayon knit fabric with plenty of stretch
- Square neckline with lace trim inset and mini bow detail
- Cap sleeves
- Open back with lace-up bungee strap design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5839
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Back To Basics Ribbed Knit Midi Dress
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: $28.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, M, L
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Dainty-Chic Lace-Trim Woven Corset Skater Dress
This adorable lace-trim woven corset skater dress will bring a dainty-chic style to your party look. The sheer stretch woven fabric offers an airy, lightweight feel with a knit lining for coverage. The short dress features a square neckline with a scalloped lace trim and sheer lace cap sleeves for the prettiest detail. The ruched bust leads to a corset front with a lace-up design for a snatched look. The high waist flows out to a skater skirt with a fit and flare silhouette. Complete your outfit with rhinestone heels for that pop of sparkle.
Fit & Features
- Sheer stretch woven fabric with knit lining
- Square neckline with scalloped lace trim
- Sheer scalloped lace cap sleeves
- Ruched bust, corset bodice with lace-up front
- Back zipper, hook and eye closure
- High waist seam, skater skirt with fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3026
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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: $49.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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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: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
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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: $45.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS
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Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress
Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Cowl neckline
- Adjustable spaghetti straps
- Low back with criss-cross straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5645
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
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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: $34.90
Availability: In Stock
Available Color: NAVY
Available Size: S, M
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Love Impression Crew Neck Tie-Dye Bodycon Mini Dress
This tie-dye mini dress will have you falling head over heels! It features classic short sleeves and a crew neckline, a bodycon fit to flaunt your curves, and a mini-length hem. Complete the look with earrings and stiletto heels for any occasion!
Fit & Features
- Tie-dye print, mesh fabric, partial lining
- Crew neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5646
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
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Confident Moves Crew Neck Ruffled Mini Dress
Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.
Fit & Features
- Smooth double-lined knit fabric, moderate stretch
- Crew neck
- Bodycon fit
- Tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5792
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: M, L
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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: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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: $36.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: S, M, L
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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: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Pretty Lady Tie-Dye Cutout Dress
Channel a certain pop culture character from everyone's favorite movie! Go as a Pretty Lady this Halloween wearing this iconic mini dress featuring a sleeveless scoop neck, tank-style straps, a cutout bodice with an o-ring insert, and a tie-dye skirt. Complete your costume with chic thigh-high boots and hoop earrings.
Fit & Features
- Sleeveless scoop neck
- Tank-style straps
- Cutout bodice, o-ring insert
- Tie-dye mini skirt
- Bodycon silhouette
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4745
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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: $49.90
Availability: In Stock
Available Color: GRAY, BLACK
Available Size: S, M, L
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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: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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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: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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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: $32.90
Availability: Out of Stock
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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: $36.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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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
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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: $49.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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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
- 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: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
- Twill woven fabric