Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Stylish Cutie Denim Lace Trim Mini Dress
This figure-flattering denim mini dress features delicate lace trim and a flirty ruffled hem that adds movement to your silhouette. The bodycon fit hugs your curves in all the right places, creating a stunning look.
Fit & Features
- Denim fabric, lace trim, minimal stretch
- Sweetheart neckline, added bra cups
- Wide shoulder straps
- Back zipper and hook-eye closure
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000104
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get It Girl Belted Skater Dress
Get a bold style in this belted skater dress! The fitted waist belt and seam details accentuate your silhouette, while the pleated skirt adds movement.
Fit & Features
- Twill stretch fabric, stretchy knit lining
- Strapless neckline with grommet trim
- Back zipper and hook-eye closure
- Seam detailing
- Belted waist
- Skater silhouette, pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000105
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hot In The Tropics Tropical Bodycon Mini Dress
Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination!
Fit & Features
- Tropical palm print, knit fabric, stretchy knit lining
- Scoop neckline
- Spagehtti straps
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000101
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Uniquely Darling Strapless Pleat Skater Denim Mini Dress
Darling and adorable, this denim mini dress brings flirtiness to any scene with a skater silhouette and pleated mini-length hem perfect for pairing with cowboy boots!
Fit & Features
- Denim fabric, stretchy knit shorts lining
- Strapless sweetheart neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Skater silhouette
- Pleated mini-length hem
- Runs small
Style Number/Barcode: 05102-000512
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, DENIM
Available Size: M, L
Product Badge:- Sale
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Definition Of Cute Off-The-Shoulder Mini Dress
Prance around like the cutie you are in this off-the-shoulder mini dress! The playful ruffles add movement and feminine charm while the flattering form-hugging silhouette showcases your curves.
Fit & Features
- Woven smocked stretchy fabric
- Ruffle off-the-shoulder neckline
- Form-hugging silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000096
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's A Wildflower Strappy Back Maxi Dress
Florals, fits, and full-on main character vibes. This floral mesh maxi dress hugs you in all the right places with a flirty strappy back and a vacay allure!
Fit & Features
- Floral print, mesh fabric, soft stretchy knit lining
- V-neckline
- Bungee strappy open back
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000097
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smooth Talker Strapless Bodycon Midi Dress
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000724
Category Name: Casual Dresses
Price: $21.96 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN-2, IVORY, PLUM
Available Size: XS, S, M, L
Product Badge:- Sale
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Too Cute to Care Babydoll Mini Dress
Low effort, high reward kind of vibe. This babydoll mini dress features a strappy cutout back and hidden pockets—aka your new throw-on-and-slay essential.
Fit & Features
- Poplin woven fabric
- Square neckline
- Spaghetti straps
- Spaghetti strap tie-back and cutout accent
- Hidden side pockets
- Babydoll silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000092
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cheerful Cutie Gingham Skater Dress
From casual plans to picnics, this cheery gingham dress will have you feeling cute all day long! This delightful dress is designed with a smocked waist for a flattering fit, a cute mini-length hem, and a flared skater silhouette.
Fit & Features
- Gingham print, woven fabric, stretchy knit lining
- Sweetheart neckline with bust tie
- Adjustable spaghetti straps
- Stretchy smocked waist
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000093
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Head-Turning Flirt Bodycon Mini Dress
A bodycon mini dress that makes the perfect foundation to create flirty looks!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000086
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet On You Denim Halter Skater Dress
Too cute to handle, too flirty to forget. This denim skater dress brings all the charm with a trendy halter neckline, heart detail at the bust, and a twirl-worthy pleated silhouette. Perfect for rooftop brunches, weekend vibes, or a little crush-worthy moment.
Fit & Features
- Denim fabric, minimal stretch
- Sleeveless V-neckline, metal heart accent
- Tie-back halter straps, partially open back
- Hidden back zipper with hook-eye closure
- Drop waist
- Short pleated skater silhouette, built-in knit panty lining
- Runs true to size
Style Number/Barcode: 05102-000085
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes On The Floral Maxi Dress
All eyes on the floral. This strapless maxi dress turns up the heat with a bold bloom moment and a high side slit that knows how to make an entrance at parties and on vacay!
Fit & Features
- Statement floral print
- Mesh fabric lined with stretchy knit
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000083
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt On Arrival Denim Skater Dress
Made for flings, flirts, and feelin’ yourself. This trendy halter skater dress hugs you in all the right places with a playful bust cutout and a twirl-worthy drop waist—aka your weekend wardrobe’s new fave.
Fit & Features
- Denim fabric
- Sleeveless cross-front halter neckline, tie-back straps
- Bust cutout, metal heart accent
- Partially open back, hidden lower back zipper closure
- Drop waist
- Short pleated skater silhouette
- Runs small, size up recommended
Style Number/Barcode: 05102-000084
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow Getter Strapless Cutout Mini Dress
Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.
Fit & Features
- Rib knit stretchy fabric
- Strapless sweetheart tube neckline with hardware trim
- Cutout accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000033
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island It Girl One-Shoulder Cutout Maxi Dress
Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!
Fit & Features
- Tropical leaf print, smooth stretchy knit fabric, short lining
- One-shoulder neckline with hardware trim
- Side cutout bodice
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000082
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Abstract Effect Strapless Bodycon Mini Dress
Every head will turn towards you in this abstract mini dress designed in a flattering bodycon silhouette that hugs your curves just right!
Fit & Features
- Abstract print, mesh-lined stretchy fabric
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000078
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meet Your Match Striped Lace-Up Midi Dress
Your new stylish striped midi dress for casual soirees! Featuring a cutout bodice accented with sleek hardware trim, this dress offers a bold, modern edge. The lace-up open back adds a touch of allure, while the side slit offers effortless movement.
Fit & Features
- Striped pattern, texture knit fabric, stretchy knit lining
- High halter neckline, spaghetti strap tie
- Lace-up open back, lower zipper and hook-eye closure
- Cutout bodice with hardware trim
- Side slit
- Form-hugging silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000081
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Fantasy Strapless Cutout Maxi Dress
Easy to wear, impossible to forget! Make your entrance in this floral maxi dress designed with a flirty cutout and form-hugging fit that accentuates your figure.
Fit & Features
- Floral print, mesh-lined fabric
- Strapless neckline
- Cutout bodice
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000079
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sea Salt Vibes Halter Crochet Midi Dress
Your next vacay is calling, and this crochet midi dress will set the vibes! Embrace the sand and sun in this stylish dress designed with a flattering high neckline and form-hugging fit.
Fit & Features
- Crochet knit fabric, stretchy knit lining
- High halter neckline, spaghetti strap ties
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000028
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Look Puff Sleeve Ruffled Skater Dress
Create a charming look for weekend brunch in this eyelet knit skater dress with the cutest puff sleeves and ruffled mini-length silhouette!
Fit & Features
- Eyelet knit fabric, stretchy knit lining
- Square neckline
- Short puff sleeves, ruffled hems
- Drop waist
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000075
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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East Coast Girlie Button Linen Skater Dress
Pack for the perfect East Coast summer with this chic linen skater dress! Adorned with faux button accents and a ruffled mini-length hem, this dress will make you stand out in style.
Fit & Features
- Linen-blend woven fabric, woven lining, shorts lining
- Boat neckline
- Back zipper and hook-eye closure
- Faux button accents
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000073
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Best For Last Halter A-Line Denim Mini Dress
Be the talk of the town in this flirty denim mini dress perfect for festivals, concerts, or country bars! The plunging halter neckline shows some skin while the flattering A-line silhouette cinches your waist and flows into a flirty flared mini hem.
Fit & Features
- Denim fabric, moderate stretch
- Plunge halter V-neckline, tie straps
- A-line silhouette
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000070
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Paradise Halter Open Back Slit Midi Dress
Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.
Fit & Features
- Slinky knit fabric, smooth stretchy knit lining
- Halter cowl neckline, beaded spaghetti strap tie
- Open back with spaghetti strap tie
- Bodycon silhouette
- Slit accent, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000283
Category Name: Casual Dresses
Price: $32.00 $45.90
On Sale: Yes
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS
Product Badge:- Sale
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Take Me Away Tube Midi Dress
Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!
Fit & Features
- Texture knit cotton-blend fabric, moderate stretch
- Sweetheart strapless tube neckline
- Twist bust
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000018
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free