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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Salt Air Striped Knit Cutout Maxi Dress
Vacation photos are optional, but compliments won't be. This striped knit cutout maxi dress hugs your curves with statement O-ring details and a leg-baring slit that was made for turning heads.
Fit & Features
- Abstract striped textured knit fabric, moderate stretch
- Sleeveless sweetheart neckline
- O-ring halter design, tie-back halter spaghetti straps
- Waist cutout with O-ring design
- Open back, bar strap with hook-eye closure, lower back zipper closure
- Maxi-length hem, high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000590
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Café Date Polka Dot Midi Dress
A little flirty, a little polished, and ready for wherever the day takes you. This polka dot midi dress combines a flattering lace-up corset bodice, sweetheart neckline, and leg-baring slit for an effortless look for brunch, showers, or weekend plans.
Fit & Features
- Polka dot pattern, linen-blend woven fabric, woven lining
- Drawstring bust tie square neckline
- Adjustable shoulder straps
- Side zipper and hook-eye closure, lace-up back detail
- Corset bodice, flexible boning, drop waist seam
- Front slit, A-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000587
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M
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Spice Done Right Mesh Midi Dress
Too good to save for just one occasion. This mesh midi dress hugs every curve with ruched detailing and a strapless neckline that makes the whole dress feel a little extra in the best way.
Fit & Features
- Mesh-lined fabric
- Strapless sweetheart neckline
- Back zipper closure
- Bodycon silhouette, ruched detail
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000588
Category Name: Casual Dresses
Price: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Extra Flirty Ruffle Mini Dress
This is the mini dress you wear when you want something a little extra. The plunging halter neckline, open back, and ruched drop waist hugs your curves, while the tiered ruffle skirt keeps it flirty for parties, birthdays, and spontaneous nights out.
Fit & Features
- Smooth knit fabric with high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Ruched drop waist
- Tiered ruffled design
- Mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000811
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: NAVY, LIGHT, BLUE, RUST-2
Available Size: S, L, M, XS
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She's Bold Abstract Floral Midi Tube Dress
Fit & Features
- Sleek knit fabric, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Ruched detailing
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000585
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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One More Pic Button Denim Dress
Serving attitude with every button. This denim mini dress hugs in all the right places with a lace-up back that makes the exit just as good as the entrance.
Fit & Features
- Denim fabric, vintage-inspired wash, high stretch
- Sleeveless baot neckline
- Front button-up closures
- Tailored seams
- Cutout lace-up strappy back
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000586
Category Name: Casual Dresses
Price: $29.96 $49.90
On Sale: Yes
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
Product Badge:- Sale
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Flirty Fit Lace Ruffle Romper
The one that instantly upgrades whatever’s on your calendar. A lace cutout ruffle romper with a flirty fit that’s made for parties, birthdays, and last-minute invites you’re definitely saying yes to.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Sleeveless plunging V-neckline, bar strap accent
- Halter tie-back spaghetti straps
- Open back, lower tie-back spaghetti straps
- Drop waist
- Tiered ruffled mini-length overlay, skater silhouette, hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000252
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: S, M, L
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Brunch Booked Floral Mini Dress
Serving vacation mood before you've even packed a bag. This floral tube mini dress features a flattering A-line fit that feels effortless for brunch, parties, and every warm-weather plan that pops up.
Fit & Features
- Floral print, lined knit fabric
- Strapless tube neckline
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000581
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: S
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Darling Detail Strapless Midi Dress
Clean lines, zero effort, maximum compliments. This strapless midi dress hugs in all the right places with a textured knit feel that makes dinner plans, celebrations, and last-minute invites look very handled.
Fit & Features
- Textured knit-lined fabric
- Strapless neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000578
Category Name: Casual Dresses
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Ready Floral Print Maxi Dress
Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!
Fit & Features
- Smooth knit stretchy fabric, knit lining
- Halter plunge neckline, hardware insert, adjustable cross back straps
- Open back design
- Cutout bosdice
- Flowy maxi-length silhouette with floral hem print
- Runs true to size
Style Number/Barcode: 05102-000576
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Charm Flower Strap Crochet Mini Dress
Serving shape with a side of charm. This crochet mini dress hugs your curves while the flower strap detail brings just enough sweetness—wear it when you want compliments without trying.
Fit & Features
- Crochet knit fabric with knit lining, moderate stretch
- Lettuce edge trims
- Sleeveless V-neckline
- Adjustable spaghetti straps, front flower accents
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000318
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Styled Chic Button Halter Neck Mini Dress
Serving sculpted and styled without trying too hard. This halter neck mini dress hugs your curves with a sleek ribbed feel and subtle button detail that keeps it chic from every angle.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless V-neckline
- Varied button accents
- Halter strap, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000316
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Postcard From Paradise Maxi Dress
Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.
Fit & Features
- Multi-printed design, woven fabric
- V-neckline with trim and tie bust
- Spaghetti straps
- Lace-up tassel back
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000572
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pearls Before Midnight Denim Mini Dress
A little country, a little glamorous, and fully committed to being overdressed. This denim skater mini dress brings together pearl embellishments, a fitted bodice, and flirty volume for the kind of outfit that owns the room before you even say hi.
Fit & Features
- Denim fabric, bust lining
- Sweetheart neckline, adjustable spaghetti straps
- Button front accents. back zipper and hook-eye closure
- Skater silhouette
- Faux pearl embellishments
- Pleated side mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000568
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Plans Tropical Tube Mini Dress
Booked, busy, and already packing this. This floral print mini dress hugs you in all the right places and was made for beach stays, resort destinations, and tropical escapes!
Fit & Features
- Slinky knit-lined stretchy fabric
- Tube strapless neckline
- Statement floral print
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000571
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Sweet Talker Floral Eyelet Midi Tube Dress
Soft, fitted, and low-key stealing attention. This floral print eyelet midi tube dress hugs in all the right places with a stretchy feel that’s made for brunch plans, day dates, and everything after.
Fit & Features
- Eyelet knit fabric with sewn-in knit lining, high stretch
- Floral print
- Strapless elasticized straight-across neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000569
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Muse Floral Midi Dress
Soft florals and a sleek silhouette make this one an instant favorite. This strapless floral eyelet bodycon midi dress hugs your curves and adds a polished look for brunch, garden parties, and getaways.
Fit & Features
- Ditsy floral print, eyelet knit fabric, soft lining
- Strapless tube neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000570
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Styled Up Off-Shoulder Mini Dress
Easy, confident, and styled without overthinking. This off-the-shoulder blouson mini dress drapes up top with a fitted bottom that keeps the silhouette clean and pulled together for any plans that pop up.
Fit & Features
- Soft knit fabric with comfortable stretch
- Relaxed blouson top with a fitted mini skirt
- Off shoulder neckline
- Relaxed short sleeves
- Runs true to size
Style Number/Barcode: 05102-000737
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: YELLOW
Available Size: M
Product Badge:- Sale
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Soft Glow Bodycon Mini Dress
Cute, simple, and effortlessly flattering. This ribbed knit bodycon mini dress hugs in all the right places with a clean square neckline and delicate straps, making it the perfect dress for day dates, brunch, or a casual night out.
Fit & Features
- Rib knit fabric, sewn-in lining
- Square neckline
- Spaghetti straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000560
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wine Night Pinstripe Mini Dress
Clock out, but keep the attitude. This pinstripe mini dress brings tailored energy up top and flirty drama at the hem, hugging you in all the right places for wine bar nights and dinner.
Fit & Features
- Pinstriped pattern, woven fabric, sewn-in knit lining
- Strapless lace trim sweetheart neckline
- Padded bra cups
- Back zipper and hook-eye closure
- Ruched side lace panels
- Form-hugging fit, ruffled mini hem
- Runs true to size
Style Number/Barcode: 05102-000558
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Chic Cutout Maxi Dress
The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.
Fit & Features
- Gauze cotton woven fabric, woven lining
- Sweetheart neckline, spaghetti straps
- Open tie-back design
- Cutout bodice
- Hidden side pockets
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000559
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Vibe Ribbed Knit Mini Tube Dress
Simple, chic, and such a vibe. This ribbed knit mini tube dress hugs your curves with a comfy stretch fit—made for plans that come together at the last minute, but you still look fab.
Fit & Features
- Hacci ribbed knit fabric, high stretch, knit lining
- Strapless fold-over neckline
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000562
Category Name: Casual Dresses
Price: $21.96 $35.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
Product Badge:- Sale
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Flirting In Positano A-Line Mini Dress
Meet the dress equivalent of booking the flight before asking questions. With its dreamy coastal print and easy strapless fit, this mini dress was made for European getaways, brunch, and sunny day plans.
Fit & Features
- Multi-print design, linen-blend woven fabric, woven lining
- Strapless neckline, non-slip grip lining
- Side hidden zipper and hook-eye closure
- Bar back accent and cutout
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000561
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Plans Ahead Long Sleeve Skater Dress
Soft, cute, and already booked. This ribbed skater dress hugs up top and floats just right at the hem, making it an easy yes for brunches, daytime plans, and V-day dates!
Fit & Features
- Pointelle knit soft stretch fabric
- Crew neckline
- Fitted long sleeves
- Fitted bodice with a defining drop waist seam
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000556
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free