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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Late Dinner Plans Tube Maxi Dress
This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.
Fit & Features
- Soft jersey knit fabric, stretchy lining
- Strapless tube neckline, non-slip grip lining
- Ruched fitted bodice
- Flowy curve-hugging silhouette
- Shark-cut maxi hem
- Runs true to size
Style Number/Barcode: 05102-000787
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Booked Midi Dress
The kind of dress that makes last-minute reservations feel completely intentional. This open back midi dress combines a sleek body-skimming fit with a draped sash detail for an elevated look that works everywhere from cocktail parties to weddings.
Fit & Features
- Slinky knit double-lined fabric
- Sleeveless boat neckline
- Open back, center back slit
- Form-hugging midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000816
Category Name: Casual Dresses
Price: $25.96 $42.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- Sale
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Weekend Romance Floral Cotton Midi Dress
Feels like a soft yes to every plan on your calendar. This flowy ruffle midi dress brings an easy, romantic fit with a smocked waist and tie back, perfect for brunch, showers, or vacations.
Fit & Features
- Dainty floral pattern, cotton woven fabric and lining
- Sleeveless ruffle trim V-neckline
- Button front bust accents, stretchy smocked panel
- Tie-back design
- A-line silhouette, ruffled midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001392
Category Name: Casual Dresses
Price: $27.96 $64.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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RSVP To Sunshine Striped Mini Dress
This striped halter mini dress hugs in all the right places with a flattering curve-hugging fit that’s made for brunch, beach city strolls, and vacations.
Fit & Features
- Striped pattern, ribbed knit fabric, knit lining, high stretch
- Halter V-neckline with tie straps
- Partially open back
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000785
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
Product Badge:- Sale
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Chic Agenda Plunge Maxi Dress
From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.
Fit & Features
- Smooth knit stretch fabric
- Cao sleeves with shoulder pads for structure
- Plunge V-neckline
- Center front drape and slit designs
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000784
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Eyelet Lace Skater Mini Dress
Romantic details make this dress feel polished. The lace bodice and embroidered eyelet skirt create rich texture, while the scalloped hem adds a delicate finish. It’s an easy pick for brunches, showers, and daytime celebrations.
Fit & Features
- Airy cotton-blend woven fabric with lining, no stretch
- V-neckline with ruffled trim, wide tank straps
- Sheer lace bodice with embroidered detailing, lined bust
- Front hook-eye closures
- Smocked back panel
- Eyelet skater mini-length skirt with scalloped hem
- Runs true to size
Style Number/Barcode: 05102-000783
Category Name: Casual Dresses
Price: $27.96 $45.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: S, M, L
Product Badge:- Sale
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Pretty Little Tie-Back Skater Dress
The kind of dress that makes plans for you. This chiffon skater dress with a sweetheart neckline, lace trim, and tie-back detail feels light, flirty, and ready for any plans.
Fit & Features
- Swiss dot chiffon fabric, smooth woven lining
- Sweetheart lace trim neckline
- Adjustable spaghetti straps
- Open tie-back design, stretchy smocked panel
- Sheer lace trim waist insert
- Skater silhouette, lace trim ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000779
Category Name: Casual Dresses
Price: $42.00 $59.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Polka Dot Plans Ruffle Mini Tube Dress
The dress code? Looking effortlessly put together. This polka dot mini tube dress combines a curve-hugging fit with a playful, ruffled, A-line hem, making it an easy pick for brunch dates, party invites, and any excuse to wear something cute.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Polka dot print
- Strapless straight-across neckline
- Drop waist
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000780
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: M, L
Product Badge:- Sale
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Flirty Confidence Lace One-Shoulder Mini Dress
A little bold, a little soft—exactly the balance you were going for. This lace one-shoulder A-line mini dress hugs up top and flares at the hem, giving you that confident, caught-in-the-moment kind of vibe.
Fit & Features
- Lace fabric with knit lining, high stretch
- Sleeveless one-shoulder neckline, tank straps
- Fitted bodice, ruched detailing
- Drop waist design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000778
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: YELLOW
Available Size: S, M, L
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Polished But Fun Skater Mini Dress
Clean, classic… and cuing all the compliments. This striped skater mini dress brings that tailored, put-together vibe with a cinched bodice and flared skirt perfect for sunny days.
Fit & Features
- Striped pattern, linen-like woven fabric
- Square neckline, spaghetti straps
- Hidden side pockets
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000776
Category Name: Casual Dresses
Price: $40.00 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Retro Crush Floral Chiffon Mini Dress
Serving vintage flirt energy in this floral mini dress. It brings the vibe with a breezy A-line fit, playful cutouts, and a tie-front bust made for sunny days.
Fit & Features
- Vintage-inspired floral print
- Chiffon fabric, smooth woven lining
- V-neckline, tie-front bust, adjustable spaghetti straps
- Stretchy smocked back panel
- Side cutouts along the bodice
- A-line fit, ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000775
Category Name: Casual Dresses
Price: $20.96 $49.90
On Sale: Yes
Availability: In Stock
Available Color: LAVENDER
Available Size: S, M, L
Product Badge:- Sale
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Sculpted Ease Ruched Midi Dress
The gathered texture gives this silhouette its sculpted appeal. This drop-waist midi dress features a ruched bodice and underwire bust insert that bring definition to the softly flared shape. The structured detailing adds polished impact without overwhelming the clean finish.
Fit & Features
- Cotton-blend knit stretch fabric
- Sewn-in knit bodice lining
- Ruched fitted strapless bodice, non-slip grip lining
- Underwire bust insert
- Drop waist seam, side slit accent, flowy midi-length hem
- Back zipper with hook-and-eye closure
- Runs true to size
Style Number/Barcode: 05102-000774
Category Name: Casual Dresses
Price: $56.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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West Coast Icon LA Bodycon Mini Dress
West coast icon, LA attitude. This bodycon mini dress hugs your shape with a soft, stretchy feel that moves with you from game day to spontaneous plans.
Fit & Features
- Ribbed cotton-blend knit fabric, high stretch, knit lining
- Sleeveless crew neckline, contrast trim
- Tank shoulder straps
- "Los Angeles" front embroidered script
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000772
Category Name: Casual Dresses
Price: $19.96 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Sale
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Game Day Crush LA Bodycon Mini Dress
Serving varsity vibes with zero effort required. This bodycon mini dress hugs in all the right places with a sporty crewneck design that’s made for stadium games and casual hangs.
Fit & Features
- Knit cotton fabric, high stretch, knit lining
- Striped crew neckline
- Striped short sleeves
- "Los Angeles" front embroidered script
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000771
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
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Prep Shift Button-Down Contrast Skater Mini Dress
The contrast bodice gives this mini dress its standout look, adding a sleek fitted layer over the striped button-down design. The collared neckline and long sleeves keep the shape polished, while the skater skirt adds a softer finish below. Style it with pointed heels and bold hoops for a trend-forward look with a preppy twist.
Fit & Features
- Striped woven fabric
- Collared button-down neckline
- Long sleeves with button details
- Knit contrast fitted bodice
- Ruched waist
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000773
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Daydreaming Floral Knit Dress
Equal parts cozy and cute, this floral midi dress is made for brunch, weekend plans, and vacations. The oversized floral design gives it a playful statement feel, while the strapless silhouette keeps the look effortlessly polished.
Fit & Features
- Statement floral print, sweater knit fabric
- Strapless tube neckline
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000411
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Meet Me In Maui Mesh Maxi Dress
Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.
Fit & Features
- Tropical print, lined mesh fabric with stretch
- Strapless neckline
- Bodycon silhouette
- Fitted maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000763
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Product Badge:- Sale
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Rebel Twirl Frayed Denim Ruffle Mini Dress
Denim gets a flirtier update with a strapless shape, frayed trim, and tiered ruffles. The A-line silhouette keeps the look playful, while the distressed edges give it a more directional finish. Style it with sculptural heels or statement boots to lean into the trend.
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight-across neckline
- Studded seam detailing, frayed trim
- Exposed back zipper with hook-eye closure
- Tiered ruffle design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000767
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Sultry Edge Faux Suede Halter Mini Dress
Low-cut confidence, no apologies. This sultry faux suede halter mini dress hugs just right with a plunging cowl neck and open back that are both daring and effortless.
Fit & Features
- Faux suede fabric, moderate stretch
- Rhinestone and studded trim
- Sleeveless plunging cowl neckline
- Halter tie-back straps
- Open back, lower cross-back design
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000862
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Romance Lace A-Line Mini Dress
Romance, with a little edge. This lace A-line mini dress mixes a flirty tie-front, ruffled trim, and an effortless flowy shape that works for date nights, parties, and whatever gets added to the group chat.
Fit & Features
- Lace fabric with knit lining, moderate stretch
- Sleeveless V-neckline, tie-front detail
- Adjustable spaghetti straps
- Ruffled trim
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000755
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Easy Escape Textured Stripe Halter Dress
Made for sunshine-filled plans and easy outfit decisions. This textured stripe dress features a smocked halter bodice and a softly flared skirt that creates beautiful movement with every step. Perfect for beach vacations, brunch dates, and warm-weather weekends that call for effortless style.
Fit & Features
- Texture striped knit fabric, partial knit lining
- Halter neckline with tie straps
- Open back
- Flowy silhouette with a ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000753
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Romance Floral Ruffle Mini Dress
Romantic, but still a little playful. This floral mesh halter mini dress features a plunging neckline and tiered ruffle hem with a sash detail that moves effortlessly from brunch plans to sunset drinks.
Fit & Features
- Floral print, mesh-lined stretchy fabric
- Plunge halter neckline with tie strap
- Open back design with tie strap
- A-line silhouette, ruffled trim detail
- Side ruffled drape
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001337
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Attention Floral Tube Mini Dress
Booked the trip just to wear this dress. The bold tropical floral print and bodycon silhouette will make heads turn at the beach clubs, island resort, or a weekend pool party!
Fit & Features
- Statement floral print, knit-lined stretchy fabric
- Strapless tube neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000751
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Sale
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Major Fling Flutter Sleeve Maxi Dress
Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.
Fit & Features
- Airy cotton fabric, woven lining
- Flutter short sleeves
- V-neckline
- Cutout back
- Ruffled tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000748
Category Name: Casual Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free