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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Spritz And Plans Strapless Mini Dress
This dress has "take me on vacay" written all over it! The playful print and easy strapless fit keep it light, while the flowy mini hem makes it perfect for enjoying a sunny day on your next getaway.
Fit & Features
- Garden fruit and veggie print, woven fabric, stretchy knit lining
- Strapless neckline, stretchy smocked bodice
- Fit and flare silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000615
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bad Decisions Denim Mini Dress
This dress definitely starts stories. The denim bodycon mini dress features lace-up side details and corset seam shaping that hugs close and pairs perfectly with boots, tiny bags, and plans that were never fully confirmed.
Fit & Features
- Denim fabric, slight stretch
- Strapless tube neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Side lace-up plackets with bungee cords
- Corset-seamed bodice
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-001126
Category Name: Casual Dresses
Price: $35.96 $59.90
On Sale: Yes
Availability: In Stock
Available Color: DENIM-2
Available Size: XS, S, M, L
Product Badge:- Sale
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Clean Cut Sleeveless Denim Mini Dress
Denim just got a sharper social calendar. This mini dress brings a sleeveless cut and seamed structure to a fitted shape that works for brunch, casual plans, or a low-key night out. Add hoops and your favorite heel when the day starts cute and ends somewhere better.
Fit & Features
- Washed denim fabrication with minimal stretch
- Sleeveless crew neckline
- Back zipper with hook-eye closure
- Seamed design
- Faux pocket accents
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000613
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Soft Spoken Statement Linen V Neck Maxi Dress
Quiet luxury, but make it cool girl. This linen V-neck maxi dress skims the body with an easy drape, delicate straps, and lace panel details that feel effortless for dinner plans, gallery nights, or that last-minute RSVP.
Fit & Features
- Lightweight linen blend fabrication
- Sleeveless v-neckline
- Adjustable spaghetti straps
- Lace panel inserts
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000614
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Short Sleeve Bodycon Midi Dress
Easy, clean, and ready for repeat wear, this style keeps the look simple without feeling basic. The fitted midi dress smooths over your shape with short sleeves and a back slit for effortless movement from day plans to dinner.
Fit & Features
- Smooth stretch rib knit fabric
- Crew neckline
- Short sleeves
- Body-hugging midi fit
- Back center slit detail
- Runs true to size
Style Number/Barcode: 05102-000612
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Sunset Stunner Mesh Strapless Midi Dress
Hot plans, zero overthinking—this dress just gets it. A sleek strapless mesh midi that hugs in all the right places and shows up ready for every RSVP on your calendar.
Fit & Features
Style Number/Barcode: 05102-000611
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Garden Party Glow Floral Halter Midi Dress
Soft, sweet, and lowkey stealing all the attention. This floral halter midi dress hugs just right with a flattering fit that’s perfect for brunch plans, date nights, or any last-minute invite.
Fit & Features
- Lightweight eyelet fabrication with soft lining
- Sleeveless halter neckline
- Delicate floral pattern
- Fitted bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000609
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Flare Paisley Skater Mini Dress
Your weekend lineup just got cuter. This paisley mesh skater dress features delicate straps and a flowy tiered hanky hem that moves with every step, making it an easy pick for any sunny day plans.
Fit & Features
- Paisley print, mesh-lined fabric
- V-neckline
- Adjustable spaghetti straps
- Flowy skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000610
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Raise A Toast Mesh Bodycon Midi Dress
Made for wedding invites, cocktail receptions, and the kind of nights that deserve extra photos. This strapless mesh midi dress sculpts your figure with flattering ruching and a draped side sash that brings the drama.
Fit & Features
- Mesh-lined fabric
- Strapless neckline
- Wrap side sash detail
- Back zipper closure, center back slit accent
- Ruched bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001186
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: LIGHT, BLUE-2
Available Size: XS, S, M, L, XL
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Vacation Flirt Knit Cutout Maxi Dress
Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.
Fit & Features
- Knit fabric with flame stitch pattern
- Sleeveless plunging V-neckline, beaded strap
- Tie-back halter straps
- Lace-up side cutouts
- Open back, lower tie-back spaghetti straps
- Back zipper and hook-eye closure
- Maxi-length bodycon silhouette, back slit accent
- Runs true to size
Style Number/Barcode: 05102-000606
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
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Island Nights Mesh Halter Maxi Dress
Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter V-neckline with hardware insert
- Tie straps, open back
- High front ruffled slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000607
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Hour Crochet Halter Dress
Booked for golden hour and not coming back early. This crochet halter mini dress features floral appliqué and a lace-up back that keeps things effortlessly pretty with just enough detail to stand out.
Fit & Features
- Crochet texture-lined knit fabric
- Halter plunge neckline with beaded strap
- Open back with lace-up design
- Floral applique
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000605
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brown Sugar Breeze Cutout Maxi Dress
This strapless maxi dress brings the kind of effortless allure that looks good from beach strolls to walks back to the hotel. The smocked fit, soft cutout detail, and flowy skirt keep it stylish with a pair of sandals.
Fit & Features
- Gauze woven fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice with cutout
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000602
Category Name: Casual Dresses
Price: $25.97 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: S
Product Badge:- Sale
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Small Town Stunner Denim Mini Dress
Giving county fair flirt with a side of sassy. This strapless denim mini dress mixes corset-inspired seam detailing with a tiered poplin hem that makes every head turn. Pair with sandals for any sunny day plans or events.
Fit & Features
- Denim fabric, slight stretch
- Strapless sweetheart neckline, poplin ruffle trim, non-slip grip lining
- Padded bra cups, back zipper and hook-eye closure
- Corset-inspired seam detailing
- Bodycon fit
- Poplin side ruffle panels, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000603
Category Name: Casual Dresses
Price: $69.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Cool Confidence Animal Print A-Line Mini Dress
A little wild, a lot unforgettable. This strappy abstract animal print A-line mini dress skims and sways with every step, giving you that effortless, throw-it-on-and-own-the-night kind of confidence.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract animal print
- Sleeveless sweetheart neckline, no-slip strip
- Cross-front spaghetti strap design leading to a tie-back halter design
- Open back design
- Mini-length asymmetric hem, flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000823
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirting With Drama Lace Ruffle Skater Dress
A little lace, a lot of attitude. This sheer lace skater dress hugs at the top and flares into flirty, ruffled layers that make every step feel like a moment.
Fit & Features
- Sheer lace fabric with partial knit lining, moderate stretch
- Strapless bodice with smooth woven fabric with sheer lace inserts and trim
- Sweetheart neckline, front hook-eye closures
- Open lace-up back design with tie closure
- Drop waist seam, tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05103-000824
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Sale
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Coconut Coast Cutout Maxi Dress
Booked the trip and packed this tropical maxi dress that brings vacay vibes with a smocked fit, breezy skirt, and just the right amount of skin-baring detail. Pair with sandals and sunnies.
Fit & Features
- Tropical palm print, gauze-woven fabric
- Strapless sweetheart neckline
- Ruched drawstring tie-front bodice
- Cutout accent
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000601
Category Name: Casual Dresses
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Confidence Sheer Lace Maxi Dress
A little sheer, a little bold—exactly how you like it. This lace maxi dress skims your body with a soft stretch feel, made for slipping into when the vibe calls for effortless confidence.
Fit & Features
- Textured lace fabric with a mini-length knit lining, moderate stretch
- Sleeveless V-neckline with O-ring accent at the bust
- Adjustable spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000599
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple Charm Gingham Mini Dress
Feels like a picnic invite just showed up. This gingham mini dress keeps it cute and easy with a collar, cap sleeves, and a button-down front that works from coffee shop hangs to casual plans.
Fit & Features
- Gingham pattern, cotton-blend woven fabric, woven lining
- Collar neckline
- Cap sleeves
- Front button-down closures
- Tie-back strap
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000598
Category Name: Casual Dresses
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Away Strapless Maxi Dress
This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.
Fit & Features
- Chevron pattern, crochet fabric, smooth knit lining
- Strapless neckline
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000595
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
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Twice As Nice Halter Ruffle Mini Dress
Date night just found its favorite dress. This halter mini dress serves a plunging neckline and a tiered ruffle skirt that moves with you from cocktails to the dancefloor.
Fit & Features
- Lace-lined fabric
- Plunge halter neckline
- Open back
- Form-hugging fit
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000816
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daydream Detour Paisley Maxi Dress
Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.
Fit & Features
- Floral paisley print, woven fabric, short woven lining
- V-neckline, spaghetti straps
- Open tie-back
- Center front button-up closures
- Flowy maxi silhouette, sheer lace trim
- Runs true to size
Style Number/Barcode: 05102-000592
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Center Of Attention Floral Maxi Dress
This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.
Fit & Features
- Statement floral print, lined mesh fabric, high stretch
- Strapless tube neckline
- Curve-hugging, mermaid fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000593
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, L
Product Badge:- Sale
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Coast To Cocktails Striped Maxi Dress
The dress that belongs in your vacation photo dump. With a plunging halter neckline, textured striped knit, and an open tie-back design, this maxi dress was made for ocean views, dinner reservations, and weekend escapes.
Fit & Features
- Striped pattern, sheer texture crochet knit fabric
- Halter neckline, tie straps
- Open tie-back
- High side slit
- Curve-hugging, long hem
- Runs true to size
Style Number/Barcode: 05102-000591
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Sale