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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Sweet Heat Tube Maxi Dress
This strapless rib knit bodycon maxi dress hugs you just right and features a side floral crochet accent that feels equal parts flirty and elevated for dinners, birthdays, and any weekend plans.
Fit & Features
- Rib knit fabric with stretch
- Strapless neckline
- Side floral crochet accent
- Bdoycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000345
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Plans Striped A-Line Midi Dress
Plans made themselves. This striped flowy A-line midi dress keeps it breezy with a smocked high waist, adjustable straps, and an effortless silhouette that works for brunch, day dates, and last-minute invites.
Fit & Features
- Striped texture woven fabric
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Smocked high waist, hidden side seam pockets
- Midi-length hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000812
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: In Stock
Available Color: SAGE
Available Size: S, M, L, XL
Product Badge:- Sale
- Striped texture woven fabric
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Bare It Back Knot Detail Mini Dress
Business in the front, drama in the back. This mini dress keeps it sleek with a high neckline and bodycon fit, then flips the script with an open back moment perfect for turning heads.
Fit & Features
- Soft stretch knit fabric
- Mock neckline with cap sleeves
- Twist front knot detail at waist
- Open back cutout design
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000635
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Passport Ready Sequin Sheer Knit Maxi Dress
Vacation photos called—they want this dress in every frame. This sequin embroidered sheer knit maxi dress pairs a sculpting bodycon fit with a striking hardware cutout and leg-baring slit that was made for rooftop dinners, destination weddings, and every RSVP in between.
Fit & Features
- Sheer textured knit fabric, mini-length knit lining, moderate stretch
- Sequin embroidery
- Strapless sweetheart neckline, bust cutout with asymmetric metal hardware accent
- Open tie-back design
- Maxi-length hem with high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000632
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S
Product Badge:- Sale
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Tropic Heat Floral Mini Dress
Serving vacation energy even if you’re not booked yet. This floral mesh dress contours your shape with a plunging neckline and open back that does all the talking.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000625
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blush Blossom Halter Mini Dress
A little flirty mini dress, a little romantic, and made for sunny plans. This embroidered floral halter mini dress features a soft A-line shape that skims the body, while the delicate tie front and open back keep the look playful.
Fit & Features
- Embroidered floral woven fabric
- Halter neckline with adjustable tie
- Front tie detail at bust
- A-line silhouette with mini-length hem
- Hidden back zipper closure
- Runs true to size
Style Number/Barcode: 05102-000630
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Rush Tropical Floral Mini Dress
Booked trip or just booking attention, this tropical floral ruffle mini dress gets the invite. The stretchy lined mesh, halter cowl neckline, open back, and flowy ruffled sash bring flirty movement with a fitted A-line shape.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Asymmetric tiered ruffled design, ruffled side sash accent
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000624
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, L
Product Badge:- Sale
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Paradise Found Halter Mini Dress
Straight into the vacation outfit folder. This textured knit mini dress features playful side cutouts and cascading bead details that bring just the right amount of drama to beach cabanas, tropical dinners, and every photo-worthy plan.
Fit & Features
- Texture knit fabric, smooth kint lining
- High halter neckline, tie straps
- Open tie-back, lower zipper and hook-eye closure
- Side cutouts with beaded fringe trim
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000628
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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Island Heat Mesh Maxi Dress
Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.
Fit & Features
- Tropical floral print, mesh fabric, brushed knit lining
- Strapless tube neckline, non-slip grip lining
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000626
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Second Glance Beaded-Trim Halter Midi Dress
The kind of dress that gets a second glance before you even say a word. This beaded-trim halter midi dress hugs in all the right places with a textured knit feel, open lace-up sides, and an open back that makes every entrance look intentional.
Fit & Features
- Textured knit fabric, high stretch, knit lining
- Sleeveless V-neckline, beaded bar strap accent
- Tie-back halter spaghetti straps, beaded accents
- Open back, lower tie-back spaghetti straps, back zipper closure
- Open lace-up side design
- Midi-length hem, back slit detail, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000627
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay State Of Mind Tropical Print Maxi Dress
Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.
Fit & Features
- Knit fabric with high stretch, soft knit lining
- Tropical print
- Strapless neckline
- Triple bust cutouts and oval-shaped hardware accents
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000622
Category Name: Casual Dresses
Price: $14.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Corset Code Lace-Up Denim Skater Dress
The lace-up sides bring the attitude. This skater mini dress mixes denim structure, grommet hardware, and a strapless neckline for a fitted-to-flared look with major detail payoff. Wear it for concerts, parties, and weekend fun.
Fit & Features
- Structured denim fabrication, built-in knit panty lining
- Strapless sweetheart neckline, non-slip grip lining
- Lace-up side details with grommet hardware
- Fitted bodice with flared skater skirt
- Back zipper and hook-eye closure
- Runs true to size
Style Number/Barcode: 05102-000826
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: DARK, DENIM-2
Available Size: XS, S, M, L
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Miss Me Yet Abstract Babydoll Mini Dress
Serving just enough cuteness with every step. This abstract print chiffon babydoll dress features a plunge V-neckline with studded trim and an open back that practically guarantees compliments before you even make it to dinner.
Fit & Features
- Abstract print, chiffon fabric, smooth woven lining
- Plunge V-neckline with a studded trim bust
- Open back, adjustable spaghetti straps
- Babydoll mini-length silhouette, hanky hem
- Runs true to size
Style Number/Barcode: 05103-000851
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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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: $59.90
Availability: In Stock
Available Color: DENIM-2
Available Size: XS, S, M, L
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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. knit lining
- Sleeveless v-neckline
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- 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: XS, 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
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