Casual Dresses

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.

  • Take Me Somewhere Maxi Dress

    Currently accepting compliments and vacation invitations. This halter maxi dress hugs in all the right places with a plunging neckline and open back that feels made for dinners, destination weddings, and packed itineraries.

    Fit & Features

    • Stitched striped pattern, knit fabric, knit lining
    • Plunge halter neckline
    • Open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000643

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

  • Getaway Glam Tropical Floral Maxi Tube Dress

    One dress, endless compliments. This tropical floral maxi tube dress combines a sleek bodycon fit with oversized blooms for a look that feels both getaway and glam.

    Fit & Features

    • Knit fabric with lining, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000644

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Sweet Ruffle Skater Dress

    Consider this your excuse to romanticize even the simplest plans. The ruffle skater dress hugs up top with a soft stretch fit, then flows into that twirl-ready skirt made for brunch dates, parties, and everything in between.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless V-neckline, ruched bust
    • Adjustable spaghetti straps
    • V-shaped drop waist seam
    • Asymmetric tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001227

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: M

  • Second Look Polka Dot Mesh Midi Dress

    Absolutely dressed with somewhere to be. This polka dot mesh midi dress serves a sleek bodycon fit with a draped cowl neckline and open tie-back for plans that deserve a second look.

    Fit & Features

    • Mesh fabric with full-length knit lining, high stretch
    • Polka dot print
    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Open back, tie-back spaghetti straps
    • Side zipper and hook-eye closure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000815

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • City Crush Polka Dot Lace Maxi Dress

    Caught feelings… for this dress. This polka dot slip maxi dress hugs just right with a sleek silhouette that’s made for dinners, drinks, and a little lingering eye contact.

    Fit & Features

    • Lightweight woven knit fabrication
    • Sleeveless v-neckline
    • Contrast lace trim bodice
    • Polka dot pattern
    • Slip silhouette styled fit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-001218

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blue Skies And Late Nights Mini Dress

    This is the dress that makes every summer plan feel a little more exciting. Featuring a breezy bandana-inspired print, open-back halter neckline, and flirty skater silhouette, it's made for vacation dinners, sunset strolls, and saying yes to plans that weren't on the calendar.

    Fit & Features

    • Paisley print, chiffon fabric, woven lining
    • Halter neckline, spaghetti straps
    • Open back
    • Stretchy smocked waist panel
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000641

    Category Name: Casual Dresses

    Price: $15.00

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunlit RSVP Lace Ruffle Romper

    Soft lace, flirty ruffles, and that open-back tie moment make this halter romper perfect for showers, brunch, and vacations. Light, pretty, and impossible to ignore—in the best way.

    Fit & Features

    • Lace-lined fabric
    • Plunge halter neckline, tie straps
    • Strappy open back with tie
    • Form-hugging fit
    • Ruffled tiered mini-length hem
    • Stretchy knit shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000263

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed Stunner Halter Maxi Dress

    Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.

    Fit & Features

    • Artsy print, woven fabric
    • Halter neckline
    • Strappy cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000645

    Category Name: Casual Dresses

    Price: $13.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirting With Florals Mini Dress

    Cute enough to cause a few double takes. This floral tube mini dress hugs in all the right places with a sleek bodycon fit that’s made for brunch dates, weekend plans, and wineries.

    Fit & Features

    • Dainty floral print, eyelet knit-lined fabric
    • Strapless tube neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000638

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City After Sunset Paisley Midi Dress

    A midi dress for any occasion! This strapless mesh midi dress hugs in all the right places with a moody paisley print and a flirty front slit for effortless movement and allure.

    Fit & Features

    • Paisley print, mesh fabric, smooth lining
    • Tube strapless neckline
    • Front slit
    • Form-hugging fit
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000637

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Bloom Floral Knit Midi Tube Dress

    Big blooms, bold plans. This floral knit midi tube dress hugs in all the right places with a sleek bodycon fit and effortless strapless neckline—perfect for brunch dates, rooftop drinks, or any moment that deserves a standout look.

    Fit & Features

    • Ribbed knit fabric, moderate stretch
    • Large floral print
    • Strapless neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000344

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Sale
  • 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, M, L

    Product Badge:
    • Sale
  • 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
  • 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
  • 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, M, L

    Product Badge:
    • Sale
  • 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
  • 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
  • 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: In Stock

    Available Color: BROWN

    Available Size: XS

    Product Badge:
    • Sale
  • 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
  • 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: 05102-000620

    Category Name: Casual Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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