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.

  • Cold Brew Collared Mini Dress

    For coffee dates and everything else, you'll adore this collared v-neck mini dress designed to flatter your figure on a bodycon silhouette with a faux button-down accent and all-over ruching. Composed of sleek knit fabric with a moderate stretch. Finish the look in cute booties.

    Fit & Features

    • Sleeveless, collared v-neck
    • Faux button-down placket
    • All-over ruching
    • Bodycon silhouette
    • Mini-length hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4482

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chain Reaction Rib Knit Dress

    This rib knit dress may cause a chain reaction of followers! It features a sleeveless square neckline, edgy chain-link straps, and a bodycon mini-length hem. Complete the look in platform heels for girl's night.

    Fit & Features

    • Sleeveless square neckline
    • Chain-link shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4480

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Look Floral Mini Dress

    Get the cutest look for the spring season with this adorable floral mini dress! It features a sleeveless sweetheart neckline with shirring at the bust, spaghetti straps, a short, curve-hugging fit, and an all-over dainty floral print pattern. Style this dress with a cropped denim jacket and strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Shirring at the bust
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Floral print
    • Brushed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4612

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Sweetheart Midi Dress

    Sweet but sexy, this denim midi dress was made for you! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, corset-style bodice, and a high-waist seam leading to the bodycon silhouette with a back slit accent. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Corset-style bodice, back zipper closure
    • High-waist seam, back slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4477

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daisy Darling Sleeveless Short Dress

    Fall into a daisy daze with a short dress that brings all the feels! The dress features a sleeveless square neckline with lace trim, spaghetti straps, a pretty daisy print, and a short-length hem. The dress is composed of a brushed knit fabric with a form-hugging fit and moderate stretch. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless square neckline, lace trim
    • Spaghetti straps
    • Daisy floral print
    • Short length hem
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4479

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Accents Bodycon Mini Dress

    You'll love the alluring accents of this trendy-chic bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, a revealing side cutout at the waist, ruching down one side with an adjustable drawstring, and a short, curve-hugging fit. The smooth knit fabric features an all-over snake print pattern. Style this dress with clear heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side cutout at the waist
    • Ruching down one side, adjustable drawstring
    • Bodycon silhouette, mini hem
    • Snake print, lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4473

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect For Paradise Midi Dress

    This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length asymmetrical hem
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4474

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Mini Dress

    You'll always look on point in this trendy ruched mini dress! It features a sleeveless square neckline, bungee straps, a high waist seam, side ruched detailing with adjustable drawstrings, and a short, curve-hugging fit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • High waist seam
    • Side ruching, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4472

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life Made Easy Linen Halter Maxi Dress

    Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals. 

    Fit & Features

    • Sleeveless, halter v-neck, tie-closure
    • Partial open-back with tie
    • Hidden side pockets
    • Flowy silhouette
    • Front high-cut slit
    • Maxi-length hem
    • Striped linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4468

    Category Name: Casual Dresses

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Wild Leopard Mini Dress

    Flaunt your wild side in a leopard mesh mini dress for your next prowl! It features a sleeveless, square neck bodice with spaghetti straps and side ruched seams on a bodycon silhouette. Complete the look in heels.

    Fit & Features

    • Sleeveless bodice, square neck
    • Spaghetti straps
    • Side ruched seams
    • Mini-length bodycon silhouette
    • Leopard print pattern
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4470

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Summer Halter Maxi Dress

    Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • O-ring inset, cutout accent
    • Bodycon silhouette
    • Asymmetrical slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4467

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot Me In Leopard Slit Midi Dress

    You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

    Fit & Features

    • Sleeveless V-neckline, tank shoulder straps
    • Form-hugging, slim silhouette
    • Front slit
    • Midi-length flowy hem
    • Leopard print
    • Woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 05102-4469

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Like It's Hot Halter Midi Dress

    It's vacay season and this halter midi dress is here for it! Featuring a sleeveless, high neckline with a tie closure, cutout bodice with a cinch accent, and a bodycon midi-length hem. Composed of a nylon-blend knit fabric with a moderate stretch. Finish the look with trendy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, high halter neckline, tie closure
    • Cutout bodice, cinch accent
    • Bodycon silhouette
    • Midi-length hem
    • Nylon-blend knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1305

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovely In Floral Cowl Mini Dress

    You'll look lovely in this floral mini dress featuring a sleeveless, cowl neck, bungee spaghetti straps, and form-fitting silhouette on woven fabric with an inner knit lining. Complete the look in sleek wedges.

    Fit & Features

    • Sleeveless, cowl neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Mini-length hem
    • Floral print
    • Woven fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1576

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep Knit Chill Color Block Mini Dress

    Keep your look chill for a coffee run or casual hang in this color block mini dress.  Featuring short sleeves, a collared neckline, a button-down front, and a bodycon silhouette on stretchy, rib-knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Short sleeves
    • Collared neckline
    • Button-down front
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4466

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playful Floral Mesh Mini Dress

    Feeling playful? Brighten up your closet in this floral mesh mini dress perfect for brunch with the girls! It features a sleeveless, v-neck, adjustable spaghetti straps, a bodycon silhouette, center, and sides ruched seams to highlight your curves. Complete the look in lucite heels.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Center and side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern, back zipper closure
    • Mesh-lined fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4461

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jungle Cat Leopard Cowl Midi Dress

    You're the queen of the jungle in this leopard midi dress featuring a sleeveless, cowl neck, spaghetti straps, slim-fit silhouette, and a sultry front slit. Complete the look in heels.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Slim-fit silhouette
    • Midi-length hem
    • Front slit accent
    • Leopard print
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed And Fab Floral Skater Dress

    Bring the charm with a skater dress that creates a fab moment! The dress features a floral print, a sleeveless wrap V-neckline, adjustable spaghetti straps, and an elastic drawstring at the waist. The waist leads to a flowy skater skirt with a tiered ruffled design. Complete look with wedges and butterfly clips. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Adjustable spaghetti straps
    • Elastic drawstring at waist
    • Floral print
    • Tiered ruffles
    • Short length skater hem 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05101-1575

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Palisades Ruched V-Neck Midi Dress

    Let the sun kiss your shoulders in this flowy midi dress! It features a sleeveless ruched v-neck and spaghetti straps that lead to the sultry open-back with a lace-up closure. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, ruched v-neck, spaghetti straps
    • Flowy midi-length silhouette
    • Open-back, lace-up closure
    • Gauze woven fabric
    • Inner lining
    • Fits true to size

    Style Number/Barcode: 05102-4456

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take A Bow Ruffled Short Dress

    Flaunt your flirty self and bow in this short dress featuring a sleeveless, square neck, adjustable spaghetti straps, a partial open-back with bow-tie closure, and a tiered ruffle hem. Complete the look in a choker necklace and mules. 

    Fit & Features

    • Sleeveless, square neck
    • Adjustable spaghetti straps
    • Partial open-back, bow-tie closure
    • Tiered ruffles
    • Short-length hem
    • Fits true to size

    Style Number/Barcode: 05102-4457

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mystic Swirls Square Neck Mini Dress

    Create a sultry-mystic vibe for the night in this square neck dress featuring sleek spaghetti straps and a bodycon silhouette with backside ruching that accentuates every curve on the mesh-lined fabric. Complete the look in lucite mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ruched back detailing
    • Marble swirl pattern
    • Mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4453

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Farmer's Market Gingham Plaid Dress

    Head to the farmer's market looking so cute in this gingham plaid mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, and a bodycon silhouette with a front slit accent. Complete the look in a crop sweater and booties.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Gingham plaid pattern
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4452

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Trend Marble Ruched Short Dress

    Stay on trend with a short dress that creates a head-turning moment! The dress features a fab marble print, a sleeveless square neckline, spaghetti straps, ruching, and a short-length hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a cropped denim jacket. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Marble print
    • Ruching down the sides
    • Mini-length hem 
    • Lined smooth knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4455

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Knit High Slit Midi Dress

    This elevated brushed knit midi dress will be your new go-to for a casual night out. It features a sleeveless square neckline, spaghetti straps, an alluring center cutout at the waist, a midi-length, curve-hugging fit, and a thigh-high side slit. Style with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Center cutout at the waist
    • Midi-length, form-fitting silhouette
    • High side slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4451

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale