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.

  • Casual Vibes Only Ribbed Knit Mini Dress

    Rock a basic ribbed mini dress for your everyday looks! The dress features a sleeveless square neckline, bungee straps, and composed of a ribbed knit fabric. Complete look with chunky sneakers for that casual vibe. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps 
    • Ribbed knit fabric 
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06002-0638

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Mood Ribbed Knit Midi Dress

    Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Open back 
    • Tie-back accent
    • Midi-length, high side slit
    • Lined ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4526

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Move It To The Music Mini Dress

    Move it and groove it to the music in this sassy mini dress featuring a sleek, sleeveless, v-neck, spaghetti straps, open-back with lace-up detail, form-fitting silhouette, and a swirl print woven fabric. Complete the look in platform lucite heels.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Open-back, lace-up detail
    • Form-fitting
    • Mini-length hem
    • Swirl print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4522

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Energy Marble Mesh Dress

    Radiate major stylish energy in this marble print mini dress featuring a sleek, sleeveless square neck with bungee spaghetti straps, a bodycon silhouette, and a sheer mesh overlay with lining. Complete the look braid strap mules.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Sheer mesh overlay, lining
    • Fits true to size

    Style Number/Barcode: 05102-4523

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Highly Sophisticated Sweater Dress

    This sleeveless sweater dress brings sultry-sophistication to every occasion! It features a halter neckline, side cutouts on the bodice, and a form-fitting silhouette on a mini-length hem. Complete the look in a classy blazer and heels.

    Fit & Features

    • Sleeveless, halter neckline
    • Side cutouts
    • Form-fitting silhouette
    • Mini-length hem
    • Soft sweater knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1377

    Category Name: Casual Dresses

    Price: $3.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Rose Tie-Back Ruffle Dress

    Sweet for the summer! Heads will turn when they see you in this rose print mini dress featuring a sleeveless square neck, spaghetti straps, high-waist seam, open-back with tie closure, and a surplice ruffled trim skirt. Complete the look with cork heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Open-back with tie closure
    • Surplice ruffled trim
    • Short-length hem
    • Rose print, lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1609

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lush Paradise Lace-Up Mini Dress

    Escape to a lush paradise in this tropical mini dress perf for your next island vacay! Featuring a sleeveless, square neck, spaghetti straps that lead to the open-back with a lace-up design, a bodycon silhouette, and palm print knit-lined fabric. Complete the look in sunglasses and heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up design
    • Bodycon silhouette
    • Mini-length hem
    • Palm print, stretchy knit-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4516

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Marble Print Mini Dress

    You'll look mesmerizing in this trendy-chic marble print mini dress! It features a sleeveless square neckline, spaghetti straps, a short, curve-hugging, bodycon silhouette, and an all-over marble print pattern. Style this dress with clear heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Marble print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4514

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marble Muse Mesh V-Neck Midi Dress

    Be your own muse! This marble mesh dress will become your new fave for cocktail soirees and evening dinner parties. It features a sleeveless, v-neck, adjustable criss-cross spaghetti straps, a bodycon silhouette, side ruched seam atop an asymmetrical hem. Complete the look with dangly earrings and heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Side ruched seam
    • Asymmetrical midi hem
    • Marble print, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4515

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Flower Lattice Back Dress

    Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lattice straps
    • Side slit, curve-hugging silhouette
    • Maxi-length hem
    • Tropical floral print, knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4506

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gimme Love Texture Knit Mini Dress

    Make em' fall for you in this curve-hugging mini dress featuring a sleek, sleeveless square neck, and bungee spaghetti straps, and is composed of texture-knit fabric with plenty of stretch. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Curve-hugging silhouette
    • Mini-length hem
    • Texture-knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4507

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Palms Strappy Midi Dress

    Enter paradise island in this sultry midi dress perfect for a dinner with a view! It features a sleeveless, square neck, spaghetti straps, high waist seam, and a strappy open-back, bodycon silhouette, side ruched seam, and slit along the hem. Complete the look in statement fringe earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam, strappy open-back
    • Bodycon silhouette
    • Side ruched seam and slit
    • Midi-length hem
    • Palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4508

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Glam Lattice Short Dress

    Bring it back to basics to make a glam impression in a short sweater dress that stuns! This must-have dress features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a lace-up back design, and a short-length hem. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross back 
    • Lace-up back 
    • Short-length hem 
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size 

    Style Number/Barcode: 06005-1332

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Party Paisley Knit Mini Dress

    This adorable paisley printed mini dress is perfect for all of your casual summer parties! It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, and a short, form-hugging fit. The brushed knit fabric offers plenty of stretch. Style this dress with cute mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, lace-up back design, tie closure
    • Mini-length, form-fitting silhouette
    • All-over paisley print pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4496

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miami Nights Bodycon Mini Dress

    Take on the night scene with your squad in this stunning printed mini dress. It features a sleeveless V-neckline, spaghetti straps, a dual twist-front design with waist cutouts for an alluring vibe, and a short, curve-hugging, bodycon silhouette. The stretchy knit fabric features an all-over geometric floral pattern. Complete your look with strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual twist-front design, waist cutouts
    • Mini-length, form-fitting silhouette
    • Geometric floral pattern
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4498

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready Set Vacay Gauze Maxi Dress

    Pack this flowy lightweight maxi dress in your carry-on as you jet set off on vacay! It features a sleeveless V-neckline, halter spaghetti straps, a smocked high waist with chic cutouts leading to an open strappy back, and a floor-length maxi silhouette with a side slit and a relaxed fit. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Smocked high waist, cutouts leading to open back
    • Strappy back design
    • Maxi-length silhouette, side slit
    • Woven gauze fabric, mini skirt knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4497

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Scene Crew Neck Midi Dress

    Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.

    Fit & Features

    • Crew neck, short sleeves
    • Cutout waist, knot accent
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Smooth cotton knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5765

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Hopping Tropical Maxi Dress

    Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.

    Fit & Features

    • Sleeveless, halter neck with tie
    • Cutout bodice
    • Open-back, tie closure
    • Side slit
    • Flowy maxi silhouette
    • Tropical print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4500

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Vacay Sleeveless Maxi Dress

    Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neck and back design
    • Tank shoulder straps
    • High-rise banded waist, side cutouts
    • Maxi-length hem, flowy silhouette
    • Front slit
    • Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4504

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Under The Palms Halter Skater Dress

    Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Side cutouts, strappy banded back design, tie closure
    • Smocked high waist, flowy skater skirt
    • Tropical palm leaf print
    • Gauze fabric, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4499

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Weekend Vibes Mini Dress

    This sleek satin floral dress is perfect for your weekend outings! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back lace-up design, and a mini-length, A-line silhouette. The lightweight satin fabric features an all-over dainty floral print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back lace-up design, tie closure
    • Mini-length, A-line silhouette
    • Dainty floral print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4494

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Floral Chiffon Dress

    Sashay and sway in this adorable floral chiffon dress featuring a sleeveless, scoop neck, adjustable spaghetti straps, smocked back panel, and a flowy, ruffled tiered short hem. Complete the look in trendy sandals for your next getaway.

    Fit & Features

    • Sleeveless, scoop neck, adjustable spaghetti straps
    • Smocked back panel
    • Flowy, tiered short hem
    • Floral pattern
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4495

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless, square neck, spaghetti straps that lead to an open-back with lace-up closure, a form-fitting silhouette, and a side slit atop the midi-length hem. Complete the look in sunglasses.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up closure
    • Form-fitting silhouette
    • Slit midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1317

    Category Name: Casual Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • It-Girl Status Midi Dress

    Showcase major it-girl status in this chic lace-up midi dress. It features a sleeveless scoop neckline, tank shoulder straps, an open back with a cross-back lace-up strappy design, a midi-length hem, and a curve-hugging silhouette. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Midi-length hem
    • Form-fitting, bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4489

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free