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.

  • Golden Hour Floral Ruffled Skater Dress

    Snap a dreamy pic for golden hour in this floral skater dress and watch the likes come through! It features an off-the-shoulder, sweetheart neckline with ruffle trim, peasant long sleeves, a smocked bodice with a front adjustable drawstring, a cutout waist, and a flowy tiered ruffled short-length hem. Complete the look in chic clear strap mules.

    Fit & Features

    • Off-the-shoulder, sweetheart neck, ruffle trim
    • Peasant long sleeves
    • Smocked bodice, front adjustable drawstring
    • Cutout waist, skater silhouette
    • Tiered ruffle short hem
    • Watercolor floral print, non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05101-1987

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alluring Marble Mesh Bodycon Dress

    This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.

    Fit & Features

    • Square neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Marble swirl pattern
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4863

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sent You A Text Square Neck Mini Dress

    You might want to reply back to your new favorite casual mini dress for weekend outings or day dates! It features a sleeveless square neck, tank-style straps, and a bodycon silhouette, and is composed of a textured fabric with a stretch knit lining. Style with a denim jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Tank-style straps
    • Bodycon silhouette
    • Mini-length hem
    • Textured fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4860

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Good Turtleneck Maxi Dress

    Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.

    Fit & Features

    • Long fitted sleeves
    • Turtleneck
    • Form-hugging silhouette
    • Side slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4861

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Stroll Ditsy Floral Midi Dress

    Take a springtime stroll in this adorable ditsy floral midi dress! Featuring a square neckline, short puff sleeves, a midi-length hem with a front slit, and a flowy A-line silhouette, this dress is perfect for weekend plans. The ditsy floral printed woven fabric includes a short knit lining. Style with sandals for a date with your special someone.

    Fit & Features

    • Square neckline
    • Short puff sleeves, elastic cinched hems
    • Smocked back panel, hidden side zipper
    • Midi-length hem, front slit, A-line silhouette
    • Ditsy floral print
    • Woven fabric, short knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1985

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Live Or Ride Graphic Short Dress

    Live life comfortably or on the edge! Showcase your wild lifestyle in this graphic short dress featuring short sleeves, a crew neck, a front script that reads, "Live Or Ride Legend" and a bustier-style bodice with mesh inserts and a fitted hem. Complete the look in combat boots.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Graphic front with a script, "Live Or Ride Legend"
    • Bustier-style bodice with mesh inserts
    • Fitted, short-length hem
    • Smooth and stretchy cotton fabric
    • Fits true to size

    Style Number/Barcode: 06002-1449

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On A Roll Turtleneck Midi Dress

    The styling possibilities are endless with this turtleneck midi dress! It features long sleeves, a bodycon silhouette, and a sultry side slit on stretchy rib-knit fabric. Complete the look in suede booties for the perf autumn outfit!

    Fit & Features

    • Long sleeves
    • Turtleneck
    • Bodycon silhouette
    • Side slit
    • Midi-length 
    • Rib-knit, lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4855

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Charm Ditsy Floral Skater Dress

    Show off your cute charm in this adorable ditsy floral skater dress! It features a square neckline with a ruffled trim, a ruched bust with a tie-front detail, short puff sleeves, a fitted high waist seam, and a short flared-out skater skirt with a flowy silhouette. The lightweight woven fabric features a dainty ditsy floral print pattern. Style with espadrille sandals for a picnic date.

    Fit & Features

    • Square neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elastic cinched hems
    • Back zipper, hook and eye closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Ditsy floral print, woven fabric, bust knit lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4854

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Midi Long Sleeve Slit Dress

    You can't be disturbed cause you'll be busy admiring yourself in this rib knit midi dress featuring long sleeves, a sweetheart neckline, bust seam detail, and a form-hugging silhouette with a sultry side slit. Complete your cute look in faux suede booties for a Friendsgiving! 

    Fit & Features

    • Long sleeves
    • Sweetheart neck
    • Bust seam detail
    • Form-hugging silhouette
    • Midi-length hem, side slit
    • Ribbed knit fabric, partial lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4853

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • For The Frill Ruffled Tie-Back Skater Dress

    You'll totally be eyeing this skater dress for its frills! Have your twirl-worthy moment in this short dress featuring a square neck, short puff sleeves, a tie-back detail, and a flowy fit and flare silhouette with a tiered ruffle trim skirt. Complete the look with a trendy purse and mules for a baby shower or celebration!

    Fit & Features

    • Square neck, short puff sleeves
    • Tie-back detail
    • Flowy, fit and flare silhouette
    • Tiered ruffle trim skirt
    • Short-length hem
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4851

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Chic Mock Neck Sweater Dress

    This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.

    Fit & Features

    • Ribbed mock neckline
    • Long fitted sleeves
    • Mini-length hem, front slit
    • Curve-hugging silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1616

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Doesn't Get Better Knit Midi Dress

    It doesn't get better than having this knit midi dress in your rotation! The dress features a trendy one-shoulder crew neckline with a long sleeve, spaghetti strap, and cutout bust that leads to the form-hugging silhouette with a sultry side slit hem. Complete the look in chic marabou heels.

    Fit & Features 

    • One-shoulder crew neckline
    • Long sleeve, spaghetti strap
    • Cutout bust
    • Form-hugging silhouette
    • Side slit hem, midi-length 
    • Smooth knit double-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4850

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walk The Line Crepe Geo Mini Dress

    Walk the line into this artsy geometric print crepe dress to give your closet must needed prints! It features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a flirty slit along the mini-length hem. Complete the look in heeled sandals for a casual brunch downtown!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Geometric print
    • Stretchy crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-4849

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple Chic Style Satin Mini Dress

    The simple chic style of this satin mini dress is perf for the babe who loves a classic look. It features a sleeveless V-neckline, bungee spaghetti straps, a fitted A-line silhouette, and a mini-length hem with an alluring front slit. The lightweight satin-knit fabric offers a moderate stretch. Complete the outfit with strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Fitted A-line silhouette
    • Mini-length hem
    • Front slit
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1965

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Scoop Neck Midi Dress

    You'll be wearing this midi dress on repeat! It features long sleeves, a scoop neck, and a bodycon silhouette with a sultry side slit. The dress is composed of a stretchy rib-knit fabric. Style with pointed-toe booties to complete your cute look!

    Fit & Features

    • Long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4846

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For You Marble Mesh Mini Dress

    This eye-catching marble mesh mini dress was made for you to style up and create a chic 'fit! It features a crew neckline, sheer long fitted sleeves, a mini-length hem, a bodycon silhouette that will hug your curves, and an all-over alluring marble print pattern. The partially lined mesh fabric offers plenty of stretch. Complete your look with strappy stilettos.

    Fit & Features

    • Crew neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4847

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You're The One Tie-Front Midi Dress

    This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!

    Fit & Features

    • Long sleeves
    • Surplice v-neckline
    • Faux wrap bust
    • Cutout bodice, tie-front closure
    • Bodycon, midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4843

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Everyday Style Midi Dress

    This form-fitting midi dress is perfect for creating that chic everyday style! It features a sleeveless V-neckline with a matching V-back design, tank shoulder straps, a fitted silhouette that will hug your curves, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, V-back design
    • Tank shoulder straps
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4844

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Cable Knit Tie-Front Mini Dress

    Bring all the cozy vibes this season in this adorable cable knit mini dress! It features a V-neck and back with wrap designs, long balloon sleeves with tapered hems, a high waist with a tie-front accent, and a short, form-hugging fit. Style with knee-high boots.

    Fit & Features

    • V-neck and back, wrap design
    • Long balloon sleeves, tapered hems
    • High waist seam, tie-front
    • Mini-length hem, form-hugging fit
    • Cable knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4842

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Girl Sweater Midi Dress

    Breeze in looking like a chic contemporary girl in this sweater midi dress! It features an on-trend cold shoulder with adjustable halter spaghetti straps, fitted long sleeves, a bodycon silhouette, and a front-side slit accent. Complete the look with lace-up heels for a dinner date!

    Fit & Features

    • Cold shoulder
    • Adjustable halter spaghetti straps
    • Fitted long sleeves
    • Bodycon silhouette
    • Front side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1613

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Stunner Graphic T-Shirt Dress

    Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.

    Fit & Features

    • Crew neckline, notched design, safety pin detailing
    • Short sleeves
    • Mini-length hem, form-hugging fit
    • Motorcycle and eagle graphic
    • Script that reads, "American Motorcycles Road Lifestyle 1974"
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1445

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sight To See V-Neck Slip Dress

    You'll be a sight to see in this casual slip dress perfect for dinner and drinks with your bae! It features a sleeveless v-neck, bungee spaghetti straps, a curve-hugging silhouette, and a short-length hem.  Style with earrings and heels to complete the look!

    Fit & Features

    • Sleeveless v-neck
    • Bust lining
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Short-length hem
    • Texture knit design, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4840

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Head-Turning Chic Marble Print Midi Dress

    Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.

     Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Abstract marble print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4837

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale