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.

  • Brunch Plans Cherry Halter Skater Dress

    Turn heads effortlessly in this adorable cherry mini dress for brunch or celebrations! Its flattering halter neckline and playful skater silhouette create a perfect balance of flirty and fun for your summer wardrobe.

    Fit & Features

    • Cherry embroidered pattern
    • Gauze cotton fabric, multiple woven and tulle linings
    • Plunge halter neckline, tie closure
    • Back zipper and hook-eye closure
    • Drop waist seam
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000175

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Belt It Babe Strapless Denim Mini Dress

    This denim tube dress understood the assignment—snatched waist, pleats for drama, and grommets for edge. The belted fit hugs you just right, and the mini hem? Major moment.

    Fit & Features

    • Denim fabric
    • Strapless tube neckline with grommet trim
    • Fitted bodice with seam detail
    • Adjustable belted waist
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000171

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tan Lines Cutout Bodycon Mini Dress

    Flaunt your figure in this sultry strapless mini dress on vacay or a bach weekend! Designed with cutout accents and stylish hoop inserts, it creates an alluring silhouette that demands attention along the bodycon silhouette.

    Fit & Features

    • Texture knit stretchy fabric, sewn-in knit lining
    • Strapless sweetheart neckline
    • Front cutouts and hoop inserts
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000170

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweetly Sultry Floral Bodycon Midi Dress

    So sweet and sultry in every way, this floral midi dress flaunts a sleek, flattering strapless neckline and bodycon fit perfect for shower celebrations or casual events.

    Fit & Features

    • Floral print, eyelet fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000169

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist Of Fate Strapless Ruffled Maxi Dress

    Because you didn’t plan to look this good... it just happened. Make your way in this breezy maxi dress designed with effortless, dreamy details from the twisted strapless bust to strappy open back and flowy ruffled silhouette. 

    Fit & Features

    • Satin woven fabric, woven lining
    • Strapless sweetheart neckline
    • Twisted bust, keyhole cutout accent
    • Strappy open back
    • Ruffled silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000168

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Curves Keyhole Maxi Dress

    Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.

    Fit & Features

    • Stretchy textured knit fabric
    • Scoop neckline with spaghetti straps
    • Front keyhole cutout at bust
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000166

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Plans Floral Eyelet Corset Skater Dress

    Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.

    Fit & Features

    • Floral eyelet woven fabric, tulle and knit linings
    • Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
    • Underwire bust support
    • Tie-shoulder straps, side zipper and hook-eye closure
    • Corset bodice with boning, V-shaped waist, ruffled trim
    • Lace-up back design, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000130

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Chic Sleeveless Midi Dress

    Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!

    Fit & Features

    • Woven fabric
    • Boat neckline
    • Low-cut back
    • Drop waist seam
    • Flowy silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000164

    Category Name: Casual Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girly Gingham Print Ruffled Mini Dress

    You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.

    Fit & Features

    • Smocked cotton fabric, high stretch
    • Gingham print
    • Sleeveless sweetheart neckline, ruffled trim, small bow detail
    • Adjustable spaghetti straps
    • Mini-length ruffled hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-000160

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Corset Cutie Denim Mini Dress

    From brunch dates to fun at the fair, she always eats. This skater denim mini dress serves flirty and fierce with a corset bodice and sweet bust tie that gives major retro babe energy.

    Fit & Features

    • Denim fabric, lace trim woven lining
    • Corset-style bodice with lace paneling, flexible boning
    • Sweetheart neckline, bust tie, lace trim, underwire bust
    • Adjustable lace trim shoulder straps
    • Back lace-up detail, zipper and hook-eye closure
    • Drop waist skater skirt with lace trim, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000157

    Category Name: Casual Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lowkey Head Turner Open Back Mini Dress

    She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.

    Fit & Features

    • Rib knit fabric, smooth, stretchy knit lining
    • Crew neck
    • Open back with tie detail
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000768

    Category Name: Casual Dresses

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: XS, S, M, L

  • Island Afterglow Knit Maxi Dress

    Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.

    Fit & Features

    • Texture knit fabric, smooth knit lining
    • Plunge V-neckline, hardware insert
    • Long bell sleeves
    • Cutout bodice, open back
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000155

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Summer Vibe Polka Dot Satin Mini Dress

    This polka dot satin mini dress will bring that sweet summer vibe featuring a dainty lace trim, halter V-neckline, and a short A-line silhouette. Style with sneakers for a casual look.

    Fit & Features

    • Satin woven fabric, sheer lace trim
    • Polka dot print
    • Sleeveless V-neckline
    • Halter straps with tie-back design, open back
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000156

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Cutie Halter Ruffle Mini Dress

    Make this halter mini dress a staple this season! The form-hugging silhouette accentuates your curves in all the right places, while the playful ruffled hem adds flirty movement. Style with strappy heels.

    Fit & Features

    • Texture knit fabric, moderate stretch
    • Cowl neckline
    • Spaghetti straps with hoop inserts
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000132

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Serve Abstract Print Mesh Bodycon Mini Dress

    Show off a sultry serve in this abstract print mesh mini dress designed with a strapless neckline and a bodycon fit to flaunt your curves.

    Fit & Features

    • Sheer mesh fabric, full-length knit lining, high stretch
    • Abstract print
    • Strapless straight-across neckline
    • Ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000133

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Sunny Days Crew Neck Poplin Midi Dress

    This sleeveless midi dress was made for romantic sunny days! It features a classic crew neck and a flattering drop waist seam that accentuates your figure along the A-line silhouette. 

    Fit & Features

    • Stretchy rib knit fabric, poplin woven fabric, stretchy knit lining
    • Crew neck
    • Drop waist seam
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000136

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Match My Energy Eyelet Skater Dress

    This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.

    Fit & Features

    • Eyelet fabric, sewn-in knit lining
    • Strapless neckline
    • Strappy back
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000108

    Category Name: Casual Dresses

    Price: $9.97 $65.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle Realness Denim Cutout Maxi Dress

    Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.

    Fit & Features

    • Denim fabric, sewn-in knit lining
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Cutout bodice design, hoop insert
    • Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
    • Ruffled tiered maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000131

    Category Name: Casual Dresses

    Price: $30.97 $68.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Allure A-Line Mini Tube Dress

    Show off a flirty allure in this adorable mini tube dress designed with a strapless straight neckline, drop waist, and a short, tiered, A-line silhouette. Style with sneakers for a cute and casual 'fit.

    Fit & Features

    • Lined knit fabric, high stretch
    • Elasticized strapless straight-across neckline
    • Ruched side seams
    • Drop waist design
    • Mini-length tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000130

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Boho Bell Sleeve Knit Mini Dress

    Live out those dreamy boho vibes in this breezy knit mini dress featuring a plunging V-neck with beaded bust tie accents, sheer long bell sleeves, and an open back with a tie-back design.

    Fit & Features

    • Sheer textured knit fabric, partial knit lining
    • Plunging V-neckline, dual bust ties with beaded detailing
    • Sheer long bell sleeves
    • Open back, tie-back spaghetti straps
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000129

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Sweet A-Line Mini Dress

    Proof that effortless can still be everything. This scoop neck mini dress hugs your curves with a sleek A-line fit—perfect for date night, birthday dinners, or dressy occasions!

    Fit & Features

    • Structured woven fabric, bust lining
    • Scoop neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-Line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000104

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale