Casual Dresses

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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.

  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Lace Off-The-Shoulder Drop Waist Romper

    Look like a daydream in this boho lace romper designed with a ruffled off-the-shoulder neckline and a flattering skater silhouette.

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Off-the-shoulder straight neckline, ruffled overlay
    • V-shaped drop waist
    • Flowy shorts, skater silhouette
    • Romper in size small is 25" shoulder to hem with an 8.5" front rise and a 3" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1228

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ahead Of The Curve Crew Neck Bodycon Mini Dress

    A sleeveless mini dress that's ahead of the curve in every way! With a flattering bodycon fit and a mini-length hem, this dress will accentuate your curves in all the right places. The crew neckline and side ruched seam add unique details to this stylish dress. Complete the look with a crop jacket and sandals for any plans!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Crew neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5753

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Strappy Back Maxi Dress

    A dress that does the flirting for you—sleek, slinky, and unforgettable. With a curve-loving fit and sultry strappy back, it’s your go-to for nights that demand a little drama.

    Fit & Features

    • Slinky knit fabric, high stretch
    • Sleeveless V-neckline
    • Dual bungee spaghetti straps
    • Open back, cross-back strappy design
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000368

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Day Dream Lace Up Eyelet Skater Dress

    Make your garden party daydream come true in this floral eyelet skater dress! This playful skater dress features a sweetheart neckline, spaghetti straps, and a lace-up back for a flirty touch. Its skater silhouette and short-length hem make it perfect for twirling! Complete the look with teardrop earrings and a bracelet.

    Fit & Features

    • Floral print, eyelet woven lined fabric, no stretch
    • Sweetheart neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3197

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Day Sleeveless Mermaid Denim Midi Dress

    Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Denim fabric, minimal stretch
    • Spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5567

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Design Cutout Bodycon Knit Midi Dress

    This bodycon midi dress features a sultry lower back cutout and back slit accent for a chic allure. The curve-hugging dress is made with a lined, soft, brushed knit fabric offering plenty of stretch for comfortable wear.

    Fit & Features

    • Lined brushed knit fabric, plenty of stretch
    • Square neckline
    • Tank shoulder straps
    • Lower back cutout
    • Back slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5595

    Category Name: Casual Dresses

    Price: $14.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemain Charm Halter Open Back Tie Dye Maxi Dress

    Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.

    Fit & Features

    • Tie dye print, stretchy mesh fabric, sewn-in knit lining
    • Halter cowl neckline
    • Open back with tie closure
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3445

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Charmer Ribbon Bow Bodycon Mini Dress

    Show off your cute charm in this bodycon mini dress on day dates or weekend brunch! Designed with a double-lined brushed knit fabric, this mini-length dress offers plenty of stretch for comfortable wear. It features a sleeveless square neckline with a dainty sheer eyelet lace trim and ribbon bow detail, spaghetti straps, and ruching down the side seams to accentuate your curves along the bodycon silhouette. Complete your coquette-inspired look with pearl earrings and strappy mules!

    Fit & Features

    • Stretchy double-lined brushed knit fabric
    • Square neckline
    • Sheer eyelet lace trim, ribbon bow detail
    • Spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5735

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Class Act Cowl Neck Polka Dot Midi Dress

    A sleeveless polka dot midi dress features a flattering cowl neckline, spaghetti straps, and a flowy silhouette with a front slit. Perfect for styling with stiletto heels for any occasion.

    Fit & Features

    • Polka dot print, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Cowl neckline
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5849

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine On My Mind Strapless Tropical Skater Dress

    This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical palm print, gauze woven fabric, bust lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5744

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made To Amaze Strapless Marble Bodycon Midi Dress

    Everyone will admire your style in this strapless marble bodycon midi dress at the art show downtown! Made from a mesh fabric boasting a gorgeous marble print, you'll be sure to amaze. With a strapless neckline and side ruched seams, this dress hugs your curves in all the right places for a bodycon fit along the midi-length hem. Complete the look with stiletto heels.

    Fit & Features

    • Marble print, stretchy mesh fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5576

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Must-Have Tie Back A-Line Mini Dress

    A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Open tie-back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5681

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce Flirt Animal Print Mini Dress

    This animal print mini dress was made for turning heads. With its draped cowl neckline, strappy halter fit, and flouncy layered hem, it’s a party dress with untamed vibes.

    Fit & Features

    • Animal print, mesh-lined stretchy fabric
    • Halter cowl neckline with adjustable belted strap
    • Open back
    • Form-hugging fit
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000320

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Plans Ribbed Knit Maxi Dress

    This casual-chic maxi dress is perfect for your upcoming weekend plans. It features a sleeveless one-shoulder neckline for an effortless and trendy vibe, a single tank shoulder strap, an open back with a dual strap design, a fitted, maxi-length silhouette, and a high side slit. Style this dress with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single tank shoulder strap
    • Open back, dual strap design
    • Maxi-length hem, form-hugging fit, side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4737

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Fab Sweater Dress

    You'll look so cute and fab in this trendy sleeveless sweater dress. It features a mock neckline, a short, curve-hugging fit, and is composed of a fuzzy eyelash knit fabric. Style this dress with combat booties.

    Fit & Features

    • Sleeveless
    • Ribbed mock neckline
    • Mini-length, form-fitting silhouette
    • Eyelash knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1112

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale