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.

  • Summer Vacay Lace-Up Tropical Maxi Dress

    Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Cowl neckline
    • Spaghetti straps, lace up back
    • Form-hugging fit
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5743

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • In The Tropics Halter Lace Tropical Mini Dress

    Hit the tropics in this stylishly sultry tropical mini dress perfect for dinner and cocktails! Crafted from a tropical patterned lace fabric, this mini-length dress features a halter neckline with tie closure and a stunning bodycon silhouette to show off your curves. Complete the look in sandals and earrings!

    Fit & Features

    • Tropical patterned lace fabric, stretchy knit lining
    • Halter neckline, tie closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5796

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dream Twirl Tie Strap Pleated A-Line Mini Dress

    Twirl all day in this pleated A-line mini dress at casual parties or outings! Featuring a flattering square neckline and delicate spaghetti strap ties, this A-line silhouette dress offers a flattering style. The hidden hook and eye fasteners provide a seamless look, while the pleated mini-length hem adds a flirty touch. Complete the look in platform shoes and earrings!

    Fit & Features

    • Stretch woven fabrication
    • Spaghetti strap ties
    • Square neckline
    • Hidden front hook and eye fasteners
    • A-line pleated silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5737

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sensational Allure One-Shoulder Abstract Mini Dress

    Step out and cue all the compliments in this abstract mini dress at birthdays or events! Crafted from an airy mesh fabric with an abstract print, this mini dress features a one-shoulder neckline, a sheer long sleeve with a flared cuff inspiring a 70s vibe, and a bodycon silhouette. Complete the look with a statement hair bow accessory.

    Fit & Feaures

    • Abstract print, mesh fabric lined with stretchy knit
    • One-shoulder neckline
    • Sheer long sleeve with flared cuff
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5738

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Abstract Beauty Printed Slit Midi Dress

    Embrace your inner beauty in this abstract printed slit midi dress for any casual occasion! Featuring a flattering sleeveless square neckline perfect for layering, delicate spaghetti straps, and a bodycon fit, this dress flatters every figure. The front slit and midi-length hem add a touch of elegance, while the abstract print and mesh fabric create a unique style. Complete the look in mules and a cropped jacket.

    Fit & Features

    • Abstract print, stretchy mesh fabric, sewn-in knit lining
    • Spaghetti straps
    • Bodycon fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05102-5736

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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:
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  • Think Sunshine Long Sleeve Cutout Crochet Mini Dress

    Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Crochet fabric, sewn-in knit lining, slight stretch
    • Sheer flared long sleeves
    • V-neckline
    • Hoop insert, cutout waist and back
    • Tie-back design
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5732

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Beauty So Unique Lace-Up Floral Chiffon Maxi Dress

    Give off undeniable grace and beauty in this floral chiffon maxi dress on vacation or at parties! Featuring delicate adjustable spaghetti straps, a V-neckline, and a stunning lace-up back, this dress will accentuate your curves and create a flattering silhouette with a front slit and maxi-length hem. Complete the look in heeled sandals and earrings!

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • V-neckline
    • Lace-up back, zipper and hook-eye closure
    • Front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3389

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute Style Button Ruffled Striped Linen Skater Dress

    Catch everyone's attention with your cute style in this striped skater dress perfect for casual summer plans!  Made with striped linen fabric, this dress is perfect for any occasion. Featuring a scoop neckline with a bust tie and adjustable spaghetti straps, this dress is both stylish and comfortable. The button down front and ruffled trim add a fun touch, while the skater silhouette and short-length hem create a flattering look. Complete the look with hoop earrings and trendy sandals.

    Fit & Features

    • Striped print linen-blend fabric lined with woven, no stretch
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Button down front and ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5731

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dose Of Sweetness Bodycon Floral Mini Dress

    Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.

    Fit & Features

    • Ditsy floral print
    • Sheer eyelet knit fabric with knit lining, plenty of stretch
    • Adjustable spaghetti straps
    • Square neckline, dainty lace trim
    • Ruched bust with mini flower detail
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5730

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fun And Games Tie Strap Bodycon Floral Mini Dress

    This floral mini dress is here for fun and games this summer! Perfect for casual weekend fun, this dress features spaghetti strap ties, a sweetheart neckline, and all-over ruched seams that accentuate your curves along the bodycon fit. Complete the look with a trendy purse.

    Fit & Features

    • Floral ditsy print, brushed knit fabric
    • Spaghetti strap ties
    • Sweetheart neckline
    • Ruched bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5728

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breezy Look Ruffled Cutout Woven Maxi Dress

    Create a breezy-chic look with this woven maxi dress that will prove to be a summer staple! Designed with a lightweight woven fabric accented with ruffled trims, the long dress features a sleeveless square neckline with a keyhole cutout and tie-front detail, adjustable spaghetti straps for a customized fit, and dual cutouts at the stretchy smocked waist that lead to an open lower back. The tiered flowy A-line silhouette will give you an effortlessly pretty look. Style with strappy sandals.

    Fit & Features

    • Woven fabric, ruffled trims, short knit stretchy lining
    • Square neckline, keyhole cutout with tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Dual cutouts leading to open lower back
    • Tiered flowy A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5729

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fabulous Destination Tropical Cowl Neck Maxi Dress

    Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.

    Fit & Features

    • Tropical palm print, stretchy knit fabric
    • Cowl neckline
    • Low cowl back, spaghetti strap tie
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5727

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Modern Romance Sleeveless Lace-Up A-Line Midi Dress

    Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.

    Fit & Features

    • Texture woven fabrication with a woven lining
    • Sweetheart neckline, ruched bust, dainty lace trim
    • Adjustable straps
    • Lace-up waist, stretchy smocked back
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5722

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Best Feeling Scoop Neck Cutout A-Line Midi Dress

    There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.

    Fit & Features

    • Modal blend woven fabric with lining
    • Adjustable spaghetti straps
    • Scoop neckline
    • Stretchy smocked bodice with cutout
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5718

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Make Hearts Flutter Short Sleeve Cutout Maxi Dress

    You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Gauze woven fabric, short knit stretchy lining
    • Flutter short sleeves
    • Plunge V-neckline and V-cut back
    • Elasticized strappy waist with side cutouts
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5719

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • To Be Adored Scoop Neck Floral Lace Mini Dress

    You're certain to be adored in this floral lace mini dress wherever you go! The scoop neckline with a bust tie adds a touch of feminine charm while the adjustable spaghetti straps provide a perfect fit. Its bodycon silhouette and mini-length hem accentuate your curves, making you feel confident and stylish. Complete the look with a mini handbag.

    Fit & Features

    • Ditsy floral print, lace fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Scoop neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5717

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow Your Heart Sleeveless Ruffled Lace Maxi Dress

    Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3382

    Category Name: Casual Dresses

    Price: $28.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Talking Sweet One-Shoulder Cutout Eyelet Lace Dress

    Dress to impress in this sweet one-shoulder cutout eyelet lace dress guaranteed to turn heads as the lovely bride-to-be or graduate! Made from eyelet lace fabric, this bodycon dress will hug your curves in all the right places. This stunning mini-length dress features a trendy one-shoulder neckline, a flirty puff sleeve, and a sultry side drawstring cutout so you can customize the look. Style this dress with sandals and a tote bag.

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Drawstring side cut-out
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5715

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sure To Love Floral Woven Puff-Sleeve Skater Dress

    You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining
    • Ruched scoop neckline with tie-front detail
    • Short puff sleeves with elastic cinched hems
    • Stretchy smocked high waist
    • Fit-and-flare silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5716

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • True Devotion Strapless Ruffle Skater Mini Dress

    Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.

    Fit & Features

    • Cotton woven fabric with non-stretch lining
    • Strapless neckline with tie
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5711

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Bound Cutout Tropical Mesh Midi Dress

    You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.

    Fit & Features

    • Tropical palm leaf print
    • Mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Square neckline
    • Side cutout drawstring
    • Bodycon fit, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5710

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Special Stunner One-Shoulder Cutout Ombre Maxi Dress

    Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.

    Fit & Features

    • Ombre mesh fabric, stretchy knit lining
    • One-shoulder neckline, adjustable spaghetti strap
    • Side cutout
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5708

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Blis Sleeveless Bodycon Knit Midi Dress

    Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.

    Fit & Features

    • Unique knit fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline, bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5712

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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