Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

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Everyday Ease: Casual Dresses for Cool-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in burgundy or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • 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:
    • Sale
  • Feel The Romance Sweetheart Button Lace Trim Maxi Dress

    Instantly feel the romance of this sleeveless maxi dress for a chic and breezy look at showers or parties! It has a sweetheart neckline, adjustable straps, and a ruched bust, so it effortlessly highlights your figure. The button accents and sheer lace trims add delicate touches, while the high waist and flowy maxi silhouette create a flattering and ethereal look. Style this maxi dress with trendy sandals and earrings.

    Fit & Features

    • Airy woven fabric, short woven lining, no stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Button and sheer lace trim accents
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5706

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Style Tie-Back Bodycon Slit Zebra Midi Dress

    This sleeveless bodycon midi dress features a flattering scoop neckline and spaghetti straps that shape the tie-back design and a side slit. The stretchy knit material boasts a zebra print perfect for brunch or parties.

    Fit & Features

    • Stretchy knit material, zebra print, sewn-in knit lining
    • Scoop neckline
    • Spaghetti straps
    • Tie-back design
    • Side slit
    • Bodycon midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5830

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Nature Sleeveless Abstract Mesh Mini Dress

    A sleeveless mesh mini dress features a crew neckline and flattering side ruched seams to enhance your curves along the bodycon silhouette. The mesh fabric showcases an artsy abstract print for a unique look.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining, moderate stretch
    • Crew neckline
    • Side ruched seams
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5851

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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:
    • Sale
  • 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:
    • Ships Free
  • Follow The Sun Lace-Up Tropical Midi Dress

    Follow the sun to your next destination in this tropical midi dress! This bodycon dress flatters your figure with a square neckline, spaghetti straps, and a lace-up back. The side ruched seam and slit add a touch of chic to the midi-length hem. Complete the look in sunglasses and sandals!

    Fit & Features

    • Tropical print, stretchy knit fabric, bust lining
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5745

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ultimate Chic Choice Floral Tie-Back Short Dress

    For the ultimate chic choice, pick this floral short dress for all your summer plans! The sweetheart neckline and spaghetti straps give a flirty touch, while the dual tie-back design ensures a perfect fit. The underwire bust and flexible boning offer support and structure, with a short-length hem for a stunning silhouette. Complete the look with dainty chic earrings.

    Fit & Features

    • Ditsy floral print, woven fabric lined with stretchy knit
    • Sweetheart neckline, underwire bust
    • Spaghetti straps
    • Dual tie-back design
    • Flexible boning
    • Short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3447

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Watch Me Bloom Off-The-Shoulder Floral Midi Dress

    Be the talk of any garden party in this floral midi dress! The off-the-shoulder neckline exudes femininity, while the cutout waist shows some skin. The flowy midi-length silhouette and front slit offer a trendy allure. Complete the look in lace-up heels and earrings.

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Off-the-shoulder neckline
    • Cutout waist
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3414

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Attitude Strapless Bodycon Denim Mini Dress

    A strapless denim mini dress features a flattering bodycon silhouette with classic jean styling with pockets. Perfect for casual occasions.

    Fit & Features

    • Denim fabric, moderate stretch
    • Strapless neckline
    • Bodycon mini-length silhouette
    • Front button and zipper closure
    • Flap pockets
    • Runs true to size

    Style Number/Barcode: 05102-5854

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Into Fashion Crew Neck Open Back Maxi Dress

    You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Strappy open back
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5654

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can’t Resist Off-The-Shoulder Ruffle Mini Dress

    Soft, sultry, and a little playful—this off shoulder mini dress shows just the right amount. With ruched seams and a flirty ruffle hem, it’s your go-to for dates and weekend plans.

    Fit & Features

    • Soft stretchy double-lined knit fabric
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Side ruched seams
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000345

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Island Neutrals Halter Strappy Tropical Midi Dress

    Unveil this chic tropical midi dress on the island! The cowl halter neckline and strappy open back add a touch of allure, while the bodycon silhouette and asymmetrical cut hem flatter your figure. Complete the look with cute block heel sandals and sunglasses!

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Halter cowl neckline, spaghetti strap
    • Strappy open back
    • Bodycon fit
    • Asymmetrical cut hem
    • Runs true to size

    Style Number/Barcode: 05102-5185

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Babe V-Neck Halter Lace Trim Mini Dress

    Everyone will be asking about the effortless babe in this sleeveless mini dress! Featuring a halter V-neckline and delicate lace trim, this mini dress is sure to turn heads. The bust bow tie adds a playful touch while the bodycon fit flatters your figure. Complete the look with sandals for a sunny day out.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Halter V-neckline with lace trim
    • Bust bow tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5814

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Neutral Babe One-Shoulder Abstract Mini Dress

    A one-shoulder abstract mini dress features side ruched seams that accentuate your curves along the bodycon silhouette perfect for styling with heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • One-shoulder neckline
    • Side ruched seams
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5868

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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

    Product Badge:
    • Ships Free
  • Perfect Striped Halter V-Neck Mini Dress

    This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!

    Fit & Features

    • Striped print, mesh fabric, soft stretchy knit lining
    • Halter V-neckline
    • Open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5811

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Profound Bloom Off-The-Shoulder Floral Skater Dress

    You'll be blossoming from all the compliments you'll get wearing this off-the-shoulder floral dress! This skater dress features a playful sweetheart neckline, a bust tie, and a ruffled short-length hem bringing plenty of sass and sweetness to your style. Complete the look with earrings and strappy sandals for any occasion!

    Fit & Features

    • Floral print, woven fabric, bust lining
    • Off-the-shoulder, sweetheart neckline
    • Padded bra cups, back zipper and hook-eye closure
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3459

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Stunning One Halter V-Neck Ruffle Floral Maxi Dress

    You'll take every vacation or summer party by storm when you have this floral maxi dress! This stunning maxi dress features a halter V-neckline with spaghetti strap tassel ties, a stretchy smocked bodice accentuating your figure, and hidden side pockets for added convenience. The flowy ruffled silhouette and floor-length hem add a stylish finish. Complete the look in sandals and sunglasses!

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5776

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Trending Strapless Striped Bodycon Mini Dress

    Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals. 

    Fit & Features

    • Striped print, stretchy knit material
    • Strapless sweetheart twist neckline
    • Keyhole cutout
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5824

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picking Flowers Halter Strappy Back Daisy Skater Dress

    This daisy print skater dress will have you dreaming of sunny days picking flowers! The halter spaghetti strap neckline perfectly frames your shoulders while the cutout bodice adds a touch of allure. The strappy open back creates a stunning statement and the skater silhouette and tiered ruffled short-length hem give you a playful and fun look. Complete the look in sandals for a brunch or day date!

    Fit & Features

    • Daisy print, woven fabric with lining, no stretch
    • Spaghetti strap
    • Strappy open back
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5794

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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:
    • Sale
  • Sweeten The Occasion V-Neck Bow Lace Mini Dress

    No matter the occasion, you'll always look sweet in this lace mini dress! With its faux suede spaghetti straps and V-neckline trim adorned with a bow tie, this dress offers a bodycon fit and a mini-length hem for a flattering and stylish look. Complete the look in a crop denim jacket.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Faux suede spaghetti straps and V-neckline trim with bow
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5752

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale