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!

  • Alluring Accents Bodycon Mini Dress

    You'll love the alluring accents of this trendy-chic bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, a revealing side cutout at the waist, ruching down one side with an adjustable drawstring, and a short, curve-hugging fit. The smooth knit fabric features an all-over snake print pattern. Style this dress with clear heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side cutout at the waist
    • Ruching down one side, adjustable drawstring
    • Bodycon silhouette, mini hem
    • Snake print, lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4473

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feel The Heat V-Neck Midi Dress

    Sizzle and stun in this midi dress perf to bring up the temps! It features a sleeveless plunge V-neckline with a center O-ring insert, cutout bodice, form-fitting silhouette, and a side slit accent. Complete the look in lucite mules for a night out.

    Fit & Features

    • Sleeveless, plunge V-neck
    • Center O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Side slit accent, midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1448

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • One Love Sweetheart Sweater Dress

    The sweater dress your wardrobe needs! It features a sleeveless, sweetheart neckline, shoulder straps, a ruched bust seam, and a flirty cutout waist leading to the bodycon, mini-length silhouette. Complete the look in statement earrings.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, sweetheart neckline, shoulder straps
    • Ruched bust seam
    • Cutout waist
    • Bodycon silhouette
    • Mini-length hem
    • Hacci ribbed-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4751

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hardrock Babe Graphic Short Dress

    You're with the band. Enter backstage in this edgy babe-status graphic short dress featuring a strapless bodice, lace-up bungee straps, flexible boning inserts, side denim panels with seam detail, and a front script that reads, "Make Some Noise/ Hardrock" and a form-fitting short hem. Complete the look in a ring set.

    Fit & Features

    • Strapless tube bodice
    • Lace-up bungee straps, flexible boning inserts
    • Side denim panels, seam detail
    • A font script reads, "Make Some Noise/ Hardrock"
    • Form-fitting, short-length hem
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06002-1222

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take Me On A Getaway Midi Dress

    You'll be ready for a fab weekend getaway in this curve-hugging midi dress! It features a sleeveless sweetheart neckline with halter straps, chic waist cutouts, and a midi-length, form-fitting silhouette with a thigh-high side slit. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Waist cutouts
    • Midi-length, form-fitting silhouette, high side slit
    • Textured ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4687

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bae-cation Palm Print Mini Dress

    Look and feel like a total bae on vacay! This tropical mini dress is essential for exploring the island in style. It features a sleeveless, square neck, adjustable spaghetti straps, side ruched seams, and a brushed knit fabric offering a form-hugging fit and moderate stretch. Complete the look in espadrille wedges and earrings.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Mini-length hem
    • Palm print, brushed knit-lined fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4557

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Light Sweater Midi Dress

    Keep your look light and effortless in this sweater midi dress perfect for any day or night summer event! It features a sleeveless, v-neck, spaghetti straps, a bodycon silhouette, and a sultry front slit. Complete the look in strappy sandals. 

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1420

    Category Name: Casual Dresses

    Price: $16.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Drama Abstract Mesh Maxi Dress

    The kind of dress that makes an entrance before you even say hello. With an abstract print, sultry cutout back, and daring front slit, it’s made for statement moments only.

    Fit & Features

    • Abstract print, airy mesh fabric, partial knit lining
    • Strapless tube neckline
    • Cutout back
    • Front slit
    • Curve-hugging, maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000320

    Category Name: Casual Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

  • One Night Of Chic Mesh Maxi Dress

    Have your chic moment in this mesh maxi dress featuring a sultry, one-shoulder neckline, a partial open-back, side and back ruching, and an asymmetrical maxi-length hem with a side slit cutout. Complete your dressy look in sleek heels.

    Fit & Features

    • Sleeveless, one-shoulder neckline, spaghetti strap
    • Partial open-back
    • Side and back ruching
    • Side slit cutout
    • Asymmetrical maxi-length hem
    • Form-hugging fit, partial lining, mesh fabric
    • Fits true to size

    Style Number/Barcode: 05102-4736

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lush Paradise Lace-Up Mini Dress

    Escape to a lush paradise in this tropical mini dress perf for your next island vacay! Featuring a sleeveless, square neck, spaghetti straps that lead to the open-back with a lace-up design, a bodycon silhouette, and palm print knit-lined fabric. Complete the look in sunglasses and heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up design
    • Bodycon silhouette
    • Mini-length hem
    • Palm print, stretchy knit-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4516

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Palm Perfect Tropical Midi Dress

    Look perfect in paradise wearing this palm print midi dress featuring a sleeveless, v-neck, spaghetti straps, a form-fitting silhouette, and a front slit accent on stretchy knit fabric. Complete your vacation look in wedges.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Form-fitting silhouette
    • Front slit accent
    • Midi-length hem
    • Palm print, knit fabric with moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4542

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marble Muse Mesh V-Neck Midi Dress

    Be your own muse! This marble mesh dress will become your new fave for cocktail soirees and evening dinner parties. It features a sleeveless, v-neck, adjustable criss-cross spaghetti straps, a bodycon silhouette, side ruched seam atop an asymmetrical hem. Complete the look with dangly earrings and heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Side ruched seam
    • Asymmetrical midi hem
    • Marble print, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4515

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paisley Queen Ruched Mini Dress

    Enchant them all in your love for all things paisley! This square neck mini dress features a sleeveless bodice, spaghetti straps, a bodycon silhouette, and a front ruched seam on stretchy knit fabric. Complete the look in espadrille wedges.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Front ruched seam
    • Mini-length hem
    • Paisley print knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4650

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Timeless Twist One Shoulder Dress

    Bring the allure in this one-shoulder maxi dress featuring a sleeveless bodice, a single spaghetti strap, and a form-hugging silhouette atop an asymmetrical slit hem with a timeless twist accent. Complete the look in dangly earrings and heels.

    Fit & Features

    • Sleeveless, one-shoulder
    • Single spaghetti strap
    • Form-hugging silhouette
    • Twist accent and slit
    • Asymmetrical maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4714

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nothing But Sultry V-Neck Midi Dress

    You'll be nothing but sultry in this midi dress for a party! It features a sleeveless, v-neck, bungee spaghetti straps, cutout bodice, open-back with tie closure, form-fitting silhouette, and a side slit accent along the hem. Complete the look with a sparkly bracelet and heels.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Open-back, tie closure
    • Cutout bodice
    • Form-fitting
    • Side slit, midi-length hem
    • Slinky knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4724

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Summer Mood Knit Mini Dress

    This stretchy ribbed knit mini dress is perfect for those casual summer days. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing down the side seams with adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Style with cute slides.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Ruching down the side seams, adjustable drawstrings at the hem
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4685

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet For You Marble Mesh Mini Dress

    This mesh mini dress will look so good and so sweet in your lineup! It features a sleeveless square neckline, adjustable spaghetti straps, a short, curve-hugging, bodycon silhouette, and an all-over marble print on a lined mesh fabric. Complete your cool summer look with strappy heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Marble print
    • Sheer mesh fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4568

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Beauty Tropical Maxi Dress

    Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.

    Fit & Features

    • Sleeveless, square neck, halter straps
    • Open-back with tie
    • Bodycon silhouette
    • Front twist accent and slit
    • Maxi-length hem
    • Tropical palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4720

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Times Marble Halter Dress

    Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.

    Fit & Features

    • Halter neckline, ruched drawstring, tie closure
    • Cutout bodice
    • Form-hugging fit
    • Mini-length hem
    • Marble print knit-lined fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4531

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot And Cold Sweater Mini Dress

    Sweaters may be for cold weather but this mini dress is too hot not to be seen this summer! It features an off-the-shoulder neckline, short sleeve cuffs, a form-fitting silhouette, and a mini-length hem on stretchy rib-knit fabric. Complete the look in platform heels. 

    Shop More Sweater Styles: Shop The Collection

    Fit & Features

    • Off-the-shoulder neckline
    • Short sleeve cuffs
    • Form-fitting silhouette
    • Mini-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1423

    Category Name: Casual Dresses

    Price: $7.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Resort Ready Palm Print Mini Dress

    You'll be ready for your getaway at the resort with this tropical mini dress in your arsenal! It features a sleeveless square neck, sleek spaghetti straps, a palm print, and a curve-hugging silhouette. Complete your vacay look in espadrille wedges.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Curve-hugging silhouette
    • Mini-length hem
    • Palm print
    • Soft brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4681

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Tease Floral Tube Maxi Dress

    She’s sweet from afar—but up close? Full body-con bombshell. This floral maxi dress is made for occasions you don’t want to forget.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Tube neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000511

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L, XL

  • Summer Fridays Halter Midi Dress

    Bring the heat this summer in this sultry midi dress on a Friday night out! It features an off-the-shoulder, halter neckline, a cinched bust with cutout accents, a form-fitting silhouette, and a flirty side slit. Complete the look in strappy mules.

    Fit & Features

    • Off-the-shoulder, halter neckline
    • Cinched bust, cutout accents
    • Form-fitting silhouette
    • Side slit, midi hem
    • Texture knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4444

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Energy Marble Mesh Dress

    Radiate major stylish energy in this marble print mini dress featuring a sleek, sleeveless square neck with bungee spaghetti straps, a bodycon silhouette, and a sheer mesh overlay with lining. Complete the look braid strap mules.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Sheer mesh overlay, lining
    • Fits true to size

    Style Number/Barcode: 05102-4523

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale