Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute outing, these casual dresses are built to move with your mood—and your calendar.

Show filters

Sort:

Size

Color

Price

All filters

Sort

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

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!

Flirty Frills Lace Romper
Flirt mode: on. This strapless lace romper is the perfect mix of sweet and sultry, finished with a ruffled hem that’s made for twirling through fall nights or layering under a blazer for date night.

Fit & Features
- Lace fabric, knit shorts lining
- Strapless neckline with bow
- Form-hugging bodice
- Layered ruffled skirt overlay
- Runs true to size
Style Number/Barcode: 06503-000165

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: BROWN

Available Size: S, M, L
Beauty So Effortless V-Neck Slit Maxi Dress
Envoke an effortless beauty by slipping into this maxi dress perfect for cocktail hour and dressy dinner dates! The dress features a sleeveless V-neck, dual spaghetti straps that format the caged low-back design, side ruched seams to accentuate your curves, a slim and curve-hugging fit, and a sultry high side slit and long hem. Complete the look with a glitter clutch and heels.

Fit & Features
- Sleeveless V-neck, dual spaghetti straps
- Caged low-back design
- Side ruched seams
- Slim and curve-hugging fit
- High-side slit, maxi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2407

Category Name: Casual Dresses

Price: $5.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Curves Ahead Sleeveless Ruched Midi Dress
Showcase curves in a ruched midi dress that elevates your night-out look! The dress features a sleeveless mock neckline, a ruched body, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit and a moderate stretch. Complete the look with clear mules.

Fit & Features
- Sleeveless mock neckline
- Ruched body
- Midi-length silhouette
- Smooth knit fabric, knit lining
- Form-hugging fit
- Moderate stretch
- Style runs small
Style Number/Barcode: 05101-0956

Category Name: Casual Dresses

Price: $6.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ocean Eyes Halter Maxi Dress
Serving sultry mermaid vibes, this maxi dress is pure liquid allure. With its daring plunge, bold hardware detail, and sleek fit, it’s the statement dress that makes every entrance unforgettable.

Fit & Features
- Abstract tie-dye print, mesh-lined stretchy fabric
- Plunge halter cowl neckline with hardware insert
- Open back with tie closure
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000674

Category Name: Casual Dresses

Price: $49.90

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, M, L
Garden Glam Floral Maxi Dress
This isn’t your garden-variety maxi dress, floral abstract print meets daring cutouts and sleek hardware trim for a look that’s equal parts sultry and statement. Perfect for casual celebrations, destination nights, or when you’re ready to own the room.

Fit & Features
- Floral Abstract print, mesh-lined stretch fabric
- Strapless sweetheart neckline, hardware trim
- Cutout bodice
- Side ruched seams
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000209

Category Name: Casual Dresses

Price: $42.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Laced Up Romance Halter Romper
Sweet but with a little spice—this lace romper stuns with a plunging V neckline, open tie back, and playful ruffle trim. Perfect for lunch dates, garden parties, or just stealing the spotlight.

Fit & Features
- Sheer lace fabrication with lining
- Halter V-neckline
- Open tie back detail
- Ruffled layered short hem
- Shorts lining
- Runs true to size
Style Number/Barcode: 06503-000170

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Hot Glow Denim Western Mini Dress
Bold lines, bold moves. This strapless bodycon mini dress features standout topstitch detailing and a daring front cutout that sculpts your curves and keeps all eyes on you.

Fit & Features
- Denim fabric, slight stretch, Western flame stitched design
- Strapless sweetheart wired neckline, padded bra cups
- Front keyhole cutout
- Back zipper and hidden button-up closures
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000181

Category Name: Casual Dresses

Price: $54.90

Availability: In Stock

Available Color: BLACK, DENIM

Available Size: XS, S, M, L
Deep Drama Long Sleeve Bodycon Dress
Bold meets sleek—this bodycon mini dress serves up long-sleeve polish with a curve-hugging ruched fit. Perfect for brunch, date nights, or any occasion when you want to look unforgettable!

Fit & Features
- Smooth knit stretch fabric
- Fitted long sleeves
- Plunge V-neckline
- Ruched bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000295

Category Name: Casual Dresses

Price: $45.90

Availability: In Stock

Available Color: OLIVE

Available Size: XS, S, L, XL
Into the Wild Leopard Maxi Dress
Wild but make it chic—this mesh maxi dress drapes effortlessly with a sheer animal print finish. The sleek straps and body-skimming silhouette make it perfect for layering or styling with heels.

Fit & Features
- Leopard print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000407

Category Name: Casual Dresses

Price: $49.90

Availability: In Stock

Available Color: TAUPE

Available Size: XS, S, M, L
Untamed Nights Zebra Print Maxi Dress
Go full wild mode in this zebra mesh dress—plunging cowl neckline, open back with tie straps, and a daring thigh-high slit. The hardware trim at the waist adds just the right amount of edge for a dress that owns every room.

Fit & Features
- Zebra print, mesh fabric, stretch knit lining
- Plunge halter cowl neckline
- Open back with ties
- Hardware waist trim
- High front slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000292

Category Name: Casual Dresses

Price: $46.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
In the Moment Bodycon Midi Dress
Sleek, sultry, and ready to steal the spotlight—this bodycon midi dress hugs in all the right places. The twist bust detail and V-neckline keep it flirty while the long sleeves add chic flair.

Fit & Features
- Smooth, double-lined knit stretch fabric
- Fitted long sleeves
- V-neckline with a twist bust
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000307

Category Name: Casual Dresses

Price: $45.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L, XL
Bold Exit Backless Midi Dress
For the girl who loves leaving them speechless. This open-back midi dress brings the drama without saying a word. Bonus points if you don’t look back.

Fit & Features
- Rib knit stretchy fabric, double-lined
- Fitted long sleeves
- Crew neck
- Cutout back
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000317

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Edgy In Plaid Scoop Neck Mesh Mini Dress
Show your edge in this plaid mesh mini dress featuring a flattering scoop neckline and form-hugging fit with a hanky-style hem. Complete the look with a cardigan.

Fit & Features
- Plaid print, mesh fabric, stretchy knit lining
- Spaghetti straps
- Scoop neckline
- Form-hugging fit
- Hanky-style mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5952

Category Name: Casual Dresses

Price: $26.90

Availability: In Stock

Available Color: BURGUNDY

Available Size: XS, S, M, L
Cute Agenda Long Sleeve Mini Dress
For the girl with a busy social calendar—this long sleeve mini dress is polished yet practical, featuring a sleek turtleneck, flattering knotted design, and a body-hugging fit that takes you from latte runs to casual dinners downtown.

Fit & Features
- Smooth knit-lined stretch fabric
- Fitted long sleeves
- Turtle neckline
- Front knotted design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000285

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Wild Thing Mesh Belted Strap Mini Dress
Equal parts fierce and flirty, this mesh mini dress brings major attitude with western-inspired belted straps and a ruffled hem that keeps it playful. The mesh scoop neckline and ruched sides seal the deal.

Fit & Features
- Mesh fabric lined with stretch knit
- Scoop neckline
- Back zipper and hook-eye closure
- Faux leather Western-inspired belted shoulder straps
- Side ruched seams, form-hugging bodice
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000225

Category Name: Casual Dresses

Price: $42.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Lovely Nights Strapless Lace Ruffle Skater Dress
Have a lovely night in this strapless lace dress boasting a flattering skater silhouette adorned with flirty ruffles perfect for dancing! Pair with a necklace.

Fit & Features
- Lace fabric, stretch knit lining
- Strapless neckline
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3813

Category Name: Casual Dresses

Price: $42.90

Availability: In Stock

Available Color: PINK, BLACK

Available Size: XS, S, L, M
Product Badge:
- Best Seller
Just Add Plans Strapless Skater Dress
Effortlessly cute, always ready for fun. This strapless skater dress pairs a sleek fit with a pleated mini hem that’s made for twirling into your next big moment.

Fit & Features
- Smooth ponte fabric, knit lining
- Strapless neckline
- Skater silhouette
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000412

Category Name: Casual Dresses

Price: $49.90

Availability: In Stock

Available Color: BLACK, WINE

Available Size: XS, S, M, L
Through The Meadow Floral Corset Dress
Too sweet to scroll past. This corset floral dress brings all the cottagecore charm with a flirty twist—yes, that oversized bow is doing the most. Perfect for shower celebrations or dressy events!

Fit & Features
- Floral print, woven texture fabric, lace trim woven lining
- Sweetheart lace trim neckline, bust tie
- Adjustable shoulder straps
- Corset bodice, flexible boning inserts, lace trim
- Back bow tie, zipper and hook-eye closure
- Drop waist seam, skater short-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000269

Category Name: Casual Dresses

Price: $62.90

Availability: In Stock

Available Color: WHITE

Available Size: S, M, L
Studded Rodeo Denim Mini Dress
Cowgirl meets cool-girl—this strapless denim mini dress unveils an edgy side with studded designs that bring just the right amount of cute to your Western vibe. Perfect for bachelorettes, concerts, or a night at the country bar.

Fit & Features
- Denim fabric
- Strapless neckline
- Back zipper closure
- Front studded trim design
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000231

Category Name: Casual Dresses

Price: $44.90

Availability: In Stock

Available Color: DENIM

Available Size: XS, S, M, L
Product Badge:
Wildflower Energy Cowl Halter Romper
This sheer mesh halter romper mixes floral and animal vibes for a look that’s flirty, fierce, and ready for your next night out!

Fit & Features
- Floral and leopard mix print, mesh-lined fabric
- Halter cowl neckline, spaghetti strap tie
- Open strappy back
- Built-in mini shorts with flirty skirt overlay
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06503-000082

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: LEOPARD

Available Size: XS, S, M, L
Product Badge:
- Back In Stock
Ruffle Repeat Lace Tube Mini Dress
She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.

Fit & Features
- Lace fabric, stretchy knit lining
- Strapless tube neckline
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000171

Category Name: Casual Dresses

Price: $48.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Chic Cutie Ribbed Knit Halter Midi Dress
Show up to happy hour looking like a chic cutie in this halter midi dress designed with hacci ribbed knit fabric for plenty of stretch. The tie-back halter straps lead to an alluring open back, while the curve-hugging fit flaunts your gorgeous figure.

Fit & Features
- Hacci ribbed knit fabric, high stretch, sewn-in knit lining
- Sleeveless V-neckline
- Tie-back halter straps
- Open back, lower ruched seam
- Midi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000149

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: IVORY, BURGUNDY, BLACK, MOCHA, OLIVE

Available Size: XS, S, M, L
Cozy Flirt Striped Mini Dress
Cozy yet flirty—this striped sweater mini dress hugs your curves with a snug knit and a sultry off-shoulder neckline. Pair it with boots or heels for the perfect fall night-out look.

Fit & Features
- Striped pattern, stretch knit fabric
- Folded off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000119

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: TAUPE

Available Size: XS, S, M, L
Fall Into Bloom Floral Maxi Dress
Romantic drama, unlocked—this floral maxi dress hugs in all the right places before flowing into a dreamy silhouette. With strappy back details and bold blooms, it’s perfect for autumn weddings, cocktail nights, or a dressy birthday event.

Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up strappy open back
- Curve-hugging silhouette
- Floor-length hem
- Runs true to size
Style Number/Barcode: 05101-000633

Category Name: Casual Dresses

Price: $44.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L, XL

Reset Your Password

Email Sent

Order Status

Casual Dresses

HomeCasual Dresses

Product Recommendations