Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, 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 dinner date, these casual dresses are made to move with your mood—and your calendar.

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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!

Major Fling Flutter Sleeve Maxi Dress
Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.

Fit & Features
- Airy cotton fabric, woven lining
- Flutter short sleeves
- V-neckline
- Cutout back
- Ruffled tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000748

Category Name: Casual Dresses

Price: $54.90

Availability: Out of Stock
Product Badge:
- Ships Free
Playful Romance Floral Ruffle Mini Dress
Romantic, but still a little playful. This floral mesh halter mini dress features a plunging neckline and tiered ruffle hem with a sash detail that moves effortlessly from brunch plans to sunset drinks.

Fit & Features
- Floral print, mesh-lined stretchy fabric
- Plunge halter neckline with tie strap
- Open back design with tie strap
- A-line silhouette, ruffled trim detail
- Side ruffled drape
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001337

Category Name: Casual Dresses

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Attention Floral Tube Mini Dress
Booked the trip just to wear this dress. The bold tropical floral print and bodycon silhouette will make heads turn at the beach clubs, island resort, or a weekend pool party!

Fit & Features
- Statement floral print, knit-lined stretchy fabric
- Strapless tube neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000751

Category Name: Casual Dresses

Price: $36.90

Availability: In Stock

Available Color: YELLOW

Available Size: XS, S, M, L
Easy Escape Textured Stripe Halter Dress
Made for sunshine-filled plans and easy outfit decisions. This textured stripe dress features a smocked halter bodice and a softly flared skirt that creates beautiful movement with every step. Perfect for beach vacations, brunch dates, and warm-weather weekends that call for effortless style.

Fit & Features
- Texture striped knit fabric, partial knit lining
- Halter neckline with tie straps
- Open back
- Flowy silhouette with a ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000753

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, M, L
Sultry Edge Faux Suede Halter Mini Dress
Low-cut confidence, no apologies. This sultry faux suede halter mini dress hugs just right with a plunging cowl neck and open back that are both daring and effortless.

Fit & Features
- Faux suede fabric, moderate stretch
- Rhinestone and studded trim
- Sleeveless plunging cowl neckline
- Halter tie-back straps
- Open back, lower cross-back design
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000862

Category Name: Casual Dresses

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Meet Me In Maui Mesh Maxi Dress
Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.

Fit & Features
- Tropical print, lined mesh fabric with stretch
- Strapless neckline
- Bodycon silhouette
- Fitted maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000763

Category Name: Casual Dresses

Price: $44.90

Availability: In Stock

Available Color: PINK

Available Size: S, M, L
Game Day Crush LA Bodycon Mini Dress
Serving varsity vibes with zero effort required. This bodycon mini dress hugs in all the right places with a sporty crewneck design that’s made for stadium games and casual hangs.

Fit & Features
- Knit cotton fabric, high stretch, knit lining
- Striped crew neckline
- Striped short sleeves
- "Los Angeles" front embroidered script
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000771

Category Name: Casual Dresses

Price: $34.90

Availability: In Stock

Available Color: WHITE

Available Size: XS, S, M, L
West Coast Icon LA Bodycon Mini Dress
West coast icon, LA attitude. This bodycon mini dress hugs your shape with a soft, stretchy feel that moves with you from game day to spontaneous plans.

Fit & Features
- Ribbed cotton-blend knit fabric, high stretch, knit lining
- Sleeveless crew neckline, contrast trim
- Tank shoulder straps
- "Los Angeles" front embroidered script
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000772

Category Name: Casual Dresses

Price: $32.90

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, M, L
Sculpted Ease Ruched Midi Dress
The gathered texture gives this silhouette its sculpted appeal. This drop-waist midi dress features a ruched bodice and underwire bust insert that bring definition to the softly flared shape. The structured detailing adds polished impact without overwhelming the clean finish.

Fit & Features
- Cotton-blend knit stretch fabric
- Sewn-in knit bodice lining
- Ruched fitted strapless bodice, non-slip grip lining
- Underwire bust insert
- Drop waist seam, side slit accent, flowy midi-length hem
- Back zipper with hook-and-eye closure
- Runs true to size
Style Number/Barcode: 05102-000774

Category Name: Casual Dresses

Price: $56.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Retro Crush Floral Chiffon Mini Dress
Serving vintage flirt energy in this floral mini dress. It brings the vibe with a breezy A-line fit, playful cutouts, and a tie-front bust made for sunny days.

Fit & Features
- Vintage-inspired floral print
- Chiffon fabric, smooth woven lining
- V-neckline, tie-front bust, adjustable spaghetti straps
- Stretchy smocked back panel
- Side cutouts along the bodice
- A-line fit, ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000775

Category Name: Casual Dresses

Price: $49.90

Availability: In Stock

Available Color: LAVENDER

Available Size: S, M, L
Polished But Fun Skater Mini Dress
Clean, classic… and cuing all the compliments. This striped skater mini dress brings that tailored, put-together vibe with a cinched bodice and flared skirt perfect for sunny days.

Fit & Features
- Striped pattern, linen-like woven fabric
- Square neckline, spaghetti straps
- Hidden side pockets
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000776

Category Name: Casual Dresses

Price: $56.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L
Flirty Confidence Lace One-Shoulder Mini Dress
A little bold, a little soft—exactly the balance you were going for. This lace one-shoulder A-line mini dress hugs up top and flares at the hem, giving you that confident, caught-in-the-moment kind of vibe.

Fit & Features
- Lace fabric with knit lining, high stretch
- Sleeveless one-shoulder neckline, tank straps
- Fitted bodice, ruched detailing
- Drop waist design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000778

Category Name: Casual Dresses

Price: $39.90

Availability: In Stock

Available Color: YELLOW

Available Size: S, M, L
Polka Dot Plans Ruffle Mini Tube Dress
The dress code? Looking effortlessly put together. This polka dot mini tube dress combines a curve-hugging fit with a playful, ruffled, A-line hem, making it an easy pick for brunch dates, party invites, and any excuse to wear something cute.

Fit & Features
- Mesh fabric with knit lining, high stretch
- Polka dot print
- Strapless straight-across neckline
- Drop waist
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000780

Category Name: Casual Dresses

Price: $34.90

Availability: In Stock

Available Color: BLUE

Available Size: XS, S, M, L
Pretty Little Tie-Back Skater Dress
The kind of dress that makes plans for you. This chiffon skater dress with a sweetheart neckline, lace trim, and tie-back detail feels light, flirty, and ready for any plans.

Fit & Features
- Swiss dot chiffon fabric, smooth woven lining
- Sweetheart lace trim neckline
- Adjustable spaghetti straps
- Open tie-back design, stretchy smocked panel
- Sheer lace trim waist insert
- Skater silhouette, lace trim ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000777

Category Name: Casual Dresses

Price: $59.90

Availability: In Stock

Available Color: WHITE, BLACK

Available Size: S, M, L
Romantic Eyelet Lace Skater Mini Dress
Romantic details make this dress feel polished. The lace bodice and embroidered eyelet skirt create rich texture, while the scalloped hem adds a delicate finish. It’s an easy pick for brunches, showers, and daytime celebrations.

Fit & Features
- Airy cotton-blend woven fabric with lining, no stretch
- V-neckline with ruffled trim, wide tank straps
- Sheer lace bodice with embroidered detailing, lined bust
- Front hook-eye closures
- Smocked back panel
- Eyelet skater mini-length skirt with scalloped hem
- Runs true to size
Style Number/Barcode: 05102-000783

Category Name: Casual Dresses

Price: $45.90

Availability: In Stock

Available Color: BLACK, WHITE

Available Size: S, M, L
Product Badge:
- New Arrival
Chic Agenda Plunge Maxi Dress
From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.

Fit & Features
- Smooth knit stretch fabric
- Cao sleeves with shoulder pads for structure
- Plunge V-neckline
- Center front drape and slit designs
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000784

Category Name: Casual Dresses

Price: $59.90

Availability: In Stock

Available Color: TAUPE

Available Size: S, M, L
Weekend Romance Floral Cotton Midi Dress
Feels like a soft yes to every plan on your calendar. This flowy ruffle midi dress brings an easy, romantic fit with a smocked waist and tie back, perfect for brunch, showers, or vacations.

Fit & Features
- Dainty floral pattern, cotton woven fabric and lining
- Sleeveless ruffle trim V-neckline
- Button front bust accents, stretchy smocked panel
- Tie-back design
- A-line silhouette, ruffled midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001392

Category Name: Casual Dresses

Price: $64.90

Availability: In Stock

Available Color: IVORY

Available Size: S, M, L
RSVP To Sunshine Striped Mini Dress
This striped halter mini dress hugs in all the right places with a flattering curve-hugging fit that’s made for brunch, beach city strolls, and vacations.

Fit & Features
- Striped pattern, ribbed knit fabric, knit lining, high stretch
- Halter V-neckline with tie straps
- Partially open back
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000785

Category Name: Casual Dresses

Price: $34.90

Availability: In Stock

Available Color: GREEN

Available Size: XS, S, M, L
Effortlessly Booked Midi Dress
The kind of dress that makes last-minute reservations feel completely intentional. This open back midi dress combines a sleek body-skimming fit with a draped sash detail for an elevated look that works everywhere from cocktail parties to weddings.

Fit & Features
- Slinky knit double-lined fabric
- Sleeveless boat neckline
- Open back, center back slit
- Form-hugging midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000816

Category Name: Casual Dresses

Price: $42.90

Availability: In Stock

Available Color: NAVY

Available Size: XS, S, M, L
Late Dinner Plans Tube Maxi Dress
This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.

Fit & Features
- Soft jersey knit fabric, stretchy lining
- Strapless tube neckline, non-slip grip lining
- Ruched fitted bodice
- Flowy curve-hugging silhouette
- Shark-cut maxi hem
- Runs true to size
Style Number/Barcode: 05102-000787

Category Name: Casual Dresses

Price: $52.90

Availability: In Stock

Available Color: BLACK

Available Size: M, L
In Your Good Graces Halter Mini Dress
Sweet, but make it a little unexpected. This halter mini skims your shape with a soft, textured feel and a lace trim hem that adds just enough detail for showers, graduations, or dressy brunch plans.

Fit & Features
- Textured chiffon fabric, sewn in knit stretchy lining
- High halter neckline with tie straps
- Open back
- Bodycon mini silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 05102-000794

Category Name: Casual Dresses

Price: $44.90

Availability: In Stock

Available Color: WHITE

Available Size: S, M, L
Striking Zebra Mesh Bodycon Mini Dress
Animal print is back in its boldest form. This mesh mini dress updates the trend with a curve-skimming fit, halter neckline, and ruffled hem for added movement. It’s made for nights when a minimal outfit is not the plan.

Fit & Features
- Zebra print, lined mesh fabric
- Halter V-neckline
- Curve-hugging fit
- Asymmetrical ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000795

Category Name: Casual Dresses

Price: $36.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Product Badge:
- New Arrival
Worth The Stare Striped Knit Midi Dress
This striped sweater dress does all the hard work the second it’s on. The body-hugging fit and trending striped pattern were made for dinners out, cocktail parties, and walking in fashionably late.

Fit & Features
- Ribbed knit fabric, high stretch
- Vertical striped pattern
- Strapless sweetheart neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000420

Category Name: Casual Dresses

Price: $44.90

Availability: In Stock

Available Color: BLACK

Available Size: L
Product Badge:
- Best Seller
Back For More Halter Mini Dress
All eyes on you always. This knit mini dress hugs your shape with side ruching and an open-back moment that keeps the focus on you.

Fit & Features
- Sweater knit fabric, moderate stretch
- High halter neckline with tie straps
- Open back, adjustable strap
- Side ruched seams
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000419

Category Name: Casual Dresses

Price: $17.97 $42.90

On Sale: Yes

Availability: In Stock

Available Color: LAVENDER

Available Size: L
Product Badge:
- Sale

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