Casual Dresses
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.
Now Trending
STYLE SPOTLIGHT
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!
-
Hot Weather Plans Strapless Maxi Dress
Serving sunshine with zero effort. This strapless bodycon dress hugs in all the right places with a bold floral moment that makes getting dressed for vacations or weekend plans easy.
Fit & Features
- Tropical floral print, stretchy knit-lined fabric
- Strapless tube neckline
- Bodycon maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000721
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
-
Effortlessly Sculpted Bodycon Midi Dress
Serving sculpted silhouettes with effortless vibes. This bodycon midi dress hugs your curves with a ruched waist, V-neckline, and leg slit that knows how to make an entrance without doing too much.
Fit & Features
- Smooth nylon-lined fabric, high stretch
- Sleeveless V-neck and back design
- Tank straps
- Ruched waist
- High-cut side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000728
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
-
Weekend Glow A-Line Midi Tube Dress
Sunshine, but make it wearable. This A-Line midi tube dress hugs through the ruched bodice, then flows into an effortless, breezy silhouette that’s made for everything from brunch plans to last-minute invites.
Fit & Features
- Sleek knit fabric, high stretch
- Strapless straight-across neckline
- Fitted ruched bodice
- Maxi-length flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000722
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
-
Effortlessly Done One Shoulder Dress
Easy and elevated, this one-shoulder dress is the perfect plus-one for everything on your calendar. The one-shoulder moment and cinched waist keep it flattering, while the flowy skirt gives a trendy flare.
Fit & Features
- Woven fabric
- One-shoulder neckline with ruched tails
- Stretchy smocked fitted waist
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000730
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
-
Spotted And Booked Polka Dot A-Line Mini Dress
Already RSVP’d and now you have the dress. This polka dot A-line mini dress hugs just right up top, then flares for that easy, flirty fit you’ll wear from dinner plans to after.
Fit & Features
- Ribbed knit fabric, high stretch
- Polka dot print
- Sleeveless V-neckline, eyelet trim, bow detail
- Adjustable thin eyelet shoulder straps
- Mini-length hem, ruffled trim
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000729
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
-
No Questions Asked Mini Dress
This one doesn’t wait around. Command the room in this bodycon mini dress, offering a show of skin and a trendy hardware detail that pulls the look together. Pair with heels for a night out.
Fit & Features
- Texture knit fabric
- Plunge cutout neckline, hardware insert
- Adjustable spaghetti straps
- Cutout back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000309
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
-
Love This For Me Halter Mini Dress
Soft, flirty, and already on your weekend lineup. This chiffon mini dress hugs your shape with a bodycon fit while the open back and ruffled trim keep things playful.
Fit & Features
- Chiffon fabric, smooth woven lining
- Sweetheart halter neckline, padded bra cups, tie straps
- Open back, stretchy smocked band
- Ruffled trim
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000732
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: YELLOW, PINK
Available Size: M, L, S
-
Vacation Flirt Striped Mini Dress
A little flirty on vacay without even trying. This striped bodycon dress hugs close with a strapless tube fit, front cutout neckline, and beaded strap accents that give you a stylish look.
Fit & Features
- Striped pattern, crinkle cotton-blend knit fabric
- Strapless tube neckline
- Front cutout with beaded strap accents
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000740
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Weekend Wandering Embroidered A-Line Midi Dress
Just add plans and let this do the rest. This embroidered A-line midi dress brings that easy, put-together feel with a breezy fit that works from brunch to wherever the day drifts next.
Fit & Features
- Woven fabric with lining, no stretch
- Embroidered pattern
- Sleeveless V-neckline
- Adjustable spaghetti straps, partially stretchy smocked back, zipper closure
- V-shaped waist seam, dual side pockets
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000749
Category Name: Casual Dresses
Price: $56.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
-
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
-
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
Product Badge:- New Arrival
-
Sweet Breeze Eyelet Mini Dress
This one feels like sunshine in dress form. The smocked bodice keeps it easy and flattering, while the tiered eyelet skirt adds flirty movement, perfect for showers, graduations, brunches, and any dressy plans.
Fit & Features
- Eyelet embroidered woven fabric, stretchy knit lining
- Strapless neckline
- Stretchy smocked bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001115
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Best Seller
-
Just Add Sunshine Floral Romper
This skater romper brings that effortless flirty vibe with a flowy fit and delicate floral feel that moves with you, perfect for brunch, showers, and any cute plans.
Fit & Features
- Floral print, woven fabric
- V-neckline with adjustable straps
- Skater romper silhouette with flowy skirt overlay
- Waist tie detail with tiered ruffle hem
- Runs true to size
Style Number/Barcode: 06403-000128
Category Name: Casual Dresses
Price: $49.90
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: $59.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Sunlit RSVP Lace Ruffle Romper
Soft lace, flirty ruffles, and that open-back tie moment make this halter romper perfect for showers, brunch, and vacations. Light, pretty, and impossible to ignore—in the best way.
Fit & Features
- Lace-lined fabric
- Plunge halter neckline, tie straps
- Strappy open back with tie
- Form-hugging fit
- Ruffled tiered mini-length hem
- Stretchy knit shorts lining
- Runs true to size
Style Number/Barcode: 06503-000263
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
-
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: $46.90
Availability: In Stock
Available Color: YELLOW
Available Size: 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
-
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
-
Cool Confidence Animal Print A-Line Mini Dress
A little wild, a lot unforgettable. This strappy abstract animal print A-line mini dress skims and sways with every step, giving you that effortless, throw-it-on-and-own-the-night kind of confidence.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract animal print
- Sleeveless sweetheart neckline, no-slip strip
- Cross-front spaghetti strap design leading to a tie-back halter design
- Open back design
- Mini-length asymmetric hem, flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000823
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Flirty Fit Lace Ruffle Romper
The one that instantly upgrades whatever’s on your calendar. A lace cutout ruffle romper with a flirty fit that’s made for parties, birthdays, and last-minute invites you’re definitely saying yes to.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Sleeveless plunging V-neckline, bar strap accent
- Halter tie-back spaghetti straps
- Open back, lower tie-back spaghetti straps
- Drop waist
- Tiered ruffled mini-length overlay, skater silhouette, hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000252
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: OFF, WHITE
Available Size: XS, S, M, L
-
A Bit Flirty Lace Halter Dress
This lace mini dress gives you that effortless twirl moment with a light, easy fit that feels made for bridal celebrations, birthdays, graduations, and every dressed-up moment.
Fit & Features
- Lace-lined fabric
- Halter neckline with tie straps
- A-line silhouette
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000950
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XXS, XS, S, M, L
-
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