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!
-
Sweet Escape Eyelet Mini Dress
This one belongs at sunset dinners, rooftop pics, and every RSVP you almost skipped. The eyelet mini dress hugs just right through the bodice with an easy flared fit that keeps it cute and comfortable all night.
Fit & Features
- Lightweight eyelet fabrication, knit lining
- Off-the-shoulder neckline
- Draped cold shoulder accents
- Ruched bodice
- A-line silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000691
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
-
Perfect Plans Ribbed Knit Halter Skater Dress
RSVP’d in five minutes because this dress already handled the outfit. This ribbed knit halter skater dress hugs through the waist, flares just right, and is basically made for parties, birthday dinners, and last-minute “be ready at 8” texts.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless V-neckline
- Halter strap, partially open back
- Pleated detailing
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000291
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: PINK, WHITE, YELLOW, MINT, LIGHT, BLUE
Available Size: XS, S, M, L
-
Flirty And Flowy Ribbed Knit Strapless Skater Dress
Ready before the group chat even replies. This ribbed knit strapless skater dress hugs through the bodice with a flirty drop waist and flowy skirt that moves with you from brunch plans to last-minute invites.
Fit & Features
- Ribbed knit fabric, high stretch
Strapless straight-across neckline - Drop waist design
- Godet detailing
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000008
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Ribbed knit fabric, high stretch
-
Bold Moves Fringe Bandage Maxi Dress
When the invite says dress to impress, this fringe bandage maxi dress understood the assignment. Designed in a sculpting bodycon fit with a strapless neckline and flowy maxi-length fringe, it hugs in all the right places and moves with you from dinner plans to the dance floor.
Fit & Features
- Structured bandage knit fabric, moderate stretch
- Strapless straight-across neckline
- Bodycon silhouette
- Mini-length hem
- Maxi-length fringe design
- Runs true to size
Style Number/Barcode: 05103-000865
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Brunch Flirt Polka Dot Ruffle Skater Dress
Sweet and flirty, this polka dot mesh babydoll dress brings the ruffle, the lace-up back, and that floaty skater shape that’s made for brunch plans and your fab weekend festivities.
Fit & Features
- Mesh fabric with lining
- Dainty polka dot print
- Sleeveless V-neckline, ruched bust and bodice
- Adjustable spaghetti straps
- Open cross-back lace-up design, tie closure
- Tiered ruffled short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001099
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Plans In Bloom Floral Chiffon Babydoll Dress
RSVP yes, figure out the details later. This floral chiffon babydoll dress is light, flirty, and effortless with its ruched sweetheart neckline and open tie-back—basically your go-to when the group chat says brunch, birthday, or both.
Fit & Features
- Chiffon fabric with lining
- Floral print
- Sleeveless sweetheart neckline, ruched bust
- Adjustable spaghetti straps
- Open back, tie-back design
- Mini-length babydoll silhouette
- Runs true to size
Style Number/Barcode: 05101-000878
Category Name: Casual Dresses
Price: $52.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Bare Shoulder Mood Bodycon Midi Dress
Shoulders out, confidence locked in. This ribbed bodycon midi dress contours your shape with a foldover neckline that flaunts some skin. Perfect for showers, graduations, or any dressed-up plans.
Fit & Features
- Soft rib knit fabric
- Foldover off-the-shoulder neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000695
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
-
Flirty Vibes Strapless A-Line Mini Dress
This is your flirty little upgrade when you want to feel instantly put-together. The strapless A-line mini dress hugs up top, skims the body, and finishes with a playful ruffle that moves with you.
Fit & Features
- Brushed knit fabric, high stretch
- Strapless sweetheart neckline
- Drop waist, ruched detailing
- Tiered ruffled design
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000697
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
-
Risk Taker Crew Neck Lace-Up Mini Dress
Not your average little black dress. This ribbed mini dress features a bold lace-up grommet front and high neckline that sculpt and define, giving you a sleek, body-hugging fit that’s ready for happy hour, concerts, and last-minute plans.
Fit & Features
- Rib knit stretchy fabric
- Crew neck
- Front lace-up grommet
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000282
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
-
Daydream Darling Babydoll Mini Dress
Your soft-girl moment just called. This puff sleeve mini dress features an open tie back and breezy cotton blend woven fabric that feels easy, romantic, and perfect for brunch, showers, and any weekend fun.
Fit & Features
- Cotton-blend woven fabric, woven lining
- Puff short sleeves
- Square neckline
- Open tie-back design
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000698
Category Name: Casual Dresses
Price: $45.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Heat Tube Maxi Dress
This strapless rib knit bodycon maxi dress hugs you just right and features a side floral crochet accent that feels equal parts flirty and elevated for dinners, birthdays, and any weekend plans.
Fit & Features
- Rib knit fabric with stretch
- Strapless neckline
- Side floral crochet accent
- Bdoycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000345
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: M, L, XL
-
Bold Bloom Floral Knit Midi Tube Dress
Big blooms, bold plans. This floral knit midi tube dress hugs in all the right places with a sleek bodycon fit and effortless strapless neckline—perfect for brunch dates, rooftop drinks, or any moment that deserves a standout look.
Fit & Features
- Ribbed knit fabric, moderate stretch
- Large floral print
- Strapless neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000344
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Sleek Aura Open Back Midi Dress
Sleek, sculpting, and ready for any occasion, this midi dress keeps all eyes on you.The high neckline keeps it polished, while the open back does all the talking when you walk away.
Fit & Features
- Stretch knit fabric
- Cowl high halter neckline
- Open back
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000699
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Going Somewhere Cute Mini Dress
The kind of dress you'll love this season. With a sculpting bodycon fit and all-over ruching, this mini dress keeps things sleek, flattering, and easy to dress up or down.
Fit & Features
- Stretchy knit fabric, double-lined
- Crew neck
- Short sleeves
- Ruched bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000703
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- New Arrival
-
Keep It Cute Bodycon Mini Dress
This one just feels like a good idea. A ruched tank mini dress that smooths and shapes with a barely-there feel, made for last-minute plans you’re definitely saying yes to.
Fit & Features
- Smooth knit-lined stretch fabrication
- V-neckline with tank straps
- All-over ruched detailing
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000704
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
-
Sweet Heat Floral Chiffon Mini Dress
This floral mini dress is flirty, a little bold, and made for vacations, weekend plans, and showers. The halter tie and front cutout bring the drama, while the soft ruffles and A-line fit keep it balanced and feminine.
Fit & Features
- Floral print, chiffon-lined fabric
- Halter sweetheart neckline, tie straps
- Cutout side and back
- Ruffled detailing
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000705
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: YELLOW, RED
Available Size: M, L
-
Sweet On Plans Polka Dot Mini Dress
Caught mid-stroll and looking sweet in this polka dot dress. This dress hugs just right with a form-hugging fit and a flirty ruffle hem made for daytime plans.
Fit & Features
- Polka dot print, knit, stretchy fabric
- One-shoulder neckline
- Form-hugging ruched fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000710
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
-
Darling Off-Shoulder Skater Dress
This chiffon mini dress features an off-the-shoulder ruffle neckline with delicate lace trim and a flirty skater skirt, creating a dreamy silhouette perfect for family brunches, bridal events, and dressy occasions.
Fit & Features
- Chiffon-lined fabric
- Ruffle trim off-the-shoulder neckline, tie-front
- Corset-seamed bodice
- Skater silhouette, drop waist seam
- Lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000684
Category Name: Casual Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Sunkissed Curve Knit Midi Dress
This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.
Fit & Features
- Striped print, rib knit fabric
- Sweetheart neckline, cutout bust accent
- Adjustable spaghetti straps
- Bodycon fit
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000084
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Best Seller
-
Caught Daydreaming Polka Dot Mini Dress
Serving flirty little getaway vibes in this polka dot dress! It features a breezy blouson fit and a tiered ruffle skirt that moves perfectly from brunch to spontaneous plans.
Fit & Features
- Polka dot print, mesh fabric, smooth lining
- Strapless tube neckline
- Blouson relaxed bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000716
Category Name: Casual Dresses
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Make Plans Eyelet Ruffle Mini Dress
Last-minute plans just got a major upgrade. This eyelet ruffle mini dress hugs through the bodice with a flirty drop waist and tiered skirt that’s made for showing up and standing out.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Fitted bodice, ruched detailing
- Drop waist seam
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000715
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
-
Brunch Plans Floral Chiffon Skater Dress
Brunch turned into all-day plans? You’re covered. This floral chiffon skater dress keeps it light and flirty with a tie-back detail and a layered ruffle skirt that moves with you.
Fit & Features
- Sheer chiffon fabric with lining, floral print
- Sleeveless square neckline
- Adjustable spaghetti straps
- Open back, tie-back design, hidden zipper and hook-eye closure
- Tiered ruffled design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000719
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLUE
Available Size: L
-
Minimal Muse Bodycon Midi Dress
Your new go-to dress when the vibe is effortlessly polished. This bodycon midi dress hugs in all the right places while the side slit offers effortless allure for brunch plans, vacations, or sunset cocktails.
Fit & Features
- Sweater knit fabric
- Scoop neckline
- Adjustable spaghetti straps
- Side slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000349
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: TAUPE, ORANGE, MAGENTA
Available Size: S, M, L
-
Boldly Sweet Lace Ruffle Mini Dress
This one does all the talking. The lace texture, flirty cutout, and tiered ruffle skirt bring just the right mix of soft and statement. It’s made for date nights, parties, or anytime you want to feel a little extra.
Fit & Features
- Lace-lined fabric
- Sweetheart neckline, keyhole cutout
- Adjustable spaghetti straps
- Skater ruffle silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001057
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XXS, XS, S, M, L