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.
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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!
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Ultra Game NBA NY Knicks Mini Dress
Serving courtside energy even when you’re not at the game. This NBA Knicks halter mini dress hugs in all the right places with a sporty lace-up detail that keeps it playful and bold.
Fit & Features
- Jersey knit fabric, smooth knit lining
- Halter contrast trim neckline with tie straps
- Lace-up neckline with front and back Knicks graphic team logo
- Corset bodice, flexible boning
- Side zipper and hook-eye closure
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000548
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Ultra Game NBA LA Lakers Mini Dress
Game night, but make it stylish. This Los Angeles Lakers tube mini dress snatches with a structured bodice while the embroidered team logo and stud accents keep it bold from every angle.
Fit & Features
- Sleek knit-lined stretchy fabric
- Strapless tube neckline, padded bra cups
- Los Angeles Lakers embroidered team logo, mini stud accents
- Lace-up back design, side zipper and hook-eye closure
- High waist seam
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000549
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Stylish Plans Ribbed Knit Bodycon Midi Dress
One of those dresses that somehow does all the styling for you. This ribbed knit bodycon midi dress hugs just right with a notched V-neckline and sleek silhouette that works from casual plans to dressed-up moments.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless scoop neckline, notched V-neckline
- Thin tank shoulder straps
- Back slit accent
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000552
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLUE
Available Size: L
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Favorite Thing Sleeveless Midi Dress
The kind of dress that somehow works for every plan on your calendar. This rib knit bodycon midi dress keeps it chic and simple, perfect for dressing up or down.
Fit & Features
- Rib knit fabric, double-lined, stretchy
- Sleeveless scoop neckline
- Tank shoulder straps
- Bodycon silhouette
- Side slit, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000550
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Barely Trying Open Back Midi Dress
This is that effortless dress you reach for when you want to feel cute and put together. The open back adds a soft, unexpected moment, while the ribbed fit keeps everything sleek and flattering.
Fit & Features
- Rib knit stretchy fabric
- Scoop neckline
- Spaghetti straps
- Open back
- Side slit
- Form-hugging, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000553
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Desert Heat Faux Suede Strapless Mini Dress
This mini dress is doing the most in the best way. The faux suede strapless dress hugs in all the right places while the curved fringe detail brings the drama for nights out or festival plans.
Fit & Features
- Faux suede fabric, smooth knit lining
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Bodycon fit
- Curved seam detailing, curved front fringe trim
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000555
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS
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Flirt First Strapless Lace Tiered Mini Dress
Sweet at first glance, bold once you turn around. This strapless lace mini dress hugs through the bodice and finishes with playful tiered ruffles—made for nights that start casual and end unforgettable.
Fit & Features
- Stretch lace-lined fabric with a soft, floral texture
- Strapless neckline
- Drop waist silhouette
- Tiered ruffle skirt
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000557
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Plans Ahead Long Sleeve Skater Dress
Soft, cute, and already booked. This ribbed skater dress hugs up top and floats just right at the hem, making it an easy yes for brunches, daytime plans, and V-day dates!
Fit & Features
- Pointelle knit soft stretch fabric
- Crew neckline
- Fitted long sleeves
- Fitted bodice with a defining drop waist seam
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000556
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Vibe Ribbed Knit Mini Tube Dress
Simple, chic, and such a vibe. This ribbed knit mini tube dress hugs your curves with a comfy stretch fit—made for plans that come together at the last minute, but you still look fab.
Fit & Features
- Hacci ribbed knit fabric, high stretch, knit lining
- Strapless fold-over neckline
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000562
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Flirty Chic Cutout Maxi Dress
The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.
Fit & Features
- Gauze cotton woven fabric, woven lining
- Sweetheart neckline, spaghetti straps
- Open tie-back design
- Cutout bodice
- Hidden side pockets
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000559
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Wine Night Pinstripe Mini Dress
Clock out, but keep the attitude. This pinstripe mini dress brings tailored energy up top and flirty drama at the hem, hugging you in all the right places for wine bar nights and dinner.
Fit & Features
- Pinstriped pattern, woven fabric, sewn-in knit lining
- Strapless lace trim sweetheart neckline
- Padded bra cups
- Back zipper and hook-eye closure
- Ruched side lace panels
- Form-hugging fit, ruffled mini hem
- Runs true to size
Style Number/Barcode: 05102-000558
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
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Soft Glow Bodycon Mini Dress
Cute, simple, and effortlessly flattering. This ribbed knit bodycon mini dress hugs in all the right places with a clean square neckline and delicate straps, making it the perfect dress for day dates, brunch, or a casual night out.
Fit & Features
- Rib knit fabric, sewn-in lining
- Square neckline
- Spaghetti straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000560
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Styled Up Off-Shoulder Mini Dress
Easy, confident, and styled without overthinking. This off-the-shoulder blouson mini dress drapes up top with a fitted bottom that keeps the silhouette clean and pulled together for any plans that pop up.
Fit & Features
- Soft knit fabric with comfortable stretch
- Relaxed blouson top with a fitted mini skirt
- Off shoulder neckline
- Relaxed short sleeves
- Runs true to size
Style Number/Barcode: 05102-000563
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Polished Curves Off-Shoulder Knit Midi Dress
This midi dress keeps it classy with a side of allure—the foldover neckline, sleek rib knit, and gold hardware detail turn a timeless silhouette into a subtle showstopper. It’s the kind of dress that makes minimal feel magnetic.
Fit & Features
- Rib knit fabric
- Foldover off-shoulder neckline with hardware accent
- Long fitted sleeves
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000232
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Muse Floral Midi Dress
Soft florals and a sleek silhouette make this one an instant favorite. This strapless floral eyelet bodycon midi dress hugs your curves and adds a polished look for brunch, garden parties, and getaways.
Fit & Features
- Ditsy floral print, eyelet knit fabric, soft lining
- Strapless tube neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000570
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, L
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Sweet Talker Floral Eyelet Midi Tube Dress
Soft, fitted, and low-key stealing attention. This floral print eyelet midi tube dress hugs in all the right places with a stretchy feel that’s made for brunch plans, day dates, and everything after.
Fit & Features
- Eyelet knit fabric with sewn-in knit lining, high stretch
- Floral print
- Strapless elasticized straight-across neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000569
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Island Plans Tropical Tube Mini Dress
Booked, busy, and already packing this. This floral print mini dress hugs you in all the right places and was made for beach stays, resort destinations, and tropical escapes!
Fit & Features
- Slinky knit-lined stretchy fabric
- Tube strapless neckline
- Statement floral print
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000571
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Postcard From Paradise Maxi Dress
Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.
Fit & Features
- Multi-printed design, woven fabric
- V-neckline with trim and tie bust
- Spaghetti straps
- Lace-up tassel back
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000572
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Getaway Ready Floral Print Maxi Dress
Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!
Fit & Features
- Smooth knit stretchy fabric, knit lining
- Halter plunge neckline, hardware insert, adjustable cross back straps
- Open back design
- Cutout bosdice
- Flowy maxi-length silhouette with floral hem print
- Runs true to size
Style Number/Barcode: 05102-000576
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Darling Detail Strapless Midi Dress
Clean lines, zero effort, maximum compliments. This strapless midi dress hugs in all the right places with a textured knit feel that makes dinner plans, celebrations, and last-minute invites look very handled.
Fit & Features
- Textured knit-lined fabric
- Strapless neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000578
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Back To Bold Mock Neck Mini Dress
Minimal from the front, major from the back. This mini dress offers a bold cutout back with hoop accents and a bodycon fit that turns heads and gives your rotation a trendy upgrade.
Fit & Features
- Ribbed knit fabric with stretch
- Mock neckline with fitted long sleeves
- Sleek bodycon silhouette through the bodice
- Open-back cutout detail with a detachable hoop chain accent
- Mini-length skirt with a front side slit
- Runs true to size
Style Number/Barcode: 06005-000261
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Quietly Bold Lattice Side Midi Dress
This is the kind of dress that holds eye contact a second longer. Clean lines up front with a subtle lattice moment down the side make it feel polished, confident, and a little unexpected.
Fit & Features
- Ribbed knit fabric with stretch
- Square neckline
- Fitted long sleeves
- Side lattice cutout detailing
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000233
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS
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One More Pic Button Denim Dress
Serving attitude with every button. This denim mini dress hugs in all the right places with a lace-up back that makes the exit just as good as the entrance.
Fit & Features
- Denim fabric, vintage-inspired wash, high stretch
- Sleeveless baot neckline
- Front button-up closures
- Tailored seams
- Cutout lace-up strappy back
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000586
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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She's Bold Abstract Floral Midi Tube Dress
Fit & Features
- Sleek knit fabric, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Ruched detailing
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000585
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL