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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Sunset Plans Chevron Crochet Maxi Dress
This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.
Fit & Features
- Chevron striped pattern
- Crochet knit lined fabric
- V-neck, spaghetti straps
- Lace-up back
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000418
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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Island After Hours One Shoulder Maxi Dress
This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.
Fit & Features
- Tropical floral print knit fabric
- One-shoulder neckline
- Statement hardware strap detail
- Front slit with ruffle accent
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-000419
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, XL
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Cozy Allure Cable Knit Mini Dress
Chic meets snuggly. This off-the-shoulder sweater dress hugs your curves with cable-knit texture while keeping things flirty and polished—perfect for autumn plans, latte runs, or cozy dinners out.
Fit & Features
- Cable knit fabric, moderate stretch
- Folded off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000157
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Plans Ruffle A-Line Romper
Your plans just found their outfit—this romper is all about fun with a flirty edge. The tie-back halter straps, ruffle overlay, and A-line fit make it a go-to for nights out or weekend parties.
Fit & Features
- Smooth knit fabric, high stretch
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Ruching, drop waist
- Mini-length tiered ruffle overlay, hidden fitted shorts
- Romper in size small is 29" shoulder to hem with a 9" front rise and a 1" inseam
- Runs true to size
Style Number/Barcode: 06503-000155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace-Up Moment Sheer Long Sleeve Mini Dress
Bring the drama without even trying—this long sleeve mini dress is sheer perfection. With a lace-up front and ruffle trim, it’s the flirty and fab style your night-out look needs.
Fit & Features
- Sheer mesh fabric with partial knit lining, high stretch
- Plunging V-neckline, lace-up front with tie closure, ruffle trim
- Sheer long fitted sleeves
- Hidden back zipper with hook-eye closure
- Drop waist seam
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000401
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer mesh fabric with partial knit lining, high stretch
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Invite Only Rhinestone Floral Dress
You weren’t planning on being the best dressed—but here we are. This strapless mini dress with a rhinestone floral detail brings just enough shine for every invite on your calendar.
Fit & Features
- Mesh-lined fabric
- Strapless tube neckline
- Side rhinestone floral embellishment
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000423
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Majorly Chic Ribbed Knit Mock Neck Midi Dress
Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates.
Fit & Features
- Ribbed hacci knit fabric with knit lining, high stretch
- Sleeveless mock neckline
- Keyhole cutout at the bust
- Angled seams under the bust
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000422
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Wild Intentions Zebra Velvet Maxi Dress
A little wild, a lot unforgettable. This burnout zebra velvet mesh maxi brings high-drama energy with its one-shoulder neckline, side cutout, and ruched bungee drawstring that lets you play with the slit height. Equal parts sleek and scandalous—just how we like it.
Fit & Features
- Zebra burnout velvet pattern, mesh fabric, sewn-in mesh lining
- One-shoulder neckline, bungee spaghetti strap
- Strappy back, bodice side cutout
- High front slit and ruched drawstring bungee cord
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000757
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Trouble Halter Romper
Playful yet bold. This halter plunge romper stuns with cascading ruffles and a flirty fit that’s ready for parties or date nights.
Fit & Features
- Smooth knit-lined stretchy fabric
- Plunge halter neckline, tie closure
- Side ruched seams
- Ruffled layer mini-length hem, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000192
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Buttoned Up Charm Off-The-Shoulder Mini Dress
Sophisticated with a sultry twist, this rib knit mini serves clean lines and gold button details that pop. Perfect for lunch dates, weekend looks, or when you want polished but playful.
Fit & Features
- Rib knit fabric, moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Button front accents
- Faux front pockets
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000155
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Petal Noir Floral Chiffon Maxi Dress
This halter maxi dress stuns with a draped cowl neckline, bold floral print, and a daring open back that leaves a lasting impression. Flowing and form-flattering, it’s your go-to for romantic date nights and elevated occasions.
Fit & Features
- Floral print, chiffon-lined fabric
- Halter cowl neckline
- Open back design, zipper and hook-eye closure
- Curve-hugging silhouette
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000577
Category Name: Casual Dresses
Price: $56.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Golden Hour Energy Tube Mini Dress
This dress feels like golden hour bottled up. The abstract mesh, bold cutouts, and flowing sash bring a confident, getaway-ready vibe made for warm nights!
Fit & Features
- Stretch mesh-lined fabric with an abstract printed design
- Strapless tube neckline
- Front cutout detail for a bold silhouette
- Attached sash detail
- Mini length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-000421
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Glow Strapless Maxi Dress
Serving sunkissed confidence with every step. The strapless lace maxi dress contours through the bodice, highlights the neckline with hardware detail, and falls into a sleek, elongating shape that feels equal parts elevated and effortless.
Fit & Features
- Striped design, lace-lined fabric
- Strapless sweetheart neckline, hardware insert, non-slip grip lining
- Form-hugging
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000425
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Sunset Swirl Lace-Up Maxi Dress
Serve vacation glow from every angle in this striped maxi dress. This dress hugs your curves while the crisscross lace-up back and flared mermaid hem bring the drama for cocktails and dinners with a view.
Fit & Features
- Striped pattern, crochet knit lined fabric
- V-neckline with tie front detail
- Spaghetti straps shape the strappy lace-up back
- Mermaid flared maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000426
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
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Vacay Sparkle Tropical Sequin Mini Dress
Booked the trip and packed the drama. This tropical floral sequin tube bodycon mini dress hugs close with a glossy, light-catching finish that was made for sunset cocktails and flash photography.
Fit & Features
- Tropical floral, sequin mesh fabric, sewn-in lining
- Tube strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- Bodycon mini fit
- Runs true to size
Style Number/Barcode: 05102-000427
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Back It Up Denim Halter Mini Dress
Classic denim, unexpected angles. This halter mini dress brings a sleek, body-con fit with an open back moment that feels equal parts polished and playful—perfect for day plans, concerts, or festivals.
Fit & Features
- Light wash denim fabric
- Halter collar neckline
- Button front
- Open back with 8 patchwork detail
- Bodycon silhouette
- Classic jean styling, mini-length micro hem
- Runs true to size
Style Number/Barcode: 05102-000429
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: LIGHT, DENIM
Available Size: XS, S, M, L
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Seaside Glamour Crochet Strapless Mini Dress
Serving seaside glamour. This seashell crochet mini dress hugs in all the right places, with a strapless sweetheart neckline and textured crochet knit, ready for beach clubs, sunset dinners, and every vacation photo moment.
Fit & Features
- Sheer crochet knit fabric with lining
- Seashell embellishments
- Strapless sweetheart neckline, padded bust
- Back zipper closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000430
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Sweet Plans Ahead Ditsy Floral Print Skater Dress
This dress gets compliments before you even say hi. The ditsy floral print, smocked bodice, and tiered ruffle skater silhouette make it the easiest pick for brunch dates, garden parties, and every cute plan on your calendar.
Fit & Features
- Woven gauze fabric with ditsy floral print
- Sleeveless V-neckline
- Halter tie-back straps, partially open back
- Stretchy smocked bodice
- Lace inserts, tiered ruffled design
- Mini-length hem with lace trim, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000432
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L, XL
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City Girl Denim Halter Mini Dress
Denim, but make it the main character. This halter mini dress features a sharp collar, flattering V-neckline, and curve-hugging seams that flatter your figure, giving you an effortless look this season.
Fit & Features
- Denim fabric with stretch
- Collared V-neckline, sleeveless design
- Open back, zipper and hook-eye closure
- Curve-contouring seams, front pockets
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000431
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Written In Roses Strapless Midi Dress
This one doesn’t rush—it lingers. A strapless silhouette with a fluid floral print and front slit that moves easily, feels confident, and looks unforgettable from every angle.
Fit & Features
- Floral print, mesh-lined stretchy fabric
- Strapless neckline
- Front slit for movement
- Curve-hugging midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000433
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: RED
Available Size: XS, S
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Café Plans Polka Dot Halter Mini Dress
Easy, breezy, and perfectly on schedule for an afternoon out. This polka dot halter mini feels light, moves with you, and looks chic for brunches, iced coffees, and spontaneous photo ops.
Fit & Features
- Polka dot print chiffon fabric with woven lining
- Halter neckline with open back detail
- Back zipper and hook-eye closure
- Fitted bodice with subtle shaping seams
- A-line mini skirt with godet flare panels
- Runs true to size
Style Number/Barcode: 05102-000435
Category Name: Casual Dresses
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Drama Off Shoulder Side Tie Mini Dress
This mini dress mixes soft draping with curve-hugging ruching for a look that reads chic without trying too hard. The off-the-shoulder neckline and dramatic side tie keep things flirty, polished, and ready for whatever the night turns into.
Fit & Features
- Smooth knit stretch fabric
- Off-the-shoulder foldover neckline
- Long fitted sleeves with slight flare at the wrists
- Ruched bodice and sides for a contoured silhouette
- Side tie accent with extended drape detail
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000434
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bloom Mood Floral Midi Dress
Soft, romantic, and ready for compliments. This floral midi dress features a strapless neckline and textured knit eyelet fabric that hugs your shape while keeping the vibe perfect for brunch dates, showers, or sunny day plans.
Fit & Features
- Ditsy floral print, eyelet mesh-lined fabric
- Strapless neckline
- Bodycon fit
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000436
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Amalfi Mood Halter Skater Dress
Serving sunshine in dress form. This citrus print halter mini dress features a sweetheart neckline and breezy A-line skirt, making it the perfect pick for vacations, brunch, and sunny day plans.
Fit & Features
- Citrus multi-print, woven fabric with woven lining
- Sweetheart halter neckline
- Padded bra cups, non-slip grip lining
- Back zipper and hook-eye closure
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000438
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L