Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Own The Moment Tube Floral Maxi Dress
Ready to shut down the vacation pics? This strapless floral maxi dress brings effortless chic with a curve-hugging fit and leg-baring side slit.
Fit & Features
- Floral print, mesh-lined fabric, moderate stretch
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000237
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Paradise Tropical Slit Maxi Dress
Make a statement in this tropical maxi dress on your next visit to paradise! This stunning strapless maxi dress features an alluring side cutout and flirty side slit that creates movement with every step.
Fit & Features
- Tropical print, smooth knit stretchy fabric
- Strapless neckline
- Side cutout with adjustable drawstring
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000138
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic On Vacay Geometric Print Maxi Tube Dress
You'll be chic on vacay in this trendy maxi tube dress designed with a lightweight woven fabric with a bold geometric print. The strapless bodice features a V-shaped front overlay with a fringe trim, leading to a long-length fitted silhouette with a thigh-high side slit to show off some leg.
Fit & Features
- Woven fabric with woven lining, no stretch
- Geometric print
- Strapless straight-across neckline, no-slip strip
- V-shaped front overlay, fringe trim
- Tie-back design, lower open back, hidden zipper with hook-eye closure
- High-cut side slit
- Maxi-length fitted silhouette
Style Number/Barcode: 05102-000142
Category Name: Casual Dresses
Price: $9.97 $46.90
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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Jungle Luxe Backless Maxi Dress
Unapologetically bold, this maxi dress is made for making an entrance. The plunging halter neckline and curve-hugging fit keep it sleek, while the strappy lace-up back and animal print bring all the wild energy.
Fit & Features
- Animal multi-print design, stretchy knit fabric
- Halter plunge neckline
- Strappy back with hard trim insets
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000473
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wildflower Hour Lace A-Line Mini Dress
Flirty meets sultry in one perfect dress. With a draped cowl neck and delicate floral lace, this A-line mini dress hugs every curve, serving up major after-dark romance.
Fit & Features
- Floral print, lace fabric lined with stretch knit
- Cowl neckline, padded bra cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000477
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Dream Strapless Belted Skater Dress
She’s giving flirty, fun, and just the right amount of edge. The strapless fit and belted waist make this denim skater dress the definition of standout style.
Fit & Features
- Denim fabric
- Strapless fold-over neckline
- Smocked back
- Belted drop waist
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000232
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Studded Rodeo Denim Mini Dress
Cowgirl meets cool-girl—this strapless denim mini dress unveils an edgy side with studded designs that bring just the right amount of cute to your Western vibe. Perfect for bachelorettes, concerts, or a night at the country bar.
Fit & Features
- Denim fabric
- Strapless neckline
- Back zipper closure
- Front studded trim design
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000231
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Saddle Up Cow Print Denim Mini Dress
Serving western attitude with a side of yeehaw chaos. This cow-print mini dress brings the edge with a snap-front design and pockets for full rodeo realness.
Fit & Features
- Cow print, cotton denim fabric, no stretch
- Sleeveless V-neckline
- Button front closures
- Two front pockets
- Curve-hugging fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000230
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Cutie Ribbed Knit Halter Midi Dress
Show up to happy hour looking like a chic cutie in this halter midi dress designed with hacci ribbed knit fabric for plenty of stretch. The tie-back halter straps lead to an alluring open back, while the curve-hugging fit flaunts your gorgeous figure.
Fit & Features
- Hacci ribbed knit fabric, high stretch, sewn-in knit lining
- Sleeveless V-neckline
- Tie-back halter straps
- Open back, lower ruched seam
- Midi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000149
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All In The Flirt Halter Mini Dress
Catch all the compliments. This mini halter dress features a fitted bodice and a flirty, layered skirt, perfect for your next sunny day brunch or a cute date night!
Fit & Features
- Smooth knit fabric
- Square neckline
- Wide shoulder straps
- Low-back cut design
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000228
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Flirt Striped Mini Dress
Cozy yet flirty—this striped sweater mini dress hugs your curves with a snug knit and a sultry off-shoulder neckline. Pair it with boots or heels for the perfect fall night-out look.
Fit & Features
- Striped pattern, stretch knit fabric
- Folded off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000119
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fireside Flirt Off-The-Shoulder Midi Dress
Minimal effort, maximum slay—this knit midi dress is the definition of chic. With its off-shoulder neckline, peekaboo cutout, and side slit, it’s your new go-to for dinner dates or rooftop wine bars.
Fit & Features
- Stretch rib knit fabric
- Off-the-shoulder neckline
- Fitted long sleeves
- Cutout bodice
- Front slit and button accents
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000118
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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It Girl High Neck Lace Up Maxi Dress
That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you.
Fit & Features
- Texture knit fabric, knit lining
- High neckline
- Spaghetti straps
- Lace-up back
- Bodycon fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000108
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Ruffles Mini Tube Dress
Serving ruffles and bold girl confidence—this tube mini dress does the most. With a curve-hugging fit and layers of mesh ruffles, it's your plus-one for rooftop parties, flirty photo ops, and every standout moment in between.
Fit & Features
- Knit fabric with knit lining, high stretch
- Mesh ruffled design
- Strapless tube neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000224
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes on You Lace Low Back Midi Dress
Soft girl era, but make it spicy. With a sheer midi hem, sultry low back, and flirty side slit, this is the “accidentally iconic” dress for nights out, beach dates, or brunches.
Fit & Features
- Stretch lace knit fabric, partially lined
- V-neckline, spaghetti straps
- Low back cut
- Curve-hugging silhouette
- Sheer midi hem, side slit
- Runs true to size
Style Number/Barcode: 05102-000222
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Body Language Tube Mini Dress
Warning: may cause jaw drops. With a sleek tube neckline and a sultry cutout, this bodycon mini dress is serving curvy drama all night long!
Fit & Features
- Soft knit stretchy fabric, smooth knit lining
- Strapless tube neckline
- Side cutout bodice, draped accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000226
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spice It Up Cutout Midi Dress
Serving sultry vibes with zero effort required. This knit midi hugs in all the right places with a bold cutout back and leg slit that was made for double takes.
Fit & Features
- Textured knit fabric with stretch
- V-neckline, tank shoulder straps
- Open back cutout with racer strap detail
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000109
Category Name: Casual Dresses
Price: $12.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Thing Mesh Belted Strap Mini Dress
Equal parts fierce and flirty, this mesh mini dress brings major attitude with western-inspired belted straps and a ruffled hem that keeps it playful. The mesh scoop neckline and ruched sides seal the deal.
Fit & Features
- Mesh fabric lined with stretch knit
- Scoop neckline
- Back zipper and hook-eye closure
- Faux leather Western-inspired belted shoulder straps
- Side ruched seams, form-hugging bodice
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000225
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Cute And Cool Denim Mini Dress
Weekend plans? Sorted. This zip-front denim mini dress keeps it casual but still put-together, with a belted waist that flatters every move. Pair with sleek boots for the perfect edgy fall vibe.
Fit & Features
- Denim fabric
- Sleeveless collared neckline
- Zip-up front closure
- Belted waist
- Front pockets
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000223
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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More To Come Tube Skater Dress
Perfect for day or night fun, this tube mini dress features playful ruffles that add a flirty touch while the skater silhouette flatters every figure with a fun, twirl-worthy flare.
Fit & Features
- Lined knit fabric, high stretch
- Strapless tube neckline
- Skater silhouette
- Ruffled mini-length hem, lace trimming
- Runs true to size
Style Number/Barcode: 05102-000766
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Breezy Summer Strapless Tiered Midi Dress
This flowy gauze midi dress is perfect for those breezy summer vibes, featuring a strapless smocked bodice and tiered A-line silhouette. Style with mules for sunset happy hour!
Fit & Features
- Gauze woven fabric
- Strapless straight-across neckline
- Smocked bodice
- Empire waist seam
- Midi-length hem, tiered design
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000144
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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No Rules Leopard Long Sleeve Mini Dress
A little wild, a lot confident. This mini dress brings fierce animal print, gold stud accents, and a body-hugging fit that’s made to turn heads—because blending in was never the plan.
Fit & Features
- Leopard print, mesh-lined stretchy fabric
- Crew neck
- Fitted long sleeves
- Studded embellishments
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000218
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Bloom Mesh Mini Dress
Soft meets fierce in this mesh dress—floral, animal print, and all eyes on you. The open back and flared sleeves bring that extra touch for plans that need a little drama.
Fit & Features
- Floral, leopard print, mesh fabric, stretchy knit lining
- Boat neckline
- Long flared sleeves
- Open back with adjustable tie closure
- Form-hugging silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000217
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free