Casual Dresses

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.

  • 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:
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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:
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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

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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

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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
  • 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:
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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

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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
  • 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

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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:
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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
  • 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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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

  • 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:
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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
  • 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:
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