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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Mesmerizing Beauty Lace-Up Wrap Dress
Mesmerize with a wrap dress that showcases your best angles! The dress features a sleeveless scoop neckline, spaghetti straps, a lace-up back, a high slit, and a wrap silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit, Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back
- High slit
- Wrap silhouette
- Knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-0586
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Down Knit Midi Dress
For the modest yet trendy babe! This midi is a closet staple, whether it's work wear or a casual date night, just throw on some heels and you are lookin' gooood bb!
Fit & Features
- V- neckline | Long sleeves
- Oil slick buttons down the center
- Mid-length hemline
- Ribbed knit material
- Moderate stretch
- Form fitting silhouette
Style Number/Barcode: 06005-0516
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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New Love Ditsy Smocked Mini Dress
Something sweet, something new. Charm them all by slipping into the New Love mini dress! Pair with some sneakers for a girls' day and switch to some heels for date night with the boo!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline
- Mini Length Silhouette
- Woven Fabric I All Over Smocking
- Ditsy Floral Print I Tiered Ruffle Design
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0522
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Get Groovin' Tie Dye Scoop Neck Mini Dress
Get to movin' bb girl! This fab and fun mini dress features a splash of tie-dye print and goes perfect with white booties or sneakers!
Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Mini Length Hemline
- Smooth Brush Knit Fabric | Tie Dye Print
- Form Hugging Fit | Plenty Of Stretch
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0523
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunning Beauty Tropical Maxi Dress
Showcase your stunning beauty in this tropical maxi dress on your next weekend getaway! It features a sleeveless V neckline, spaghetti straps that lead to an open back with a strappy design, a high waist, and a floor-length hem with a relaxed fit. The knit fabric has an all-over palm leaf print to bring the vacay vibes. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V neckline
- Spaghetti straps
- Open back, strappy design
- High waist
- Floor-length hem, relaxed fit
- Knit fabric, palm leaf print
- Runs true to size
Style Number/Barcode: 05102-0525
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Me Back Tropical Maxi Dress
Get taken back to that dream vacay with a fab maxi dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a tropical print, an open back, a smocked waist, and a flowy maxi length silhouette. Complete with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Tropical print
- Open back
- Smocked waist
- Maxi length silhouette
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-0572
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleeveless V Neck Ruffled Floral Mini Dress
Get frilly in a ruffled floral dress. Celebrate with your squad in a floral mini dress that features a sleeveless bodice, a plunging V neckline, and spaghetti straps. The relaxed fit waist leads to a mini-length silhouette with a frilly ruffled hem. The all-over floral print features bright hues that contrast with the dark background. Complete your look with wedges and sunglasses.
Fit & Features
- Sleeveless V neckline
- Spaghetti straps
- Floral print
- Mini-length silhouette
- Ruffled hem
- Lightweight knit fabric with a moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0517
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty In Florals Midi Dress
Get a little flirty in pretty florals with this gorg printed midi dress!
Fit & Features
- Adjustable spaghetti straps | Cross back
- V neckline
- Ruched side detailing
- Asymmetric hem
- Mid-length, curve hugging fit
- All over floral print
- Knit fabric | Plenty of stretch
Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0516
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Falling For It Ruffled Chiffon Leopard Print Dress
Have them all falling for you when you step out in this flirty chiffon ruffled mini dress! Easily style with a pair of black mules and sweet pearl hoops!
Fit & Features
- Ruffle trim mock neckline
- Long sleeves with a ruffled wrist
- Relaxed bodice
- Stretchy smocked waist line
- Tired ruffled skirt
- Mini hemline | Lined at the skirt
- Slip on fit | No closures
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0513
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff Sleeve Leopard Print Mini Dress
Puff sleeves and leopard print - this mini dress couldn't get any trendier!
Fit & Features
- Off the shoulder neckline
- Short puff sleeves
- High waist seam
- Short, form hugging fit
- Leopard print
- Knit fabric | Plenty of stretch
- Form hugging fit
Style Number/Barcode: 05102-0521
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go Get 'Em Tiger Print Cowl Neck Mini Dress
Girl, go get em' in tiger print! We will always love our classic leopard print but have been gradually leaning into tiger to change it up and stand out a lil'! Pair with a leather jacket and boots, or black heels!
Fit & Features
- Cowl neckline
- Spaghetti straps that cross in the back
- Mini hemline
- Form fitting silhouette
- Side slit detail
- Lined at the bust | Lots of stretch
- Tiger print pattern
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0518
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Can't Forget Me Floral Side Ruched Mini Dress
Honey, they can't even take their eyes off of you! Walk around like the goddess you are in this figure-hugging mini dress! Don't forget to add some heels to really pull th look together for that brunch you got planned

Fits & Features
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Adjustable Spaghetti Straps
- V Neckline I Square Back
- Mini Length Silhouette
- Ruching Along Side Seam
- Stretchy Woven Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0520
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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Flowy In Floral Tie Waist Mini Dress
Charm them all with this pretty mini dress! It's perf for those upcoming warm and sunny days.
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Smocked Back
- Waist Tie Design
- Mini Length Silhouette I Wrap Skirt Design
- Crinkle, Gauze Lined Fabric I Floral Prints
- Moderate Stretch
Style Number/Barcode: 05102-0514
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Adjustable Spaghetti Straps
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Angora Knit Leopard Print Sweater Dress
Cozy and chic, this leopard print sweater dress is purrfect for the season.
Fit & Features
- Turtleneck
- Long sleeves
- Ribbed hems
- Leopard print
- Angora fuzzy knit fabric | Moderate stretch
- Relaxed, comfortable fit
Style Number/Barcode: 06005-0507
Category Name: Casual Dresses
Price: $4.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Bliss Smocked Mini Dress
Bring out the floral prints and wave those gloomy winter-blues goodbye! Radiate that early springtime energy in this cute mini dress!
Fits & Features
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Adjustable Spaghetti Straps
- Lettuce Edge Trim At Square Neckline & Hem
- Smocking Throughout
- Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05102-0519
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adjustable Spaghetti Straps
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Love For Leopard Mesh Mini Dress
Let your wild side come through in this killer mini dress!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline & Back
- Mini Length Silhouette I Ruching Along Sides & Center Back
- Leopard Print Throughout With Mesh Overlay I Smooth Knit Lining
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0512
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Fever Midi Dress
Get into that floral fever with this adorable ditsy floral printed midi dress, perf for spring!
Fit & Features
- Ruffle spaghetti straps
- Ruffle square neckline
- High waist seam
- Front slit
- Mid-length, flowy fit
- All over ditsy floral print
- Knit fabric | Moderate stretch
Style Number/Barcode: 05102-0455
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knits Not You Crossover Mini Dress
Can you handle knit? Because we can't! This fitted dress is more than a 9-5 piece! Style with a blazer, or long duster for the daytime, then once 5 hits ditch the blazer for ur happy hour attire!
Fit & Features
- Cross over neckline
- Sleeveless
- Form fitting silhouette
- Ribbed knit material
- Moderate stretch
- Mini hemline
Style Number/Barcode: 06005-0495
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Can't V Bothered Sweater Dress
Chilly? Never heard of her. Stay stylishly festive and warm in the form-flattering and heavy knit Can't V Bothered sweater dress.
Fits & Features
- V Neckline & Back With Surplice Design
- Roomy, Cuffed Dolman Sleeves
- Bar Strap Accent At Back
- Removable, Waist Tie
- Hem Hits Mid Thigh
- Comfortable Form-Fit I Ample Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
White & Blue: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0500
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feline Fierce Sweater Dress
Bold leopard spots and a live-in knit are a must-have combo for the chilly season. Stay stylish and warm in The Feline Fierce sweater dress!
Fits & Features
- Surplice Bodice With V Neck & Back
- Cuffed Long Sleeves
- Knit Composition With Leopard Inspired Print Throughout
- Includes Removable Waist Tie
- Bar Strap Accent At Back
- Mini Length Silhouette
- Form Hugging Fit I Ample Stretch
Brown: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Beige: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0489
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Long Sleeve Ribbed Mini Dress
Add this staple to your closet to create some seriously fab fall looks!
Fits & Features
- Turtleneck
- Long Sleeves
- Mini Silhouette
- Ribbed Knit
- Form Hugging Fit | Moderate Stretch
- No Zipper
Style Number/Barcode: 06005-0474
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off Shoulder Knit Mini Dress
There's no such thing as cold weather blues in this number. Snuggle up to this comfy and cute mini dress!
Fits & Features
- Wide, Off Shoulder Neckline
- Cuffed Quarter Length Sleeves
- Elastic Waistband
- Form-Hugging Silhouette I Moderate Stretch
- Knit Composition I Fully Lined At The Skirt
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0511
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Stunner Smocked Mini Dress
You'll be simply stunning in this floral smocked mini dress! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked hems, and a stretchy smocked dress with a short, mid-thigh length hem with a front drawstring to cinch.Style Number/Barcode: 05102-0510
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ready For It Mini Dress
Get ready to have a total trendy look with this cute little mini! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked cuffs, and a stretchy, smocked dress with a short, mid-thigh length hem with a front drawstring.Style Number/Barcode: 05102-0507
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance