Workwear Dresses
Elevate your professional wardrobe with our sophisticated collection of work dresses, perfect for speaking presentations to business casual days. Our selection is tailored to meet the demands of the modern workplace, ensuring you find the ideal dress to showcase your style and professionalism. Opt for a refined crepe midi dress that exudes elegance and grace, ideal for important meetings or a day at the office. For a more contemporary twist, explore our sweater dresses, blending classic style with modern comfort. Whether you're presenting in the boardroom or networking at a business luncheon, our work dresses are designed to make a statement, balancing the perfect blend of sophistication, functionality, and style
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MOST POPULARFall Workwear Dresses for the Office, Conference, or Meeting
Refresh your fall wardrobe with our latest workwear dresses, designed to elevate your professional style while keeping you cozy as the temperatures drop. Perfect for office days, industry conferences, or after-hours events, our work dresses combine style, comfort, and versatility to ensure you're ready for anything the day brings.
This season, embrace the chic 2024 trends with midi dresses in ribbed sweater knit and woven crepe—ideal for creating an elegant, tailored look. These midi styles not only elongate your silhouette but also provide a polished below-the-knee length that’s perfect for your workday. Pair a sleeveless midi dress with a tailored blazer and classic point-toe heels for a sharp, professional ensemble.
As fall settles in, layer up with a cozy cardigan over a dark floral or abstract print dress and finish the look with tall boots for a stylish boho-inspired outfit. For a business casual vibe, consider a ribbed knit midi dress teamed with a denim jacket and ankle booties, striking the perfect balance between comfort and polish. These midi-length work dresses from Windsor are a must-have for easy, everyday styling.
Knit and sweater dresses are your go-to choices for both the nine-to-five grind and any work-related events. These all-in-one ensembles are versatile enough to transition from day to night—just swap your blazer for a faux leather moto jacket before heading to happy hour or a client dinner.
Prepare to make power moves this fall with our collection of workwear dresses that will keep you looking effortlessly chic and professional. Explore our latest arrivals now and start curating your perfect 2024 fall work wardrobe. Shop online or visit your nearest Windsor store today!
How can I style a dress for work?
You can style your work dresses with layers, statement and minimal jewelry, and chic footwear. Starting with layers, you can layer your workwear dress with structured or boyfriend blazers to elevate your business casual look. You can style your blazer by rolling the sleeves up to a quarter length, then adorn your look with dainty chain link bracelets. For your sleeveless dresses that may not be work-appropriate when worn alone, you can style these dresses with long sleeve tops or collared blouses underneath to refresh your sleeveless dresses for work. Another chic layering option could be styling your tie-front tops over your sleeveless or strapless dresses. Be sure to choose a pattern that compliments your dress. Avoid clashing by pairing prints with muted colors to create a seamless contrast that goes together. Be sure to add accessories like statement necklaces, dainty chain-link necklaces, versatile hoops, and studs that elevate your workwear outfits. For your footwear, you can style your dress with sturdy mules, block heels, or ankle booties that are comfortable enough to wear all day but give your dresses a stylish feel—avoid wedges and sandals that may be deemed too casual for the workplace.
How do I know if my dress is ok to wear at work?
The best way to know if your dress is ok to wear at work is to consult your employee handbook to gauge whether your outfit is in line with the dress code. Now if your handbook isn’t explicitly clear on the dress code, a good rule of thumb would be to dress business casual or err on the side of classic and accessible. For the fabrication choose dresses that come in durable fabrications like ribbed knit, Ponte knit, and crepe—avoid sheer fabrics that can reveal more than you’d like to at work. For example, it’s best to not have any spaghetti straps, strapless styles, or halter dresses without another layer. That’s where sweaters and blazers as layering pieces come in handy to make sure your dress is work-appropriate. In addition, you should also think about the length of your dress and how tight it is. If it seems more club-appropriate than work-appropriate, it’s best to leave it at home and reach for a classic shift dress instead. The bottom line is that you want to look professional in all that you do in your career or that part-time gig, and wearing a work-appropriate dress sends just that message.
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Abstract Marble Sleeveless Mesh Midi Dress
Fit & Features
- Abstract marble printed sheer mesh fabric with brushed knit lining, plenty of stretch
- Sleeveless crew neckline
- Tank shoulder straps
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5869
Category Name: Workwear Dresses
Price: $39.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, S, M, L
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Another Day Long Sleeve Sweater Midi Dress
Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Soft, stretchy sweater rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5305
Category Name: Workwear Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Flair Plaid Woven Bubble Hem Skater Dress
Add some flair to your fall 'fits in this chic skater dress designed with a plaid printed cotton woven fabric. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a trendy V-shaped waist, and a short skater silhouette with the cutest bubble hem.
Fit & Features
- Plaid cotton woven fabric with knit lining, minimal stretch
- Square neckline
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- V-shaped waist
- Short skater silhouette, bubble hem
- Runs true to size
Style Number/Barcode: 05102-5870
Category Name: Workwear Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Side Effect Sweater Knit Dress
The side effects of wearing this sweater mini dress may cause many compliments! It features a sleeveless, square neck, thin tank-style straps, side cutouts with chain-link detail, and a bodycon silhouette. Complete the look in large hoop earrings.
Fit & Features
- Sleeveless, square neck, thin tank-style straps
- Side cutouts, chain-link detail
- Bodycon silhouette
- Mini-length hem
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1271
Category Name: Workwear Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sheer Exellence Mock Neck Bodycon Mesh Midi Dress
Experience sheer excellence in this stunning mesh midi dress perfect for dinners downtown or concerts. The sheer short sleeves and mock neckline add a touch of chic, while the bodycon silhouette flatters your figure. The sheer mesh fabric and smooth knit slip provide a luxurious feel, and adjustable spaghetti straps ensure a perfect fit. Complete the look with this midi dress in block heels and a hair clip for a fashion-forward style!
Fit & Features
- Sheer mesh fabric
- Includes a smooth knit slip, adjustable spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5540
Category Name: Workwear Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Weekend Chic Satin V-Neck Slip Dress
Keep it chic this weekend in this satin slip dress for a classy night out! It features a sleeveless V-neckline, adjustable spaghetti straps, and a short-length hem. Complete the look in the matching tunic.
Shop Matching Tunic: Weekend Chic Satin Button-Front Tunic
Fit & Features
- Sleeveless
- V-neckline
- Adjustable spaghetti straps
- Short-length hem
- Satin knit fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1612
Category Name: Workwear Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Sleeveless Knit Mini Dress
Look and feel pretty in this plaid mini dress, which boasts a flirty V-neckline and bodycon silhouette that shows your curves! Pair with a leather jacket and flats.
Fit & Features
- Woven knit fabrication
- Sleeveless v-neckline
- Spaghetti straps
- Plaid print
- Side slit
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5930
Category Name: Workwear Dresses
Price: $26.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M
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Floral Fever Ribbed Knit Mini Dress
Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Tie-front
- Ditsy floral print
- Mini-length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2032
Category Name: Workwear Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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RSVP To Cute Ditsy Wildflower Tie A-Line Midi Dress
RSVP yes to shower or birthday invites when you have this cute ditsy wildflower tie A-line midi dress in your closet! Embellished with a ditsy wildflower print, this midi-length dress is sure to turn heads. With short puff sleeves and a square neckline, this dress is perfect for casual-dressy occasions. The tie front bust adds a touch of whimsy while the a-line silhouette and front slit provide movement and a flattering look. Complete the look with luxe earrings and tennis shoes.
Fit & Features
- Ditsy wildflower print
- Woven fabric lined with stretchy knit
- Tie front bust, back zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3008
Category Name: Workwear Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh Lines Sleeveless Pinstripe Mini Tube Dress
Look fresh this season in this strapless pinstripe mini dress boasting a sleek bodycon silhouette and faux front pockets. Pair with chic flats.
Fit & Features
- Woven knit fabrication
- Sleeveless square neckline
- Pinstripe pattern
- Faux front pockets
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5963
Category Name: Workwear Dresses
Price: $32.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Wild And Chic Zebra Print Mini Sweater Dress
Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.
Fit & Features
- Sleeveless V-neckline
- Halter straps, tie-back design
- Open back
- Mini-length hem
- Curve-hugging silhouette
- Zebra print, sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1699
Category Name: Workwear Dresses
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Chic Icon Long Sleeve Knit Midi Dress
Become an instant chic icon in this bodycon midi dress adorned with flare cuff long sleeves with flirty tie accents and a V-neckline. Pair with mules.
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5895
Category Name: Workwear Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Feeling Good Turtleneck Maxi Dress
Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.
Fit & Features
- Long fitted sleeves
- Turtleneck
- Form-hugging silhouette
- Side slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4861
Category Name: Workwear Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute In The City V-Neck Knit Midi Dress
You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.
Fit & Features
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Bell long sleeves
- Front and back V-neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5888
Category Name: Workwear Dresses
Price: $33.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Best Seller
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Workwear Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch Date Floral Chiffon Skater Dress
This adorable floral chiffon skater dress is perfect for brunch dates! The mini dress features a sleeveless square neckline, spaghetti straps, a smocked bust, a short skater skirt with a fit and flare silhouette, and a dainty floral print pattern, this dress is a must-have for the spring and summer seasons. Style with heeled sandals.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Smocked bust
- Short skater skirt, fit and flare silhouette
- Dainty floral print
- Swiss dot chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2282
Category Name: Workwear Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Workwear Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Basics Ribbed Knit Midi Dress
Fit & Features
- Ribbed knit fabric with brushed knit lining, plenty of stretch
- Crew neckline
- Short sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5603
Category Name: Workwear Dresses
Price: $28.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, M, L
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Irresistible Romance Rose Velvet Lace Midi Dress
Who can resist your romantic allure in this rose velvet midi dress? It features a sleeveless sweetheart neckline with a sheer lace trim, sleek bungee spaghetti straps, a curved underbust seam, a bodycon silhouette, and a back-slit accent. The mid-length dress is composed of a flocked velvet rose pattern on sheer mesh fabric with a stretchy knit lining. Complete the look in chic stiletto mules for a cocktail party or rehearsal dinner!
Fit & Features
- Sleeveless sweetheart neckline, sheer lace trim
- Bungee spaghetti straps
- Curved underbust seam
- Bodycon silhouette
- Midi-length hem, back slit accent
- Rose flocked velvet pattern, sheer mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3218
Category Name: Workwear Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY, TAUPE, SAGE, BURGUNDY
Available Size: XS, S, M, L, XL
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Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Workwear Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Mood Collared Woven Skater Dress
Charm them all with your chic style in this sleeveless collared skater dress! Designed with a lightweight woven fabric, this short dress features a collared V-neckline and a flirty open back. The button-front design goes down the complete length of the dress for effortless styling. The high waist is accented with a wide belt for a cinched look, leading to the fit and flare skater silhouette. Complete the look for a spring party with clear heels.
Fit & Features
- Non-stretch lined woven fabric
- Sleeveless collared V-neckline, open back
- Button-down front
- High belted waist with circular buckle
- Skater silhouette
- Sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-3346
Category Name: Workwear Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Vibes Collared Striped Woven Skater Dress
Sweet and stylish, this striped woven skater dress is spring-time perfection! The lightweight woven fabric features a chic vertical striped pattern for a polished look. The short dress has a collared V-neckline for that touch of sophistication, leading to a partial button-down front. The short puff sleeves add an adorable detail. The high waist is accented with a tie-back design, and flows out to a fit-and-flare skater silhouette. Pair this short dress with wedges for weekend brunch!
Fit & Features
- Non-stretch cotton-blend woven fabric, woven skirt lining
- Vertical striped pattern
- Collared V-neckline, button-down front
- Short puff sleeves with elastic cinched hems
- High waist with back elastic band, tie-back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5657
Category Name: Workwear Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Era Drop Waist A-Line Mini Dress
Enter your trendy era with this woven mini dress featuring a sleeveless square neckline and a halter strap accented with a buckle trim detail. The drop waist design leads to a short pleated A-line silhouette.
Fit & Features
- Woven fabric
- Square neckline
- Halter strap with buckle trim detail
- Partially open back, zipper closure
- Drop waist design
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5974
Category Name: Workwear Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: CHARCOAL
Available Size: S, M, L
Product Badge:- Sale
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Perfect And Stylish Scoop Neck Ribbed Knit Midi Dress
Perfect and stylish for everyday occasions, this basic ribbed knit midi dress is just what you need for coffee dates, shopping downtown, or grabbing dinner with friends! This stunning dress features classic short sleeves, a flattering scoop neckline, and a bodycon silhouette for a sleek curve-flaunting appeal. The side slit offers movement along the mid-length hem, while the soft and stretchy ribbed knit fabric ensures all-day comfort. Style this midi dress with a casual jacket, sandals, and a crossbody bag to complete the look!
Fit & Features
- Soft, stretchy ribbed knit fabric
- Side slit
- Bodycon silhouette
- Midi-length
- Runs true to size
Style Number/Barcode: 05102-5554
Category Name: Workwear Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale