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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Fall 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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Sharp Lines Asymmetrical Long Sleeve Midi Dress
Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look!
Fit & Features
- Ribbed knit fabrication
- Asymmetrical off-the-shoulder neckline
- Pleated popover accent at the neckline
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5947
Category Name: Workwear Dresses
Price: $46.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L, XL
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Sleek Vibes Long Sleeve Ruched Midi Dress
Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour!
Fit & Features
- Smooth knit fabrication
- Boat neckline
- Long sleeves with thumb holes
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3954
Category Name: Workwear Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Elevated Button-Down Drop Waist Mini Dress
So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.
Fit & Features
- Textured knit fabric, sewn-in knit lining
- Square neckline
- Tank shoulder straps
- Button-down front
- Drop waist
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3842
Category Name: Workwear Dresses
Price: $36.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Note To Self Ribbed Knit A-Line Mini Dress
Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.
Fit & Features
- Soft and stretchy ribbed knit fabric
- Crew neckline
- Tank shoulder straps
- Front slit
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5632
Category Name: Workwear Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Vibes Off The Shoulder Knit Midi Dress
Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch!
Fit & Features
- Lined ribbed knit fabrication
- V-neckline and off-the-shoulder
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5942
Category Name: Workwear Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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Cosmic Chic Tie-Dye Knit Midi Dress
The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe.
Fit & Features
- Ribbed knit fabrication
- Scoop neckline
- Long sleeves
- Tie-dye pattern
- Center slit at back of hem
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2132
Category Name: Workwear Dresses
Price: $54.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Adorable Stunner Strapless A-Line Mini Dress
You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.
Fit & Features
- Crepe fabric, stretchy knit lining
- Contrast color block outline
- Strapless straight neckline
- High waist seam
- Back zipper closure
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3801
Category Name: Workwear Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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All Things Cozy High Slit Knit Midi Dress
Oh-so-cute and cozy, this knit midi dress is a seasonal staple. It features a mock neckline, long fitted sleeves, an asymmetric mid-length hem creating a thigh-high side slit, and a form-hugging silhouette. The ribbed hacci knit fabric has an ultra-soft feel with plenty of stretch. Style this midi dress with knee-high boots for a latte date.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Asymmetric mid-length hem
- Thigh-high side slit
- Form-hugging fit
- Ribbed hacci knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5333
Category Name: Workwear Dresses
Price: $24.90
Availability: In Stock
Available Color: COGNAC
Available Size: XS, S, M, L
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Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress
Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5894
Category Name: Workwear Dresses
Price: $36.90
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: XS, S, M, L
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Adorable Look Plaid Print Strapless Skater Dress
Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.
Fit & Features
- Plaid printed woven fabric
- Strapless sweetheart neckline
- Back zipper closure
- Drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5925
Category Name: Workwear Dresses
Price: $46.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Preppy Posh Strapless A-Line Pleated Mini Dress
Look fabulously mod with this strapless mini dress! Made from smooth woven fabric, discover a next-level fashionista vibe in this dress featuring an A-line silhouette, belt loop accents along the waist, and a pleated mini-length hem for added flair. Complete the look in a blazer for weekend plans!
Fit & Features
- Strapless neckline
- A-line silhouette
- Belt loop accents along the waist
- Pleated mini-length hem
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5444
Category Name: Workwear Dresses
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
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Flawless Allure Crepe Tube Mini Dress
Keep it flawless in a mini dress that features a sleeveless square neckline and faux front pockets with trendy flap closure. Complete look with a blazer for the perfect workwear outfit.
Fit & Features
- Woven crepe fabrication, moderate stretch, stretchy knit lining
- Sleeveless square neckline
- Faux front pockets with flap closure
- Mini length hem
- Runs true to size
Style Number/Barcode: 05101-3811
Category Name: Workwear Dresses
Price: $42.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Chic Staple Ribbed Knit Skater Dress
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over accent
- Long fitted sleeves
- Short-length hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06005-2070
Category Name: Workwear Dresses
Price: $36.90
Availability: In Stock
Available Color: OATMEAL, HUNTER, HEATHERGRAY, PINK
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Fabulous Icon Sleeveless Ribbed Knit Midi Dress
An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.
Fit & Features
- Soft, stretchy ribbed knit fabric
- Square neckline
- Underbust seam
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-1853
Category Name: Workwear Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serving Sleek Square Neck Bodycon Midi Dress
Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels.
Fit & Features
- Brushed knit fabric with knit lining, plenty of stretch
- Square neckline
- Thin tank shoulder straps
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5975
Category Name: Workwear Dresses
Price: $39.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: M, L
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Fresh Breeze Floral Chiffon Midi Dress
Freshen up your wardrobe for spring to summer with this floral chiffon midi dress - a lovely style for wedding showers and birthday brunches! It features adorable puff short sleeves, a square neck, a flirty bust tie and underbust seam detail, and a slim-fit silhouette with a front slit hem. The airy chiffon fabric features a bouquet floral print pattern. Complete the look with dainty hoop earrings.
Fit & Features
- Puff short sleeves, elastic cinched hems
- Square neck, bust tie, underbust seam detail
- Back zipper, hook and eye closure
- Slim-fit silhouette, front slit, midi-length hem
- Bouquet floral print
- Sheer chiffon fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2130
Category Name: Workwear Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Long Sleeve Midi Dress
Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline, foldover accent
- Long sleeves
- Snap button accents at the hem
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2108
Category Name: Workwear Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK, PLUM, RED
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Striped Delight Surplice Collared Mini Dress
You're sure to have a day full of sweetness in this delightful striped mini dress perfect for upcoming weekend plans! This dress is designed with chic long sleeves with button cuffs, along with a flattering collar V-neckline and wrap tie waist belt for that cinched look. The surplice mini-length hem adds a touch of sass while the pleated form-hugging fit accentuates your curves. Complete the look in clear sandals and earrings.
Fit & Features
- Striped non-stretch woven lightweight fabric
- Collared V-neckline
- Long sleeves with buttoned cuffs
- Wrap tie waist belt with pleating
- Surplice mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5610
Category Name: Workwear Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Chic Season Mock Neck Cutout Ribbed Knit Mini Dress
Comfy meets chic in this adorable ribbed knit mini dress featuring a mock neckline, long fitted sleeves, a bold cutout above the bust, and a short bodycon silhouette. Style with knee-high boots.
Fit & Features
- Ribbed knit fabric with moderate stretch
- Mock neckline
- Long fitted sleeves
- Cutout above the bust
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2091
Category Name: Workwear Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: XS, S, M, L
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She's The Main Rib Knit Strapless Midi Dress
Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!
Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Fitted midi-length hem
- Soft and stretchy
- Rib knit fabric, short knit lining
- Runs true to size
Style Number/Barcode: 05102-5872
Category Name: Workwear Dresses
Price: $33.90
Availability: In Stock
Available Color: GRAY, IVORY, SAGE, BROWN-2
Available Size: XS, S, M, L, XL
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Basic Bae Square Neck Tank Sweater Mini Dress
Fall for this basic sweater mini dress to meet all of your day-to-night fashion needs! Crafted from a luxe rib knit fabric with the perfect amount of stretch, this short dress is designed to fit your body like a glove. Featuring a classic square neckline for a show of skin, comfortable tank shoulder straps, and a bodycon silhouette that'll turn heads! Style this mini dress with strappy heels to elevate your look.
Fit & Features
- Sweater rib knit fabric with stretch
- Tank shoulder straps
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-1838
Category Name: Workwear Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Draw The Line Striped Sweater Midi Dress
Draw the line at basic and reach for this sensational striped sweater dress! It features a trendy off-the-shoulder neckline, fitted long sleeves, a flattering bodycon silhouette, and dual tie-back closures, and a cutout design. Complete the look with a chic crossbody bag for day or evening plans.
Fit & Features
- Off-the-shoulder neckline
- Fitted long sleeves
- Dual tie-back closures, cutout design
- Bodycon silhouette
- Midi-length hem
- Striped pattern, stretchy sweater knit fabric
- Runs true to size
Style Number/Barcode: 05102-5360
Category Name: Workwear Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
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Toasty Sweetheart V-Neck Bodycon Knit Midi Dress
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- Front slit
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2065
Category Name: Workwear Dresses
Price: $38.90
Availability: In Stock
Available Color: NATURAL, RUST, MAUVE, OLIVE
Available Size: S, M, L, XS
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Casual Chills Long Sleeve Slit Mini Dress
Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!
Fit & Features
- Bell long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit, mini-length hem
- Rib knit fabric
- Minimal stretch
- Please be advised this dress runs one size small
Style Number/Barcode: 05102-5871
Category Name: Workwear Dresses
Price: $24.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Best Seller