Work Dresses & Outfits

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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Workwear Dresses for the Office, Conference, or Meeting

Refresh your work wardrobe with our latest collection of spring-ready workwear dresses, designed to keep you polished, comfortable, and effortlessly stylish. Whether you're heading into the office, attending an industry conference, or meeting clients over lunch, our work dresses offer the perfect balance of sophistication and versatility for a seamless day-to-night transition.

Embrace Light & Breezy Fabrics for Spring

This season, refresh your professional look with midi dresses in breezy chiffon, soft crepe, and lightweight knit—perfect for a polished yet effortless aesthetic. These midi styles elongate your silhouette while offering a refined below-the-knee length that’s ideal for your workday. Style a sleeveless midi dress with a tailored blazer and sleek point-toe heels for a crisp, professional ensemble.

Layer with Chic Spring Staples

As the season transitions, layer up with a lightweight cardigan over a fresh floral or abstract print dress and finish the look with classic block-heel sandals for a polished, feminine touch. For a modern business casual vibe, pair a ribbed knit midi dress with a structured denim jacket and neutral-toned mules for an effortless blend of comfort and sophistication. These midi-length work dresses from Windsor make everyday styling effortless.

From Work to After-Hours in Style

Knit and lightweight sweater dresses are perfect for both the nine-to-five grind and after-work plans. These versatile pieces can take you from your desk to dinner with ease—simply swap out your blazer for a sleek faux leather moto jacket and add statement earrings for a polished evening look.

Step into spring with confidence in Windsor’s latest collection of workwear dresses that keep you looking chic and professional. Discover the newest styles 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.

  • Effortlessly Stylish Linen Dress

    You'll look effortlessly stylish this season in this lightweight and flowy linen dress! Designed with a breezy woven fabric, this short dress is perfect for your summer parties. The bodice is shaped with a square neckline with ruching at the bust and long balloon sleeves. The fitted waistband creates a cinched silhouette, flowing out to a short ruffled hem with an A-line fit for a pretty flair. Complete the look with clear heels.

    Fit & Features

    • Linen woven fabric, no stretch
    • Square neckline, ruched bust
    • Long balloon sleeves, elastic cinched hems
    • Front waistband, back zipper closure
    • Ruffled hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-4246

    Category Name: Work Dresses & Outfits

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Memorable Vibe Strapless Plaid Pleated Mini Dress

    A strapless plaid mini dress features a form-hugging fit with a sassy pleated hem. Perfect for back-to-school styling.

    Fit & Features

    • Plaid print, woven fabric, slight stretch
    • Strapless folded neckline
    • Back zipper closure
    • Form-hugging fit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5862

    Category Name: Work Dresses & Outfits

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweeter Than Pie Scoop Neck Gingham Mini Dress

    So on trend and sweeter than pie, this gingham mini dress is essential for spring-to-summer fun! This mini-length dress is made from woven fabric and features a charming gingham print that exudes effortless style.  The scoop neckline and tank shoulder straps flatter your figure, while the form-hugging fit accentuates your curves. Complete the look in cute sandals and a mini purse!

    Fit & Features

    • Gingham print, woven fabric, slight stretch
    • Back zipper closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5568

    Category Name: Work Dresses & Outfits

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Masterpiece Short Sleeve Marble Midi Dress

    Your look will be a modern masterpiece in this marble print mesh midi dress - a stunning piece for art gallery openings or cocktail parties! The airy sheer mesh fabric is lined with a stretchy knit for comfortable wear. The short sleeves and crew neckline create a classic look, while the bodycon silhouette accentuates your curves down to the midi-length hem with a back slit for movement. Complete the look with a purse and strappy stiletto heels.

    Fit & Features

    • Marble print
    • Sheer mesh fabric lined with stretchy knit
    • Crew neckline
    • Short sleeves
    • Bodycon silhouette
    • Back slit
    • Runs true to size

    Style Number/Barcode: 05102-5535

    Category Name: Work Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Style Long Sleeve Ribbed Knit Midi Dress

    The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.

    Fit & Features

    • Hacci ribbed knit fabric, plenty of stretch
    • V-neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5920

    Category Name: Work Dresses & Outfits

    Price: $38.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

  • Effortless Beauty Floral Mini Dress

    Radiate effortless beauty in this gorg floral mini dress! It features a square neckline, sheer long peasant sleeves to add a chic flair, all-over ruching, a mini-length hem with a form-hugging fit, and an all-over blooming floral print. The sheer chiffon fabric includes a partial knit lining down the body of the dress. Style with dainty duster earrings and a pair of neutral heels.

    Fit & Features

    • Square neckline
    • Sheer long peasant sleeves, elastic cinched hems
    • All-over ruching, back zipper, hook and eye closure
    • Mini-length hem, form-hugging fit
    • Floral print
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1860

    Category Name: Work Dresses & Outfits

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work It Girl Scoop Neck Ponte Short Dress

    Work it, girl, in this ponte short dress in the office or at networking events! With its cap sleeves, scoop neckline, and bodycon silhouette, it flatters your figure and hugs your curves in all the right places while the center back slit offers movement. Pair with sleek pumps and minimal jewelry for a polished and poised look!

    Fit & Features

    • Smooth ponte knit fabric with stretch
    • Back zipper and hook-eye closure
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3271

    Category Name: Work Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Knit Off-The-Shoulder A-Line Mini Dress

    Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!

    Fit & Features

    • Soft ribbed knit fabric
    • Off-the-shoulder straight neckline, fold-over design
    • Long fitted sleeves
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5892

    Category Name: Work Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: HEATHERGRAY

    Available Size: XS, S, M, L

  • That Classic And Chic Vibe Ruched Midi Dress

    This sexy ruched midi dress will give you that classic and chic vibe! It features a flattering one-shoulder neckline and a mid-length, form-hugging fit with ruched detailing to enhance your curves. The double-lined knit fabric offers plenty of stretch. Pair this midi dress with duster earrings to level up the look.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Mid-length, form-hugging fit
    • Ruched detailing
    • Double-lined knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-0919

    Category Name: Work Dresses & Outfits

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Knit Mini Dress

    This trendy ruched knit mini dress will have your everyday 'fits always on point! Made with a stretchy ribbed knit fabric for comfortable wear, this mini-length dress features a sleeveless scoop neckline with thin tank shoulder straps and ruched detailing to accentuate your curves on the bodycon silhouette. Style with a boyfriend blazer and heels for happy hour!

    Fit & Features

    • Stretchy ribbed knit fabric lined with knit
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5569

    Category Name: Work Dresses & Outfits

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

  • Trendy Element Turtleneck Long Sleeve Mini Dress

    Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!

    Fit & Features

    • Double-lined ribbed knit fabric, moderate stretch
    • Fitted long sleeves
    • Folded turtleneck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5245

    Category Name: Work Dresses & Outfits

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Swirls Of Attraction Strappy Marble Print Midi Dress

    Attract all the attention when you step out in this marble print midi dress for dinner and drinks! It features a sleeveless scoop neckline, spaghetti straps, an open strappy back design, a bodycon silhouette, and a flattering side ruched seam and slit along the asymmetrical hem. Complete the look with a fab earrings set and heels.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Open strappy back design
    • Bodycon silhouette
    • Side ruched seam and slit
    • Asymmetrical midi-length hem
    • Marble print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5259

    Category Name: Work Dresses & Outfits

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Beauty Sleeveless A-Line Mini Dress

    This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5631

    Category Name: Work Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Silhouette Abstract Print Mesh Midi Dress

    Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.

    Fit & Features

    • Abstract printed sheer mesh fabric, plenty of stretch
    • Mock neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Full-length knit lining, scoop neckline, adjustable spaghetti straps
    • Runs true to size

    Style Number/Barcode: 05102-5879

    Category Name: Work Dresses & Outfits

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

  • Basic Essential Ribbed Knit Midi Dress

    This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Form-hugging fit
    • Side slit, midi-length hem
    • Double-lined rib knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4961

    Category Name: Work Dresses & Outfits

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

  • Sweet Harmony Chiffon Midi Dress

    Your sweet style personality goes in harmony with this chiffon midi dress perfect for any upcoming weddings and parties! The knee-length dress features short puff sleeves, a sweetheart neckline, princess seams, and a front flirty slit along the A-line silhouette. Pair with a chic ring set and heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Princess seams, front slit, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Airy chiffon fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1850

    Category Name: Work Dresses & Outfits

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful View Collared Scenic Waist Skater Dress

    You'll be such a delightful view in this collared skater dress strolling the streets of Silicy or downtown! Featuring long sleeves with buttoned cuffs and a collared V-neckline, hidden front hook and eye fasteners provide a seamless look, and a scenic printed waist and short skater silhouette add a touch of charm. Complete the look in heels and a crossbody purse.

    Fit & Features

    • Gauze woven fabric with lining, no stretch
    • Collared V-neckline
    • Hidden front hook and eye fasteners
    • Scenic printed waist
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5638

    Category Name: Work Dresses & Outfits

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Girl Energy Houndstooth Knit Mini Dress

    Bring the chic girl energy to your fall wardrobe with this trendy mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, and a bodycon silhouette to showcase your curves. The knit fabric features an all-over houndstooth pattern for an elevated vibe. Style this mini dress with a faux leather moto jacket and combat boots!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length hem
    • Bodycon silhouette
    • Houndstooth pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5410

    Category Name: Work Dresses & Outfits

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Marble Sleeveless Mesh Midi Dress

    A sleeveless abstract marble print mesh midi dress features a sleek crew neckline, a flattering form-hugging fit, and a flirty side slit. Pair with heels.

    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: Work Dresses & Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: CHARCOAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • 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: Work Dresses & Outfits

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: Work Dresses & Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • 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: Work Dresses & Outfits

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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: Work Dresses & Outfits

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

  • 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: Work Dresses & Outfits

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale