Workwear Midi Dresses
Ready to rock the office runway, Windsor girl? Our collection of workwear midi dresses is here to take your 9-to-5 style game from drab to fab. Whether you're commanding the boardroom or owning that virtual meeting, these chic and versatile pieces are your secret weapon for making power moves with a side of sass. From sleek silhouettes to playful patterns, each dress is designed to keep you looking effortlessly polished while letting your personality shine through. So go ahead, strut your stuff and show them who's boss—because in these workwear midi dresses, you're unstoppable!
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$42.90
A sleek black knit midi dress with a cowl neckline, high slit, and fitted A-line silhouette.
$36.90
An elegant black off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$39.90
A captivating black floral mesh maxi dress with a lace-up back and flared hem.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched details, sheer sleeves, and a ruffled hem.
$59.90
A green satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$34.90
A plum floral midi dress with a strapless neckline and front slit in knit fabric.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: S | Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Light Blue | Size: L | Knit Fabric
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 & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: S | Knit Fabric
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric
Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory
$9.97 $30.90
68% off
Dainty floral makes this eyelet midi dress the cutest spring-to-summer style! Fit & FeaturesDainty floral print, eyelet fabric, sewn-in knit lining, Strapless neckline, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory | Size: XS | Knit Fabric
Workwear Midi Dresses
Workwear midi dresses are the ultimate power move for the girlboss who’s got meetings at nine and happy hour at five. These are the dresses you reach for when you want to look like you’ve got your life together—even if your coffee order is the only thing you’ve nailed down today. Midi workwear dresses hit that sweet spot: long enough to keep things polished for the boardroom, but with just enough sass to remind everyone you’re not here to blend in. Picture yourself strutting into the office, the hem of your dress swishing perfectly as you breeze past the water cooler—confidence on full display, not a care in the world. These dresses aren’t just about looking professional; they’re about feeling unstoppable, whether you’re presenting to the execs, running the show at your own start-up, or making your mark at your first internship.
Let’s be real: the right midi dress is more than just a wardrobe staple—it’s a whole vibe. You know you’ve found the one when it carries you from Monday’s back-to-back Zoom calls to Friday’s team lunch without missing a beat. Midi dresses Windsor girls love are all about versatility: think classic silhouettes with a twist, bold prints that show off your personality, and comfy-yet-chic fabrics that won’t cramp your style when you’re hustling through your day. They’re perfect for gifting too—because what’s better than giving your bestie, sister, or work wife a little extra confidence boost? Whether she’s starting a new job, celebrating a promotion, or just needs a reminder that she’s *that* girl, a midi workwear dress is a gift that says, “Go get ‘em, tiger.” And if you’re the one treating yourself (as you should), there’s no better feeling than slipping into a dress that fits like it was made for you, ready to take on whatever the day throws your way.
Don’t forget to play with your look—midi workwear dresses are a blank canvas for your personal style. Layer on a tailored blazer for those “I’m in charge” moments, or swap in a pair of chunky sneakers for a quick coffee run. Accessories? Go wild with statement earrings, a bold lip, or that oversized tote that fits your whole life. And if you’re building out your workwear wardrobe, don’t sleep on the power of mixing and matching. Pair your favorite midi dress with pieces from our Workwear Skirts collection for endless outfit inspo—because who says office style has to be boring? With midi dresses Windsor girls swear by, you’ll never have to choose between looking professional and feeling like your most confident, authentic self. You’re not just dressing for work—you’re dressing for the life you’re building, and trust us, you’re absolutely killing it.