Day Date Outfits
Day date outfits are all about serving main character energy from morning coffee runs to spontaneous adventures. Whether you’re vibing with a flirty skirt or keeping it chill with a cute top and jeans, these looks are made for catching eyes and making memories. Your outfit should match your mood—playful, confident, and ready for whatever the day throws your way. So go ahead, let your style do the flirting and turn every “just hanging out” into an unforgettable story.
$89.90
A yellow mini dress with faux pearl embellishments, halter cowl neck, and bodycon fit.
$49.90
A black sheer midi dress with off-the-shoulder neckline, plunging v-neck, and high-side slit.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$46.90
A black halter pleated romper with a form-hugging bodice and mini-length hem.
$32.90
An airy white woven crop top featuring long bell sleeves and a flirty tie-front closure.
$36.90
A yellow eyelet lace bustier with a sweetheart neckline and ruffled crop hem for flirty outings.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$46.90
A black floral midi dress with a sweetheart halter neckline and flowy A-line silhouette.
$32.90
A playful light blue cotton mini skirt featuring a pinstriped print and flouncy bubble hem.
$32.90
An ivory halter crop top featuring gingham ribbon trim, smocked back, and a fitted woven knit design.
$44.90
A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.
$49.90
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$36.90
A denim satin mini dress with a ruched wrap silhouette and sleeveless square neckline.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$42.90
A sleek black knit midi dress with a high front slit and sleeveless cowl neckline.
$38.90
A natural lace bustier with rhinestones and sequins, featuring padded cups and adjustable straps.
$39.90
A sultry black formal dress with rhinestone straps, a high slit, and a curve-hugging silhouette.
$34.90
A chic beige mesh crop top with ruched details, off-the-shoulder neckline, and tie sleeves.
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and halter neck design.
$39.90
A chic white glitter lace bodycon dress with adjustable straps and an asymmetric hem.
$35.90
A sage bodycon mini dress with a pleated cowl neckline and stretchy knit fabric.
$69.90
A white bodycon mini dress adorned with iridescent rhinestones and faux pearl embellishments.
$46.90
A stunning black knit romper adorned with rhinestones, featuring a strapless neckline and form-hugging silhouette.
$38.90
A red knit mini dress with a sleeveless square neckline, pleated bust, and A-line silhouette.
$19.97 $44.90 56% off
A pink floral mesh corset mini dress with a sweetheart neckline and adjustable spaghetti straps.
$69.90
A bold black mesh mini dress with studded rhinestones, ruching, and sheer long sleeves.
$24.90
A sleek off-white knit mini skirt featuring a high-rise waist, ruched sides, and ruffled hem.
$89.90
A black bodycon dress with faux pearl and beaded accents, featuring sheer sleeves and a wrap hem.
$14.97 $54.90 73% off
A chic black crepe formal dress featuring waist cutouts and a high side slit for allure.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$64.90
An elegant black velvet skater dress with an off-the-shoulder neckline and drop-waist design.
$59.90
A green satin off-the-shoulder midi dress with a sweetheart neckline and ruched wrap design.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$24.90
A smooth off-white knit crop top featuring a V-neckline, tie front, and moderate stretch.
$19.90
A breezy orange woven crop top featuring flowy short sleeves and a chic tie-front design.
$59.90
An ivory jumpsuit with faux pearl embellishments, sweetheart neckline, and wide-leg silhouette for elegance.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$54.90
An ivory satin skater dress with a halter neckline, drop waist, and bubble hem for semi-formal events.
$59.90
A navy blue velvet mermaid dress with a floral pattern, sleeveless cowl neckline, and high-side slit.
$49.90
A white woven knit mini dress featuring a sleeveless V-neckline and a flared A-line silhouette.
$29.90
A black knit mini skort featuring a belted wrap-front design and hidden fitted shorts for comfort.
$69.90
A shimmering green mermaid dress with an off-the-shoulder neckline and sheer ruched long sleeves.
$34.90
An olive green twill skort featuring a belted mid-rise waist, bodycon fit, and four-pocket styling.
$9.97 $49.90 80% off
A black velvet mini dress with a twist accent, open back, and chic side slit.
$64.90
A black velvet mermaid dress with glitter, corset bodice, and adjustable spaghetti straps.
$42.90
A black crepe mini dress featuring a sleeveless square neckline and faux flap pockets for modern flair.
$9.97 $44.90 78% off
A black velvet mini dress with a one-shoulder neckline and wrap-around waist cutout.
$24.90
A white ribbed knit crop top with cap sleeves, lace trim, and dual tie-front closures.
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The Marissa long satin dress brings elegance and sultriness to your formal night. The floor-length gown enhances your curves with a fitted bodice and flattering A-line silhouette while the high front slit provides movement. Fit & FeaturesStretch-satin fabric, non-see-through, double-lined bust, Sleeveless pleated cowl neckline, spaghetti straps, Slim-fit bodice, empire waistline, High front slit, floor-length hem, A-line silhouette, Runs true to size, Where to Wear:Prom, weddings, black-tie soirees, special date nights, and engagement parties. Free Shipping on All Orders Over $75. | Windsor Marissa Formal Satin Cowl Neck Dress in Green | Size: S | Satin Fabric
Shine bright and sparkle up the night in the gorgeous Leila mini dress. The dress boasts an alluring open back with a lace-up strappy design for a customized fit, and a short, curve-hugging silhouette. Shop Long Version: Kailani Formal Sequin Slit Mermaid DressFit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Sequin embroidery, scroll pattern, Sleeveless square neckline, adjustable spaghetti straps, Open back, lace-up strappy design, tie closure, High waist seam, lower back zipper, hook and eye closure, Mini-length hem, fitted bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, Vegas weekends, date nights Free Shipping on All Orders Over $75. | Windsor Leila Sequin Bodycon Mini Dress in Royal Blue | Size: XL | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Red | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric
Every occasion is worth celebrating in this off-the-shoulder midi dress! The smooth and stretchy knit fabric includes a full-length knit lining for additional coverage. The off-the-shoulder neckline and short-sleeve cuffs add a touch of elegance, while the bodycon silhouette and flared midi-length hem accentuate your curves in all the right places. Complete the look with teardrop earrings and heels. Fit & FeaturesSmooth stretchy knit fabric with knit lining, Off-the-shoulder neckline, Short-sleeve cuffs, Bodycon fit, Flare hem, Style runs small, Free Shipping on All Orders Over $75. | Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Natural | Size: XS | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: XL | Knit Fabric
Show up and stun this formal season in the gorgeous Brynlee bodycon mini dress! She features a sleeveless square neckline, a built-in padded bust, halter spaghetti straps, an open back with a lace-up design for a customized fit, and a short, curve-hugging silhouette. The lined mesh fabric features all-over sequin embroidery in an intricate scroll pattern. Style the formal mini dress with clear heels for a night to remember. Fit & FeaturesSleeveless, square neckline, Built-in padded bust, no bra required, Halter spaghetti straps, back button closure, Open back, lace-up design, zipper closure, Bodycon silhouette, mini-length hem, Sequin scroll embroidery, mesh fabric, knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
A mini dress that brings the luxe sensation! The Keira faux pearl short dress is a stunning style with a strappy tie-back design and a bodycon silhouette that highlights your figure. Fit & FeaturesLightweight mesh fabric, stretchy knit lining, Faux pearl and bead embellishments, Sleeveless cowl neckline, Spaghetti straps, strappy tie-back design, open-back, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Prom, birthday parties, bachelorettes, Vegas weekends, rooftop cocktails Free Shipping on All Orders Over $75. | Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Light Blue-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XL | Knit Fabric
Everyone will see you shining at the club in this glitter mini dress! It features an off-the-shoulder sweetheart neckline, sheer fitted ruched long sleeves, adjustable spaghetti straps, a ruched seam along the padded bust, a sheer bodice with trim, and side ruched seams that hug your curves on the bodycon silhouette. Complete the look with a clutch and heels. Fit & FeaturesOff-the-shoulder sweetheart neckline, Adjustable spaghetti straps, Sheer fitted ruched long sleeves, Ruched and padded bust, sheer bodice, trim, Side ruched seams, bodycon silhouette, mini-length hem, Glitter mesh fabric, sewn-in knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor See Me Shining Glitter Off-The-Shoulder Mini Dress in Wine | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Both sexy and demure, the Kristen party dress wows from every angle! Perfect for bachelorette weekends, themed soirees, and formal birthdays! She features a sleeveless sweetheart neckline with a padded bust, cowl draping, adjustable spaghetti straps, and side ruched seams that hug your curves along her short bodycon silhouette. The formal party dress is composed of a faux pearl embellished mesh fabric with a stretchy knit lining. Complete the look in statement block heels. Fit & FeaturesSleeveless sweetheart neckline, Padded bust, cowl draping, Adjustable spaghetti straps, Side ruched seams, bodycon silhouette, Mini-length hem, Faux pearl embellishments, mesh fabric, stretch knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Faux Pearl Mini Party Dress in White | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Day Date Outfits
Day dates are a whole mood—think sunshine, iced lattes, and the thrill of what’s-next, whether you’re heading to a cute café, hitting the farmer’s market, or just living your main character moment at a museum. Picking the right outfit isn’t just about looking good (though, let’s be real, that’s always a priority), it’s about feeling unstoppable from brunch to that spontaneous walk in the park. When it comes to day date outfits, versatility is queen. You want pieces that can handle a little adventure, a lot of compliments, and maybe even a surprise change of plans. Flowy skirts that catch the breeze, flirty dresses that twirl just right, and tops that serve effortless “I woke up like this” energy—these are the secret weapons every Windsor girl keeps on deck. And let’s not forget the accessories: a killer pair of sunnies, the perfect bag for stashing lip gloss and phone numbers, and shoes that keep up with your every move. Whether you’re shopping for yourself (because you deserve it, obviously) or hunting for a gift that’ll make your bestie’s heart skip a beat, these outfits are all about making memories and turning heads.
Gifting a day date look is like handing someone a ticket to their own rom-com montage—imagine the smile when they unwrap a dreamy dress or a top that just screams “let’s go out.” These pieces are made for the girl who’s always down for a little adventure, who turns every coffee run into a photo op, and who never says no to a spontaneous road trip. And if you’re the one curating your own closet, think about how each item will carry you through all the little moments: laughing over pastries, wandering through boutiques, or dancing in the street because your song came on. The best day date outfits are the ones that move with you, that make you feel like you could take on the world (or at least the cutest rooftop bar in town). And when the sun starts to dip and the vibe shifts from playful to a little more flirty, you’ll be glad you picked a look that’s as ready for a candlelit dinner as it was for that morning mimosa. If you’re vibing with the idea of taking your look from day to night, don’t miss our picks for Casual Date Night Outfits—because your style should be as unstoppable as you are.
Every Windsor girl knows the power of a well-chosen outfit—it’s not just about the clothes, it’s about the confidence they bring. Day date fits are your permission slip to be bold, to mix prints and textures, to play with color and show off a little (or a lot). Picture yourself in a breezy skirt that makes you want to skip down the sidewalk, or a top that’s equal parts sweet and sassy—these are the moments when your style gets to shine. And if you’re gifting, you’re not just giving fabric, you’re giving all the possibilities that come with it: the inside jokes, the new places, the stories that’ll get told again and again. So whether you’re planning the ultimate girls’ day out, celebrating a new crush, or just want to treat yourself to something that feels like a little sunshine in your closet, remember: the right outfit doesn’t just change your look, it changes your whole vibe. Here’s to making every day date unforgettable, one killer outfit at a time.