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.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$9.97 $49.90 80% off
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$32.90
A playful light blue cotton mini skirt featuring a pinstriped print and flouncy bubble hem.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$44.90
A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.
$46.90
A chic black halter romper with a pleated mini-length hem and form-hugging bodice.
$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 glamorous black lace bustier with rhinestones, featuring padded cups and adjustable spaghetti straps.
$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.
$19.97 $39.90 50% off
A chic white glitter lace bodycon dress with adjustable straps and an asymmetric hem.
$69.90
A white bodycon mini dress adorned with iridescent rhinestones and faux pearl embellishments.
$35.90
A sage bodycon mini dress with a pleated cowl neckline and stretchy knit fabric.
$46.90
A black strapless romper with rhinestone embellishments, offering a form-hugging silhouette and high waist.
$68.90
An ivory floral jacquard satin skater dress with a corset bodice and lace-up back.
$29.90
A black floral lace long sleeve top featuring a V-neckline, lined cups, tie-front, and ruffle details.
$69.90
A bold black mesh mini dress with studded rhinestones, ruching, and sheer long sleeves.
$24.90
A high-rise off-white knit mini skirt featuring side ruching and a ruffled hem in a bodycon fit.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$89.90
A black bodycon dress with faux pearl and beaded accents, featuring sheer sleeves and a wrap hem.
$59.90
A green satin off-the-shoulder midi dress with a sweetheart neckline and ruched wrap design.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$64.90
An elegant black mesh dress featuring an off-the-shoulder neckline, sheer long sleeves, and a high side slit.
$59.90
A navy blue velvet mermaid dress with a floral pattern, sleeveless cowl neckline, and high-side slit.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$59.90
An ivory jumpsuit with faux pearl embellishments, sweetheart neckline, and wide-leg silhouette for elegance.
$59.90
A green satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$34.90
An edgy black denim skort featuring a mid-rise fit, studded pocket trim, and bodycon mini-length style.
$19.97 $79.90 75% off
A navy blue satin dress with a plunging sweetheart neckline and pleated wrap silhouette.
$9.97 $49.90 80% off
A black velvet mini dress with a twist accent, open back, and chic side slit.
$9.97 $44.90 78% off
A black velvet mini dress with a one-shoulder neckline and wrap-around waist cutout.
$34.90
An olive green twill skort featuring a belted mid-rise waist, bodycon fit, and four-pocket styling.
$30.90
A bold red mule featuring delicate faux leather straps, a square toe, and a comfortable kitten heel.
$59.90
A black sequin mini dress with a halter neckline, waist cutouts, and an open back.
$44.90
An elegant burgundy velvet midi dress with a lace-trimmed sweetheart neckline and corset bodice.
$29.90
A black sheer lace dress featuring a sweetheart neckline and partially open back with tie straps.
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Slip into the luxe vibes of Mayra! Designed to highlight your figure, this formal satin dress delivers a chic form-hugging fit and a high slit for effortless movement. Fit & FeaturesSmooth satin-knit fabric, moderate stretch, Sleeveless square neckline, spaghetti straps, Fitted bodice, side hip pleating, Form-fitting silhouette, high-cut front slit, Floor-length hem, Style runs small, Where to Wear:Homecoming, weddings, black-tie parties, galas, military balls, engagement parties, rehearsal dinners, bridal celebrations, birthday events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Mayra Formal Satin Slit Long Dress in Sage | Size: S | Satin Fabric
Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: XS | Rhinestone
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
Chic and glamorous, the Rowena sequin mermaid long dress will stylishly elevate your formal night-out look. With a lace-up strap design and fitted mermaid silhouette with a high slit, you'll deliver stunning style. Fit & FeaturesSheer mesh fabric, knit lining, moderate stretch, embroidered sequin scroll design, Sleeveless square neckline, padded bust, Spaghetti straps, open back, lace-up strap design, tie closure, Lower back zipper with hook and eye closure, High waist seam, Fitted floor-length mermaid silhouette, high front slit, Runs true to size, Where to Wear:Prom, black-tie parties and galas, fancy engagement parties Free Shipping on All Orders Over $75. | Windsor Rowena Sequin Mermaid Dress in Navy Blue | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Lavish yourself with a luxe formal dress that elevates your special occasion outfit! Cheyenne features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit on the floor-length hem, and a curve-hugging A-line silhouette. The long dress is composed of a lined velvet fabric that offers a moderate stretch. Complete the look with rhinestone heels and a sphere clutch. Fit & FeaturesOne-shoulder neckline, wired V-neck bust, Fitted long sleeve, High side slit, floor-length hem, A-line silhouette, Lined velvet fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black-2 | Size: S | Rhinestone/Velvet Fabric
Make a sparkly statement at your next soiree in the trendy glam Addison glitter formal dress! Bring radiance to the room in this floor-length dress with a sleek design that fits like a glove. Fit & FeaturesSheer glitter mesh fabric, full knit stretchy lining, Sleeveless cowl neckline, spaghetti straps, High waist seam, Floor-length fitted silhouette, Runs true to size, Where to Wear:Prom, black tie weddings, galas, special date nights, rehearsal dinner Free Shipping on All Orders Over $75. | Windsor Addison Glitter Mesh Formal Dress in Black | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Embellished with light-catching sequins, the Bethanie formal dress is a clear stunner with a lace-up back and a flattering mermaid silhouette with a floor-length hem. Fit & FeaturesSequin-scroll pattern, mesh fabric, stretch knit lining, Sleeveless V-neckline, padded bust, Lace-up back, zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Yellow | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Black | Size: L | Stretchy Fabric/Rhinestone
Dare to stun in the Jamie satin formal dress crafted with silky satin fabric for a gorgeous sheen. The bold plunge halter neckline and open lace-up back will turn heads while the fitted column silhouette flaunts your curves. Fit & FeaturesSilky satin fabric, short knit stretchy lining, Plunge halter V-neckline, shoulder straps, padded bra cups, Lace-up open back, lower zipper with hook-eye closure, High side slit, Fitted column silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, galas, and black-tie soirees. Free Shipping on All Orders Over $75. | Windsor Jamie Lace-Up Satin Formal Column Dress in Red | Size: XS | Knit Fabric/Satin Fabric
The Rose formal long column dress is the perfect combination of elegance and glamour with a sheer corset trim and high-side slit for effortless allure! Fit & FeaturesMesh fabric, partial stretchy knit lining, Sleeveless sweetheart neckline, cowl pleating, Adjustable spaghetti straps, crisscross open back, Padded bust, sheer corset bodice, flexible boning, Side ruched seams, fitted column silhouette, High-side slit, floor-length hem, Style runs small, Where to Wear:Prom, weddings, bridesmaids, rehearsal dinners, cocktail soirees, and dressed-up date nights. Free Shipping on All Orders Over $75. | Windsor Rose Formal Mesh Corset Column Dress in Green | Size: M | Knit Fabric/Mesh Fabric
Day Date Outfits
There’s something electric about getting ready for a day date—the kind of plans that start with sunshine, spill into golden hour, and maybe even end with spontaneous adventures. Whether you’re meeting up for coffee, strolling through a downtown art walk, or heading out for an impromptu road trip, your outfit sets the vibe long before you even say hello. Day date looks are all about that effortless balance: cute enough to turn heads, but comfy enough to keep up with wherever the day takes you. Think breezy skirts that twirl with every step, flirty dresses that catch the light just right, and tops that bring out your best features while letting you move with total freedom. These aren’t just clothes—they’re your co-conspirators in making memories, designed for the girl who’s never afraid to say yes to a little adventure. When you’re choosing your look, it’s all about pieces that let your personality shine, whether that’s with a bold pop of color, a playful cut-out, or a touch of sparkle. And let’s be real: the best day date outfits are the ones that make you feel like the main character in your own rom-com, ready for anything from surprise ice cream stops to rooftop selfies.
Picking out the perfect day date outfit isn’t just about checking a box on your to-do list—it’s a whole mood. You want something that feels as fun and spontaneous as your plans, but still makes you feel totally put together. Flowy fabrics and easy silhouettes are your BFFs for all-day comfort, while details like ruching, tie fronts, or a cheeky slit add that extra bit of “look at me” energy. Don’t forget, these pieces also make killer gifts for your besties, sisters, or anyone who deserves a little confidence boost—because who doesn’t love opening a package and finding the perfect excuse to plan a day out? And if you’re shopping for yourself (as you should), think about how these outfits can pull double duty for brunches, picnics, or even those casual Fridays that turn into happy hour. The right look can take you from a sun-soaked patio to a candlelit dinner without missing a beat. For even more inspo on how to turn up the charm when the sun goes down, check out our Casual Date Night Outfits—because every Windsor girl knows the fun doesn’t stop when the daylight fades.
Day date outfits are about living in the moment and making every hour count, whether you’re out exploring or just soaking up good company. They’re for the girl who’s always down for a little mischief, who isn’t afraid to laugh too loud or dance in the street if her song comes on. When you’re shopping for these looks, think about what makes you feel unstoppable—maybe it’s a skirt that swishes just right, a top that shows off your favorite necklace, or a dress that hugs you in all the right places. Accessories can totally change the mood, too—a statement bag, layered necklaces, or a killer pair of shades can take your outfit from “cute” to “can’t-stop-staring.” And at the end of the day, the best outfit is the one that makes you feel like you can take on the world, whether you’re heading to a first date, hanging with your ride-or-die crew, or treating yourself to a solo adventure. With a closet full of day date options, you’ll always have the perfect excuse to say yes to whatever comes your way—because you deserve to look and feel amazing, every single day.