Cute Date Outfits
Ready to serve main character energy? Cute date outfits are your secret weapon for turning every moment into a rom-com montage. Whether it’s a flirty coffee run, rooftop dinner, or spontaneous adventure, these looks bring the charm and confidence you need to keep them guessing—and totally obsessed. Get ready to crush hard on your own reflection and let your style do all the flirting.
$32.90
A pink mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night out.
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and halter neck design.
$69.90
A white bodycon mini dress with iridescent rhinestones and faux pearls on sheer mesh fabric.
$68.90
An ivory floral jacquard satin skater dress with a corset bodice and lace-up back.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$35.90
A pink sleeveless bodycon midi dress with stretchy knit fabric and a flattering square neckline.
$39.90
A black knit romper featuring polka dots, a strapless neckline, and tiered ruffled overlay.
$10.97 $24.90 56% off
A black ribbed knit crop top with a lace-up back and form-hugging fit for trendy style.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$9.97 $59.90 83% off
A charming red gingham skater dress featuring an open back, ruffled hem, and lace-trimmed neckline.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$48.90
A pink mesh midi dress with a ruffled hem and a sophisticated V-wired square neckline.
$42.90
A strapless pink lace skater dress with ruffled hem, perfect for a flirty night out.
$44.90
A strapless black lace romper featuring a pleated mini hem and flattering waist accentuation.
$26.90
A taupe knit halter crop top featuring a knotted bust, tie straps, and a center split design.
$39.90
A white woven fabric corset top featuring a collared V-neckline and flexible boning.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$9.97 $39.90 75% off
A black bodycon mini dress with an asymmetrical hem, cutout bust, and sheer mesh sleeves.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$9.97 $48.90 80% off
A light blue woven A-line dress featuring a corset bodice, lace-up back, and sweetheart neckline.
$9.97 $42.90 77% off
A sultry berry knit midi dress with a strapless cowl neckline and asymmetric high slit.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini-length hem.
$22.90
A sleek black bodycon mini skort with faux leather fabric and a high-rise waist.
$39.90
A mid-rise denim mini skort with an adjustable belted waist and form-hugging silhouette.
$24.90
A flirty ivory crop top featuring a plunge halter neckline and dainty lace trim.
$32.90
A black mini bodycon dress with a sweetheart neckline and dramatic ruched bell sleeves.
$39.90
An eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline in white.
$34.90
A black crepe strapless mini dress with a chic fold-over neckline and bodycon silhouette.
$21.97 $42.90 49% off
An elegant brown ribbed knit mini dress with a scoop neckline and faux topper long sleeves.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$9.97 $49.90 80% off
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$38.90
A brown knit mini dress featuring a paisley burnout pattern, halter cowl neckline, and asymmetrical cutout.
$44.90
A chic black short dress with sheer mesh sleeves and a sleek satin A-line silhouette.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$49.90
A pink floral mesh bodycon midi dress featuring off-the-shoulder sleeves, ruching, and a sweetheart neckline.
$19.97 $39.90 50% off
A taupe striped ribbed knit mini dress featuring a strapless sweetheart neckline with knot and keyhole details.
$44.90
A black mesh-lined skater dress featuring a halter neckline, hoop insert, cutout bodice, and ruffled hem.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$19.97 $34.90 43% off
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$89.90
A playful pink A-line short dress featuring lace trim, adjustable straps, and hidden side pockets.
$52.90
A blue mesh mini dress with rhinestone embellishments, adjustable straps, and an asymmetric ruffled design.
$36.90
A black nylon mini dress featuring a fitted A-line silhouette, square neckline, and hidden shorts.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$38.90
A black mesh-lined bodycon mini dress featuring short puff sleeves, a sweetheart neckline, and side cutouts.
$54.90
An airy white chiffon mini dress featuring flutter sleeves, swiss dot pattern, lace trim, and pleated A-line silhouette.
$21 $29.90 30% off
An adorable charcoal plaid mini dress with sheer lace trims and a chic center bow detail.
Now Trending
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 Pink | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS
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: L | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in White | Size: L | Knit Fabric/Satin Fabric
Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: M | 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: M | Knit Fabric
Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White | Size: M | Knit Fabric/Rhinestone/Mesh Fabric
Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Pink | Size: L | Knit Fabric
Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/Satin Fabric
Make yourself known in this satin mini dress as you step into the club or party! The short dress is designed with a strapless neckline with non-slip grip lining, a pleated bust and side seam, a flattering bodycon silhouette, and a mini-length hem. Style the satin dress with rhinestone heels for a charming sparkle! Fit & FeaturesStrapless neckline, non-slip grip lining, Pleated bust and side seam, Bodycon silhouette, Mini-length hem, Silky satin fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Known Satin Strapless Pleat Mini Dress in Pink | Size: L | Rhinestone/Satin Fabric
Cute Date Outfits
When it comes to picking out cute date outfits, you know the drill—this is your moment to shine, to flirt with your style, and to serve up a little main character energy. Whether you’re headed out for coffee with your crush, catching a matinee, or planning a spontaneous picnic in the park, your outfit should be just as fun and fearless as you are. Think flirty skirts that twirl with every step, dreamy dresses that make you feel like you just stepped out of a rom-com, and tops that show off your personality (and maybe a little shoulder). It’s all about finding those pieces that make you feel like you’re totally owning it—because when you walk in feeling confident, the vibe is instantly elevated. These looks aren’t just for first dates, either. They’re perfect for brunch with your girls, a casual stroll with your S.O., or even a solo adventure when you want to romanticize your own life. The best part? These styles are versatile enough to take you from daytime hangs to late-night ice cream runs, with just a quick swap of accessories or a change of shoes.
Shopping for cute day date outfits isn’t just about what’s trending; it’s about what feels right for you, your plans, and your mood. Maybe you’re the type who loves a soft, flowy dress that catches the breeze and makes you want to dance down the street. Or maybe a sleek pair of jeans and a sassy crop top is more your speed—effortless but still serving looks. Don’t forget those little details that make an outfit pop, like a dainty necklace, a playful bag, or a pair of shoes that were basically made for walking (and maybe a little flirting). If you’re shopping for a gift, these pieces are a sweet way to show your bestie or sister that you’re rooting for their next big adventure—because everyone deserves to feel gorgeous and unstoppable on their big day out. The right outfit can turn a regular afternoon into a memory you’ll want to replay over and over, and trust, you’ll be reaching for these pieces again and again, whether it’s for a spontaneous coffee run or a planned day of exploring new spots around town.
And if your cute day date turns into dinner and drinks (because, hello, who doesn’t love a plot twist?), you’ll want to have an outfit that can keep up. A quick accessory swap or adding a little shimmer can take your look from “cute and casual” to “effortlessly glam” in no time. For those moments when your day date turns into a night out, check out our Dinner Date Outfits for inspo that’ll have you glowing from appetizers to after-hours. No matter where the day takes you, remember: you’re the vibe, you’re the moment, and your outfit should always be as bold, bright, and unforgettable as you are.