Fall Date Outfits
Sweater weather is here, and so are those dreamy fall date outfits that will have you feeling like the main character in your own rom-com! Whether you're strolling through a pumpkin patch, sipping on a spiced latte, or cozying up by a crackling fire, it's all about embracing those rich hues and snuggly layers. Picture yourself wrapped in the perfect blend of chic and comfy, ready to make unforgettable memories. From flirty skirts that swish with every step to tops that bring out your inner glow, these looks are all about capturing the essence of autumn romance. Let's make this season the one where you turn heads and steal hearts effortlessly. 🍂💖
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and halter neck design.
$84.90
A light blue strapless bodycon mini dress with beaded mesh fabric and elegant cowl neckline.
$49.90
A black faux leather and mesh jacket with illusion stripes, perfect for layering over chic outfits.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$9.97 $42.90 77% off
A grey glitter knit mini dress with a one-shoulder neckline and ruched side seams.
$34.90
A chic blue satin mini dress featuring a strapless pleated neckline and flattering A-line silhouette.
$59.90
A charming red gingham skater dress featuring an open back, ruffled hem, and lace-trimmed neckline.
$9.97 $39.90 75% off
A black bodycon mini dress with an asymmetrical hem, cutout bust, and sheer mesh sleeves.
$19.97 $34.90 43% off
An off-white abstract mini dress featuring a one-shoulder neckline and a 70s-inspired sheer sleeve.
$69.90
A black flocked floral velvet skater dress with a sweetheart neckline and flirty spaghetti tie straps.
$42.90
A black velvet mini dress with an asymmetric one-shoulder neckline and ruched bodycon silhouette.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$36.90
A sultry brown knit midi dress featuring a lace-up back, ruched bodycon fit, and side slit.
$38.90
A burgundy knit skater dress featuring a cold-shoulder design and corset-style seams for a sleek look.
$19.97 $44.90 56% off
A strapless black knit mini dress featuring a drop waist and tiered ruffled asymmetric hem for flirty style.
$9.97 $54.90 82% off
A wine velvet mini dress with a ruched bodycon silhouette and adjustable spaghetti straps.
$42.90
A black skater dress with a sweetheart neckline and flattering low-cut back in woven fabric.
$21 $29.90 30% off
An adorable charcoal plaid mini dress with sheer lace trims and a chic center bow detail.
$9.97 $38.90 74% off
A wine-colored velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$54.90
An oversized black faux leather blazer with a lapel collar and chic single button closure.
$69.90
A black floor-length formal dress with a glitter mesh overlay and a cowl neckline.
$39.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$39.90
A sultry black formal dress with rhinestone straps, cowl neckline, and a high slit.
$32.90
A sultry red mesh mini dress with a cowl neckline and adjustable spaghetti straps for chic nights.
$59.90
A black glitter knit formal dress with a cowl neck, cross back, and high front slit.
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$74.90
A navy blue glitter knit mermaid dress with a square neckline and lace-up open back.
$69.90
A white bodycon mini dress with iridescent rhinestones and faux pearl embellishments on sheer mesh.
$89.90
A dazzling periwinkle skater dress with sequin embellishments and a lace-up open back.
$9.97 $54.90 82% off
A brown glitter-knit mini dress with a cowl neckline and bodycon silhouette, perfect for formal events.
$29.90
A pink oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem for cozy style.
$19.97 $54.90 64% off
A burgundy formal dress with sheer mesh sleeves, high slit, and curve-hugging silhouette.
$9.97 $42.90 77% off
A glittery black mini dress with a one-shoulder balloon sleeve and front tie ruching.
$59.90
A sage glitter knit formal dress with a sleeveless cowl neckline and thigh-high side slit.
$19.90
A chic black sheer mesh bolero with blouson sleeves, perfect for layering over any outfit.
$28.90
A trendy brown off-the-shoulder top with smooth knit fabric and flattering ruched side seams.
$89.90
A sage mermaid dress with a glittery knit, lace-up back, and high side slit for elegance.
$26.90
An ivory faux fur shawl with a satin-like lining and optional hook-eye closure.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$42.90
A stylish pair of brown high-rise cargo pants with adjustable drawcord hems and multiple pockets.
$69.90
An elegant white bodycon dress featuring a low back and ruffled bubble hem for chic occasions.
$26.90
A flirty ivory midi skirt with ruched detailing and an asymmetric high-side slit in stretchy knit.
$44.90
A charming ivory pointelle knit skater mini dress with a scoop neckline and wide shoulder straps.
$39.90
A pink glitter knit skater dress with a strapless neckline and tiered ruffled hem.
$28.90
A sleek black nubuck stiletto heel with a square toe and adjustable ankle strap.
$29.90
A black pleated ponte skort featuring a high-rise waist and mini-length for a preppy look.
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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 Navy Blue | Size: L | 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
Fall Date Outfits
When it comes to crafting the perfect vibe for a date night, it’s all about striking that magical balance between looking like you totally planned your look, but also like you just threw it on and happened to look this good. The best date outfits are the ones that let your confidence do the talking—whether you’re headed to a candlelit dinner, a rooftop happy hour, or a spontaneous drive with the windows down and your favorite playlist blasting. You want pieces that move with you, fabrics that feel as good as they look, and silhouettes that let you show off your personality without saying a word. Think soft knits that hug you just right, faux leather that adds a little edge, and flirty details like lace, ruching, or a daring slit that says, “Yeah, I know I look amazing.” These are the outfits you reach for when you want to make a memory, not just an impression. They’re for the moments when you’re laughing so hard your mascara almost runs, when you’re sharing fries at midnight, and when you’re twirling under string lights just because you feel like it.
Shopping for date night looks is basically an act of self-love, but let’s be real, it can also be a total game changer for gifting. If you’re on the hunt for something special for your bestie, your sister, or anyone who’s got a calendar full of plans, a killer outfit is the kind of present that makes you the MVP of any group chat. These picks are perfect for anyone who loves to play with their style, mix up their closet staples, or just wants to feel like the main character for a night. And because versatility is the name of the game, you’ll find that the right pieces can take you from a cozy coffee date to a late-night adventure with just a quick swap of shoes or a swipe of lipstick. Whether you’re shopping for yourself or someone you love, focus on pieces that make you feel unstoppable—think bold colors, unexpected textures, and those little details that make you want to snap a mirror selfie before you head out the door. And if your idea of a perfect date is more about catching your favorite band live than sipping cocktails, don’t miss the inspo over on our Fall Concert Outfits page for even more ways to turn every outing into a main event.
Every Windsor girl knows that the right outfit isn’t just about what you wear—it’s about how you wear it. It’s the confidence boost before you leave the house, the way you light up when you catch your reflection, and the stories you’ll tell about that night for years to come. Whether you’re dressing for a first date or your hundredth, these looks are designed to help you feel your boldest, brightest self. Picture yourself stepping out, hair done, playlist queued, and that feeling in your stomach that says tonight could be unforgettable. That’s what these outfits are all about: amplifying your energy, hyping you up, and making sure you’re ready for whatever the night throws your way. So go ahead—choose the look that makes you feel like the best version of yourself, and let the good times roll.