Outfits For Wine Tasting
Sipping on a velvety red or a crisp white calls for outfits that are as sophisticated and playful as the wine itself. Whether you're swirling your glass at a charming vineyard or clinking glasses at a chic wine bar, our curated collection of outfits for wine tasting is here to help you make a splash. Think breezy dresses that dance with the breeze, stylish skirts that pair perfectly with your favorite heels, and tops that bring just the right amount of flair. These looks promise to keep you effortlessly chic as you savor every note and nuance of your tastings. Cheers to making memories in style! 🍷✨
$32.90
A chic wine-colored strapless mini dress with pleated bust and flowy A-line silhouette.
$36.90
An elegant natural off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$42.90
A wine satin mini dress with rhinestone straps, ruched seams, and a form-hugging silhouette.
$54.90
A wine satin midi dress featuring a corset seam bodice and pleated faux wrap hem.
$36.90
A wine-colored knit bodycon midi dress with a surplice V-neckline and spaghetti straps.
$79.90
An elegant wine satin dress with intricate embroidery, beaded accents, and a flattering curve-hugging silhouette.
$59.90
A black crepe jumpsuit featuring a floral applique corset bodice and wide-leg pants with pockets.
$9.97 $59.90 83% off
A wine-colored velvet formal dress with an off-the-shoulder neckline and high side slit.
$19.97 $42.90 53% off
A wine-colored glitter mesh midi dress with a V-neckline, ruching, and an asymmetrical hem.
$64.90
A wine velvet mermaid dress with a ruched halter neckline and partially open back.
$52.90
A white eyelet lace skater dress featuring a scoop neckline and ruffled mini-length hem.
$76.90
A wine-colored knit mermaid dress with a one-shoulder cowl neck and ruched bodice.
$34.90
A mocha halter jumpsuit featuring a cutout bodice and flattering wide-leg silhouette in stretchy knit.
$29.97 $69.90 57% off
A wine-colored mermaid dress featuring glitter mesh, a plunging V-neckline, and a high front slit.
$46.90
A mauve satin strapless midi dress with a pleated neckline and flirty side slit.
$64.90
A wine velvet mermaid dress with a glittery corset bodice and adjustable spaghetti straps.
$42.90
A wine-colored mini dress featuring sheer mesh, crepe knit lining, and a ruched bodycon fit.
$22.97 $54.90 58% off
A wine-colored satin jumpsuit featuring a strapless cutout bodice and wide-leg silhouette.
$19.97 $42.90 53% off
A charming ivory midi dress featuring a ditsy floral print and lace-trimmed sweetheart neckline.
$54.90
A wine velvet bodycon mini dress with beaded applique cups and adjustable spaghetti straps.
$32.90
A wine-colored knit mini dress with a halter neckline and flirty cutout bodice.
$44.90
A wine-colored rib knit bodycon midi dress with a square neckline and center back slit.
$9.97 $54.90 82% off
A wine velvet mini dress with a ruched bodycon silhouette and adjustable spaghetti straps.
$9.97 $38.90 74% off
A wine velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$19.97 $34.90 43% off
A chic black bodycon midi dress with a high slit, adjustable straps, and stretchy knit fabric.
$42.90
A navy blue knit midi dress with a sleeveless cowl neckline and chic high front slit.
$54.90
A dazzling white bodysuit with rhinestone embellishments, padded cups, and a sheer mesh design.
$69.90
A wine-colored formal dress with a glitter mesh fabric, cowl neckline, and floor-length silhouette.
$32.90
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, a high slit, and a curve-hugging silhouette.
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and flattering straight-leg pants.
$38.90
A white sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$74.90
A navy blue glitter knit mermaid dress with a square neckline and lace-up open back.
$36.90
A chic pink skater dress with a ribbed knit, off-the-shoulder neckline, and long fitted sleeves.
$29.97 $54.90 45% off
A wine-colored glitter-knit mini dress with a cowl neckline and ruched bodycon silhouette.
$29.97 $54.90 45% off
A burgundy formal dress with sheer mesh sleeves, high slit, and curve-hugging silhouette.
$46.90
A brown woven midi dress with a ditsy floral print, corset bodice, and high front slit.
$89.90
An orange bodycon dress with glitter polka dots, lace-up back, and adjustable spaghetti straps.
$59.90
A sleek eggplant column dress with a cutout accent and high side slit for sultry allure.
$59.90
A wine-colored strapless formal dress with a high slit, crafted from luxurious slinky knit fabric.
$89.90
A glamorous burgundy mermaid dress with glitter knit fabric, ruching, and a stylish back cutout.
$38.90
A red knit mini dress with a pleated bust, spaghetti straps, and an A-line silhouette.
$46.90
A chic black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$139.90
An elegant wine tulle dress with rhinestone embellishments and a flattering V-neckline for formal events.
$38.90
A pink ribbed knit midi dress with a V-neckline, spaghetti straps, and a front slit.
$42.90
A black ribbed knit midi dress featuring a turtleneck, long sleeves, and a high side slit.
$35.90
A natural-colored sleeveless wrap mini dress in stretchy knit fabric with a form-hugging fit.
$69.90
A wine-colored glitter mermaid dress with a lace-up back and high front wrap slit.
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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: L | 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 Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh 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
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 Black-2 | Size: XL | Knit Fabric
Bring the dazzling glamour to the party in this long sleeve rhinestone mesh mini dress! Designed with a stretchy sheer mesh fabric with a partial knit lining, the mini-length dress is accented with all-over rhinestone embellishments for a gorgeous and chic shine. The square neckline shapes the bodice, and the unlined long sleeves have slit accents and flare out for a trendy look. The bodycon silhouette will hug your gorgeous curves. Style this mini dress with rhinestone heels for all the more sparkle. Fit & FeaturesStretchy sheer mesh fabric, partial knit lining, Rhinestone embellishments, Square neckline, Long bell sleeves with slit detail, Back zipper, hook and eye closure, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dazzling Glam Long Sleeve Rhinestone Mesh Mini Dress in Beige | Size: XL | Knit Fabric/Rhinestone/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 Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
The first step is picking the right dress. You're going to be working it in this figure-hugging mini! Put your hair in a half-up-do and slip into some heels for a bomb AF look! The dress features a sleeveless cowl neckline, spaghetti straps that cross at the back, and an asymmetrical hem. Complete the outfit with sleek hoop earrings. Fit & FeaturesSleeveless drapey cowl neckline, Spaghetti straps, cross at back, Mini length, asymmetric hemline , Smooth knit fabric, metallic sheen , Form-hugging fit , Plenty of stretch , Runs true to size, Free Shipping on All Orders Over $75. | Windsor All The Right Moves Cowl Neck Mini Dress in Green | Size: S | 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
Outfits For Wine Tasting
When it comes to wine tasting, it’s not just about what’s in your glass—it’s about the whole vibe. Picture this: you and your crew, sun-dappled vineyards stretching in every direction, laughter bubbling over the clink of glasses, and you’re feeling absolutely unstoppable in an outfit that’s as unforgettable as the day itself. That’s the magic of curating the perfect wine tasting look. Whether you’re planning a girls' getaway, celebrating a birthday, or just living your best life on a spontaneous day trip, the right outfit sets the tone for every memory made. Think light, breezy fabrics that move with you as you wander between cellars, playful cuts that flirt with the breeze, and details that pop against a backdrop of rolling grapevines. These are the pieces that keep you cool under the sun, comfy for hours of exploring, and camera-ready for those impromptu group pics that always end up as your new favorite profile photo.
Shopping for wine tasting outfits is all about balancing style and practicality with a dash of main character energy. You want looks that feel elevated but never fussy—outfits that say “I’m here to sip, swirl, and slay.” Think easy-to-layer pieces for those temperature swings between sun-soaked patios and cozy wine cellars, or a playful midi skirt that lets you twirl your way from one tasting to the next. Accessories become your secret weapon: a statement hat for a little drama, a crossbody bag to keep your hands free for all those tasting notes (and maybe a charcuterie board or two). And if you’re shopping for someone special, these picks make the kind of gifts that turn simple plans into standout experiences—think bestie birthdays, bachelorette surprises, or a “just because” treat for your favorite wine-loving partner-in-crime. Every piece is chosen with the Windsor girl in mind: bold enough to make an entrance, effortless enough to keep the good vibes going all day long, and versatile enough to transition from vineyard hangs to that cute dinner reservation you booked for later. If you want to keep the energy going after your last pour, check out our Fancy Dinner Outfits for a seamless switch from daytime sipping to a night out that’s all sparkle and sophistication.
Let’s be real—wine tasting isn’t just an event, it’s an aesthetic. It’s the kind of day where you want to feel a little extra, a little adventurous, and a lot like the main character in your own rom-com. You’re there for the memories, the inside jokes, and the endless photo ops with your favorite people. That’s why the right outfit is more than just clothes—it’s your ticket to confidence, comfort, and a whole lot of compliments. Imagine the perfect dress that lets you lounge on a picnic blanket or dance between the vines, or a chic set that looks just as good perched on a tasting room stool as it does strolling through a sunlit field. With the right picks, you’ll be ready for every toast, every laugh, and every “OMG, where did you get that?” moment. So go ahead—make your wine tasting adventure one for the books, with looks that are as bold and fearless as you are.