Flare Dresses
Calling all fashionistas ready to twirl into the spotlight—flare dresses are your ticket to a whirlwind of style and sass! These fabulous frocks are perfect for showing off your playful side, whether you're hitting the dance floor or just strutting down the street. With their flirty silhouettes and flowy vibes, flare dresses are here to make sure you own every room you walk into. So, slip into one of these beauties and let your confidence soar as you embrace the ultimate blend of chic and carefree. Let's get ready to slay, Windsor girl!
$36.90
An elegant natural off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$49.97 $99.90 50% off
A glamorous fuchsia A-line dress with rhinestones, lace-up back, and floor-sweeping hem.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$36.90
A sage satin skater dress with a V-neckline, halter strap, and flirty fit-and-flare silhouette.
$48.90
A white eyelet knit mini skater dress featuring a flirty tie-back and tiered ruffled hem.
$54.90
A black glitter skater dress with chiffon sleeves and a fit-and-flare silhouette for parties.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$49.90
A chic yellow skater dress featuring a lace-up corset bodice and adjustable tank straps.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and a flirty double-layered skirt.
$44.90
A chic black short dress with sheer mesh sleeves and a sleek satin A-line silhouette.
$54.90
A black glitter mesh skater dress with a corset bodice and lace-up back for a custom fit.
$19.97 $38.90 49% off
A chic black mini dress with sheer flare sleeves and a daring low back design.
$24.97 $54.90 55% off
A charming ivory skater dress featuring a ditsy floral print and tiered ruffled silhouette.
$79.90
A navy blue skater dress with a glitter mesh fabric, ruched bodice, and ruffled tiered skirt.
$35.90
A strapless black floral midi dress with a sweetheart neckline and trendy flare hem.
$54.90
A sage chiffon skater dress with puff sleeves, sweetheart neckline, and flirty tie-back design.
$119.90
An elegant denim tulle gown with glitter sequins, strappy back, and a flattering A-line silhouette.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$49.90
A light blue satin skater dress with a floral pattern and corset bodice for a coquette vibe.
$69.90
A blue floral mesh skater dress with a sweetheart neckline and tiered ruffled skirt.
$44.90
A black floral skater dress with a corset bodice and bubble hem for a flattering silhouette.
$44.90
A taupe paisley skater dress with a halter V-neck and stretchy smocked bodice.
$19.97 $34.90 43% off
A charcoal skater dress with a ribbed knit top and tiered ruffled chiffon A-line silhouette.
$39.97 $179.90 78% off
A glamorous orange strapless dress with floral sequin embellishments and a chic high front slit.
$52.90
A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.
$49.90
A floral ivory mini dress with a corset bodice, lace-up back, and adjustable spaghetti straps.
$42.90
A sultry red halter midi dress with a V-neckline, open back, and side slit.
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Have a twirl-worthy moment in this gorgeous and glam satin skater dress. It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back and lace-up back design, a fitted bodice with a high waist, and a flirty skater silhouette. Style this dress with rhinestone earrings and new heels. Fit & FeaturesSleeveless, square neck, adjustable spaghetti straps, Built-in padded bust, Lace-up back design, Fitted bodice, high waist seam, Skater pleated silhouette, Satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor A Moment In Satin Skater Dress in Blue | Size: L | Rhinestone/Satin Fabric
Lustrous silk for your fancy needs. Show up to the celebration in this satin skater dress designed to fit and flatter every figure in a sleeveless cowl neckline, spaghetti straps, and a form-fitting bodice that leads to a short-length hem. Complete the look in fab block heels. Fit & FeaturesSleeveless cowl neckline, spaghetti straps, Form-fitting bodice, Skater style skirt, Short-length hem, Silky smooth satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Silky Chic Satin Skater Dress in Blue | Size: M | Satin Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Pink | Size: XS | Knit Fabric
Flirt up the room at your next dressy affair in this adorable skater dress designed with a floral jacquard satin fabric for a chic look. It features a sleeveless sweetheart neckline with ruching at the bust and a tie-front detail, a corset bodice with vertical seam detailing, a lace-up back design to create that snatched fit, a V-shaped drop waist, and a short skater skirt with an iconic fit-and-flare silhouette. Fit & FeaturesFloral jacquard satin fabric with lace-trim lining, Sweetheart neckline, ruched underwire bust, tie-front detail, Thin adjustable shoulder straps, lace-up back, Corset bodice with vertical seam detailing, flexible boning, V-shaped drop waist, Short skater skirt, fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt It Up Floral Jacquard Satin Corset Skater Dress in Ivory | Size: S | Satin Fabric
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag. Fit & FeaturesSleeveless V-neckline, Halter tie-back straps, open back, Stretchy smocked high waist, Short skater skirt, tiered ruffled design, Fit and flare silhouette, Twill fabric, woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunset Happy Hour Ruffled Skater Dress in Yellow | Size: M
Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$20.97 $45.90
54% off
Show off a hint of bling in this satin skater dress for your next dressy soiree! Adorned with detachable rhinestone-embellished straps for a stunning sparkle, this dress will be the night's hit. The smooth satin-knit fabric offers plenty of stretch for comfortable wear. The short dress features a sleeveless square neckline, ruched side seams at the bodice, and a flattering fit-and-flare skater silhouette. Complete your look with rhinestone bow heels. Fit & FeaturesStretchy smooth satin-knit fabric, knit lining at the bust, Sleeveless square neckline, Detachable rhinestone-embellished thin straps, Side ruched seams at the bodice, High waist seam, Fit-and-flare skater silhouette, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue | Size: L | Knit Fabric/Rhinestone/Satin Fabric
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace. Fit & FeaturesWoven fabric with lace trim woven lining, Sweetheart neckline, ruched bust, adjustable tie-front, Tank straps, lace-up back design, Back zipper and hook-eye closure, Asymmetric drop-waist, pleated side panels, Tiered A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Darling Woven Drop-Waist Skater Dress in White | Size: XS | Woven Fabric
Be your own adorable muse in this sleeveless skater dress boasting a V-neckline and a ruffled skater silhouette. Complete the look with heels. Fit & FeaturesSheer lace fabric with knit lining, plenty of stretch, V-neckline with twist-front bust design, Adjustable spaghetti straps, V-shaped drop waist, Mini-length tiered ruffled skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Adorable Muse Ruffled Lace Skater Dress in White | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: S | Knit Fabric
Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone! Fit & FeaturesWoven fabric with woven lining, Square neckline with bust tie, Spaghetti straps, Strappy tie-back design, Skater silhouette, Ruffled mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Spring Forward Strappy Back Skater Dress in Yellow | Size: L | Woven Fabric
Flare Dresses
Let’s be real: nothing says “main character energy” quite like slipping into a flare dress and letting the world become your runway. Flare dresses are the ultimate mood-lifters—twirl-worthy, confidence-boosting, and straight-up iconic for every occasion on your calendar. Whether you’re vibing with a classic A-line silhouette, swooning over a dramatic high-low hem, or living your best life in a flared mini that flirts with every step, these styles are here to help you serve looks and collect compliments. Dresses with flare have that magical way of making you feel like the party started the moment you walked in, and honestly, who doesn’t want that kind of entrance? They’re the go-to for any girl who wants to look put-together without trying too hard—think brunches, rooftop hangs, picnics, or just because you felt cute and wanted to give your jeans a day off. Flared dresses are also a total gifting win, especially for birthdays, graduations, or “just because” moments when your bestie deserves to feel like the queen she is. The fit is forgiving, the vibe is always fun, and the twirl factor? Off the charts.
When it comes to picking out the perfect flair dress, it’s all about finding the details that match your energy. Love a little drama? Go for bold prints, statement sleeves, or a cinched waist that shows off your shape and brings extra movement. If you’re more about those subtle, effortlessly chic moments, opt for soft fabrics, delicate ruffles, or a classic flare that skims your curves just right. The beauty of flare dresses is in their versatility—you can dress them up with strappy heels and sparkling accessories for a night out, or keep it chill with sneakers and a denim jacket for that “cool girl at the coffee shop” vibe. And don’t even get us started on how perfect they are for dancing—whether you’re at a wedding, a festival, or just in your living room with your favorite playlist, a flared dress brings all the fun and none of the fuss. Pro tip: if you’re shopping for a special event, like prom or a formal, check out our stunning collection of Flare Prom Dresses to find a look that guarantees you’ll be remembered long after the last song.
Let’s not forget, flare dresses are basically made for making memories. Picture this: golden hour, your favorite people, and you in a dress that moves with you—whether you’re spinning under string lights or just catching up on the patio. These dresses are designed for the girl who loves a little extra, who isn’t afraid to stand out, and who knows that sometimes the best moments are the ones you dress up for, even if you don’t have a reason. And if you’re shopping for someone else, you can’t go wrong—flare dresses are universally flattering, easy to style, and always in style. They’re the piece she’ll reach for time and again, from late-night adventures to last-minute invites. So go ahead, pick your favorite, and let your dress do the talking. Because with a flare dress, every day is a good day to be unforgettable.