Flowy Fit And Flare Dresses
Flirty, fearless, and totally twirl-worthy—flowy fit and flare dresses are your secret weapon for making an entrance (and a few heads turn). Whether you’re vibing with your squad or dancing the night away, these dresses bring the drama and the fun. Slip into a silhouette that moves with you and watch your confidence hit new highs—because every Windsor girl deserves to feel like the main character. Ready to serve looks? Flowy fit and flare dresses have you covered, bestie.
$9.97 $45.90 78% off
A royal blue satin skater dress with detachable rhinestone straps and a flattering fit-and-flare silhouette.
$36.90
A sage satin skater dress with a halter V-neckline and charming open tie-back design.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$44.90
A breezy white chiffon skater dress featuring cold-shoulder straps, a sweetheart neckline, and ruched bodice.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$49.90
A light blue satin skater dress featuring a floral brocade pattern, corset bodice, and ruffled neckline.
$49.90
A chic yellow skater dress featuring a lace-up corset bodice and adjustable tank straps.
$19.97 $44.90 56% off
A black floral skater dress with a corset bodice and bubble hem for a flattering silhouette.
$23.97 $52.90 55% off
An elegant black chiffon floral midi dress with a sweetheart neckline and adjustable straps.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$54.90
A black glitter mesh skater dress with a corset bodice and lace-up back for a custom fit.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$9.97 $59.90 83% off
A dreamy white floral skater dress featuring a corset bodice and lace-up back.
$65.90
A strapless floral skater dress featuring a bustier bodice, sweetheart neckline, and hidden side pockets.
$44.90
A flowy green gauze midi dress featuring a strapless smocked bodice and tiered A-line silhouette.
$49.90
An ivory floral skater dress featuring a corset bodice, lace-up back, and tie shoulder straps.
$79.90
A navy blue glitter mesh skater dress with a ruched bodice and cascading ruffled skirt.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$45.90
A navy blue floral chiffon skater dress featuring a V-neckline, spaghetti straps, and a ruffled hem.
$54.90
An ivory floral chiffon skater dress featuring sheer peasant sleeves, a sweetheart neckline, and button accents.
$32.90
An ivory strapless A-line mini dress with pleated bust, crafted from stretchy knit fabric.
$32.90
A mauve satin mini dress with an off-the-shoulder neckline and flattering A-line silhouette.
$26.97 $59.90 55% off
A natural floral chiffon skater dress with a strapless sweetheart neckline, lace trim, and bow.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$54.90
A black glitter skater dress with chiffon sleeves and a sweetheart neckline for dazzling occasions.
$44.90
A yellow floral skater dress with a strappy tie-back and ruffled mini-length hem.
$44.90
A charming ivory pointelle knit skater mini dress with a scoop neckline and wide shoulder straps.
$139.90
A pink floral tulle A-line gown with a strapless pleated neckline and sheer corset bodice.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$139.90
A light blue floral mesh dress with a sheer corset bodice and ruffled A-line silhouette.
$38.90
An ivory lace mini dress featuring flutter sleeves and a flattering A-line silhouette.
$69.90
A blue floral mesh skater dress with a sweetheart neckline and tiered ruffled skirt.
$44.90
A floral chiffon skater dress in ivory with a strapless smocked bodice and ruffled silhouette.
$25.97 $56.90 54% off
A floral chiffon maxi dress with a flattering A-line silhouette and flowy hem in white.
$42.90
A light blue woven midi dress featuring dainty florals, adjustable straps, and a front slit.
$42.90
An olive green gauze skater dress featuring a V-neckline, ruffled hem, and open cross-back design.
$52.90
A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.
$9.97 $38.90 74% off
A chic black mini dress with sheer flare sleeves and a daring low back design.
$52.90
A white floral A-line midi dress featuring puff short sleeves, a square neckline, and a flirty front slit.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$49.90
A playful denim halter skater dress featuring a bust cutout, drop waist, and pleated short silhouette.
$49.90
A natural chiffon mini dress featuring a dainty floral print, smocked bodice, and tiered ruffled skirt.
$59.90
A chic yellow satin skater dress with a lace-up corset bodice and lace trim neckline.
$22.97 $49.90 54% off
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$44.90
A natural gauze mini dress featuring a halter neckline, keyhole cutout, and flirty ruffled hem.
$44.90
An ethereal ivory chiffon skater dress featuring flirty ruffles and a strappy tie-back design.
$34.90
A plum floral knit midi dress featuring a strapless neckline and stylish front 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: L | 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: S | 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 Black | Size: S | Satin Fabric
Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$9.97 $45.90
78% 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: XS | 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
Short and sweet, this adorable floral skater dress will perfect your spring vibe. The lace-up corset bodice and V-shaped drop waist snatches your waist, while the flared A-line silhouette gives that flirty flair. Fit & FeaturesSmooth woven fabric with woven lining, sheer lace trims, no stretch, Sleeveless sweetheart neckline, underwire, ruched bust, tie-front detail, Thin adjustable shoulder straps, Corset bodice, structured boning, pleating, lace-up back, hidden zipper with hook-eye closure, V-shaped drop waist, Short skater silhouette, floral print, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Babe Corset Drop Waist Floral Skater Dress in Ivory | Size: XL | Sheer Lace Fabric/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 Sage | Size: XS | 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
Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural
$26.97 $59.90
55% off
Flirty and adorable, this floral skater dress makes the sweetest impression at showers or birthdays! Featuring a sweetheart neckline with delicate lace trim and a charming bow, this dress is sure to turn heads. The padded bra cups provide a perfect fit, while the skater silhouette and mini-length hem add a touch of playfulness. Complete the look with earrings and strappy heels. Fit & FeaturesFloral print, chiffon fabric lined with woven, Strapless sweetheart neckline, Lace trim and bow, Padded bra cups, Back zipper and hook-eye closure, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural | Size: M | Chiffon
Flowy Fit And Flare Dresses
When it comes to flowy fit and flare dresses, there’s just something about the way they move with you—every twirl, every step, every little shimmy on the dance floor. These dresses are the definition of effortless, with a silhouette that hugs where you want it to (hello, waist!) and flows out into a skirt that’s made for living your best life. Whether you’re headed out for a rooftop brunch with your girls or RSVPing “yes” to a last-minute invite, the fit and flare style has your back, making you feel like the main character in every room you walk into. The beauty of this look? It’s universally flattering. Seriously, it’s the dress your bestie borrows and never wants to give back, the one your sister asks to “just try on”—and suddenly you’re both fighting over who gets to wear it next. And if you’re eyeing the perfect gift for someone who loves a little drama with their style (but not the kind that ruins brunch), a flowy fit and flare dress is a total slam dunk. It’s the kind of present that says, “I see you, I know your vibe, and I want you to feel as fabulous as you look.”
Styling a flowy fit and flare dress is like having a blank canvas with endless possibilities. Dress it up with strappy heels and a sparkly clutch for a night out, or keep it chill with sneakers and a denim jacket for that spontaneous road trip. The magic is in the movement—catching the breeze as you walk, feeling the fabric swish around your legs, and knowing you look good from every angle. These dresses are made for those moments when you want to feel light, free, and just a little bit extra. And let’s be real: they’re also a lifesaver for those “nothing to wear” days. The fit and flare shape works for every body, every mood, and every plan you make (even if it’s just a solo picnic in the park with your favorite playlist on repeat). It’s the ultimate go-to for bridesmaids, grads, birthday queens, or anyone who wants to make an entrance without breaking a sweat. If you’re all about that floaty, ethereal vibe, you’ll want to check out our Chiffon Fit And Flare Dresses for even more inspo—think dreamy fabrics that turn every day into a photo op.
Here’s the secret: a flowy fit and flare dress isn’t just an outfit—it’s an instant mood boost. It’s for the girl who wants to feel unstoppable, whether she’s taking over the city or just vibing with her crew. The forgiving cut means you can actually breathe (and eat dessert), and the swirling skirt makes every spin feel like a celebration. If you’re gifting, it’s the kind of piece that makes someone feel seen, hyped up, and ready for whatever comes next. And if you’re shopping for yourself? You already know you deserve it. Just add your favorite accessories, a swipe of gloss, and you’re out the door—no stress, all confidence. Because around here, we believe every day deserves a little main character energy, and your flowy fit and flare dress is the ticket.