Casual Fit And Flare Dresses
Casual fit and flare dresses are your secret weapon for looking effortlessly cute while keeping it comfy. Whether you’re catching up with your crew, running errands, or just living your best life, these flirty silhouettes bring the fun without trying too hard. Get ready to twirl through every plan on your calendar—because when you slip into a fit and flare, you’re instantly that girl who knows how to turn heads and own the moment.
$68.90
An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back design.
$46.90
A white skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$20.97 $45.90 54% off
A royal blue satin skater dress with detachable rhinestone straps and a flattering fit-and-flare silhouette.
$64.90
A sage woven skater dress with a lace-up back and asymmetric drop-waist for a sweet summer look.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$44.90
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$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.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and a flirty double-layered skirt.
$49.90
A light blue satin skater dress with a floral pattern and corset bodice for a coquette vibe.
$44.90
A black floral skater dress featuring a corset bodice and bubble hem for a flattering silhouette.
$49.90
A charming white eyelet skater dress with adjustable straps and a tie-back design.
$28 $39.90 30% off
A khaki woven midi dress featuring a smocked bodice, ruffled hem, and dual spaghetti straps.
$52.90
A white floral skater dress with a corset bodice and lace-up back for a feminine touch.
$19.97 $42.90 53% off
A charming ivory skater dress with dainty floral print and faux button accents in a halter style.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$42.90
A white skater dress with tie-back halter straps and a flattering V-shaped drop waist.
$49.90 - $52.90
A black linen skater dress featuring a corset lace-up back and sweetheart neckline with bust tie.
$19.97 $59.90 67% off
A dreamy white floral skater dress featuring a corset bodice and lace-up back.
$49.90
A white woven knit mini dress featuring a sleeveless V-neckline and a flared A-line silhouette.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$19.97 $44.90 56% off
A denim skater dress featuring a corset bodice, tie-shoulder straps, and a mini-length silhouette.
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$19.97 $38.90 49% off
A black mesh fit and flare mini dress featuring sheer sleeves and a low back design.
$54.90
A chic ivory strapless skater dress with a floral pattern and tie-back bow design.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$42.90
A black skater dress with a sweetheart neckline and flattering low-cut back in woven fabric.
$24.97 $54.90 55% off
A flirty ivory skater dress with a ditsy floral print and tiered ruffled silhouette.
$49.90
An airy white eyelet skater dress featuring a lace-up bust, lace trim, and adjustable tank straps.
$59.90
An ivory cotton floral midi dress featuring puff sleeves, a V-neckline, and a flattering A-line silhouette.
$45.90
A navy blue floral chiffon skater dress featuring a V-neckline, spaghetti straps, and a ruffled hem.
$79.90
A navy blue skater dress with a glitter mesh fabric, ruched bodice, and ruffled skirt.
$52.90
A pink skater dress with puff sleeves, lace trim, and a flattering bubble hem.
$9.97 $44.90 78% off
A dark marsala skater dress with a floral pattern, lace-up back, and faux button accents.
$49.90
A light blue striped woven skater dress featuring a drop waist, pleated skirt, and mini bow detail.
$49.90
A white polka dot skater dress with a halter V-neck, tie-back bow, and textured woven fabric.
$59.90
A white floral chiffon skater dress featuring a strapless sweetheart neckline, lace trim, and padded cups.
$49.90
A natural floral cotton skater dress featuring a corset-inspired bodice, pleated trim, and voluminous hem.
$46.90
A blue floral eyelet skater dress with flutter sleeves, tiered A-line silhouette, and tie-back detail.
$42.90
An ivory floral mini dress featuring puff sleeves, a square neckline, and flattering skater silhouette.
$42.90
A light blue gingham skater dress featuring a smocked waist, sweetheart neckline, and adjustable straps.
$65.90
A navy blue eyelet mini dress featuring a strapless neckline, strappy back, and ruffled skater silhouette.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$32.90
A chic denim strapless A-line mini dress with pleated bust and stretchy knit fabric.
$36.90
An elegant off-the-shoulder natural midi dress with a stretchy knit fabric and flared hem.
$99.90
A light blue floral jacquard skater dress featuring a corset bodice, metallic threading, and hidden pockets.
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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
Casual Fit And Flare Dresses
When it comes to nailing that effortlessly cute vibe, nothing slays quite like fit and flare casual dresses. These beauties are the ultimate style chameleons—perfect for brunch with your besties, a last-minute coffee date, or that “just because” girls’ night out. The magic is all in the silhouette: a cinched waist that gives you that snatched look, paired with a skirt that twirls with every step. Whether you’re after a flirty mini or a breezy midi, fit and flare casual dresses bring a little main character energy to every moment. We’re talking about dresses that move with you, hug you in all the right places, and make you feel like you could take on the world (or at least the dance floor). Picture this: you’re running errands with your favorite playlist on blast, catching up with friends at a rooftop hang, or just living your best life—these dresses are here for it all. And let’s be real, they’re basically the MVP of your closet because they transition from chill hangs to spontaneous plans without breaking a sweat.
Shopping for fit and flare casual dresses is all about finding those little details that make you feel unstoppable. Think playful ruffles, flirty cutouts, and dreamy prints that match your mood. Comfort is key, so look for soft fabrics with a hint of stretch—because you deserve to look fab and feel comfy at the same time. These dresses are a go-to for gifting, too. Got a friend who’s always on the move or a little sis who’s leveling up her wardrobe? A fit and flare dress is the ultimate “I got you” present—fun, flattering, and guaranteed to get all the compliments. And if you’re planning a getaway or just want to bring some fresh energy to your everyday, these dresses pack like a dream and are always ready for a photo op. For those days when you want to keep things classic but still turn heads, check out our collection of Fit And Flare Black Dresses—timeless, chic, and totally iconic.
From laid-back weekends to those “just because” moments, fit and flare casual dresses are the ultimate confidence boosters. They’re made for the girl who’s always down for a little fun, who loves to spin around just because she can, and who knows that style is all about feeling good in your own skin. Whether you’re dressing up for a casual dinner, hitting up a festival, or just vibing through your day, these dresses are ready to keep up with your every move. So go ahead—embrace the twirl, soak up the good vibes, and let your fit and flare dress do the talking.