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.
$64.90
A sage woven skater dress with a lace-up back and asymmetric drop-waist for a sweet summer look.
$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.
$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.
$64.90
A natural cotton floral midi dress featuring a structured corset bodice, sweetheart neckline, and voluminous A-line skirt.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$49.90
A navy blue cotton 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.
$49.90
A charming denim skater dress featuring a halter neckline, pleated hem, and convenient side pockets.
$49.90
A light blue satin skater dress with a floral pattern and corset bodice for a coquette vibe.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, ruffled hem, and dual spaghetti straps.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$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.
$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.
$49.90 - $52.90
A black linen skater dress featuring a corset lace-up back and sweetheart neckline with bust tie.
$59.90
An ivory cotton floral midi dress featuring puff sleeves, a V-neckline, and a flattering A-line silhouette.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$79.90
A navy blue skater dress with a glitter mesh fabric, ruched bodice, and ruffled tiered skirt.
$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 black skater dress with a sweetheart neckline and flattering low-cut back in woven fabric.
$52.90
A pink skater dress with puff sleeves, lace trim, and a flattering bubble hem.
$49.90
An airy white eyelet skater dress featuring a lace-up bust, lace trim, and adjustable tank straps.
$45.90
A navy blue floral chiffon skater dress featuring a V-neckline, spaghetti straps, and a ruffled hem.
$49.90
A white polka dot skater dress with a halter V-neck, tie-back bow, and textured woven fabric.
$32.90
A chic denim strapless A-line mini dress with pleated bust and stretchy knit fabric.
$36.90
An elegant black off-the-shoulder 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.
$26.97 $59.90 55% off
A natural floral chiffon skater dress with a strapless sweetheart neckline, lace trim, and bow.
$54.90
A black glitter skater dress with chiffon sleeves and a sweetheart neckline for dazzling occasions.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$44.90
A charming ivory pointelle knit skater mini dress with a scoop neckline and wide shoulder straps.
$36.90
A black ribbed knit halter mini dress with a skater silhouette, perfect for festivals or casual outings.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$64.90
An elegant black velvet skater dress with an off-the-shoulder neckline and drop-waist design.
$38.90
An ivory lace mini dress featuring flutter sleeves and a flattering A-line silhouette.
$46.90
An adorable white eyelet mini dress with a flirty tie-back and ruffled A-line silhouette.
$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.
$42.90
An olive green gauze skater dress featuring a V-neckline, ruffled hem, and open cross-back design.
$59.90
A white floral eyelet midi dress featuring a ruffled A-line silhouette and whimsical tie-back design.
$52.90
A chic black skater dress featuring a sheer lace corset bodice and lined mesh skirt.
$46.90
A black floral halter midi dress with a flowy A-line silhouette and tie-back design.
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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
Casual Fit And Flare Dresses
When it comes to nailing that effortlessly cute vibe, nothing beats the magic of a casual fit and flare dress. This is the dress you reach for when you want to look put-together but still feel like you could twirl your way through brunch, a coffee run, or even a spontaneous road trip with your girls. The flirty silhouette—fitted at the waist, with a skirt that flares out just enough—creates a look that’s universally flattering and endlessly versatile. It’s the kind of dress that lets you move, groove, and live your best life without a second thought. Picture yourself strolling through a weekend farmer’s market, iced latte in hand, feeling the sun on your skin and the breeze catching the hem of your dress. Or maybe you’re heading to a backyard hangout, layering your casual flare dress with a denim jacket and sneakers for that “I woke up like this” energy. Whether you’re the queen of last-minute plans or the friend who always has a backup outfit in her tote, this style is your ticket to staying comfy and confident all day long.
Shopping for a casual fit and flare dress is all about finding that sweet spot between fun and functional. Think soft, breathable fabrics that keep you cool when things heat up, or playful prints and colors that match your mood. You can dress it up with a cute pair of wedges and statement earrings, or keep things low-key with your go-to sandals and a floppy hat. This is also one of those rare pieces that works for almost anyone on your gift list—your bestie who just landed her dream job, your sister who loves a little flair, or even your mom who’s always on the hunt for something easy yet chic. And let’s be real: a casual fit and flare dress is the ultimate confidence booster, giving you that extra pep in your step whether you’re heading to class, a date, or just running errands. The best part? It’s the kind of dress that makes you feel like the main character in your own movie, ready for whatever adventure comes next.
If you’re in the mood to level up your wardrobe game, don’t forget that the fit and flare silhouette isn’t just for daytime hangs. For those moments when you want to turn heads under the city lights or dance until the DJ calls last song, check out our Party Fit And Flare Dresses for even more ways to serve unforgettable looks. But for every other moment—the coffee dates, the study sessions, the spontaneous ice cream runs—a casual flare dress is your ride-or-die. It’s the dress that keeps up with your every move, gasses you up with every spin, and reminds you that style should always feel this easy.