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.

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Windsor Flirt It Up Floral Jacquard Satin Corset Skater Dress in Ivory

$68.90

An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back design.

Countless Shine Glitter Skater Dress in Lavender

$49.90

A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.

Leah Glitter Mesh Corset Skater Dress in Black

$54.90

A black glitter mesh skater dress with a corset bodice and lace-up back for a custom fit.

Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown

$46.90

A brown woven midi dress with a ditsy floral print, corset bodice, and high front slit.

Windsor Adorable Muse Ruffled Lace Skater Dress in Black

$49.90

A sleeveless black skater dress featuring sheer lace, a V-neckline, and adjustable spaghetti straps.

Floral Charm Ruffled Chiffon Tube Skater Dress in White

$44.90

A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.

Bright Side Puff Sleeve Skater Bubble Hem Dress in Pink

$52.90

A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.

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Senorita Mesh Strappy Mini Dress in Pink

$32.90

(92)

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: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Sage

$32.90

(86)

This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Sage | Size: L | Knit Fabric/Satin Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(72)

The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS

Windsor Cute Attitude Ponte Slit Mini Skort in Black

$27.90

(69)

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: L | Knit Fabric

Lena Strapless Bodycon Beaded Mesh Mini Dress in White

$84.90

(62)

Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(54)

Minimal, but never boring. This sleek mini skirt brings the heat with a flirty slit and body-hugging fit made for going out or dressing up your everyday looks. Fit & FeaturesStretchy and smooth knit fabric, High-rise elasticized waistband, Mini-length hem, short front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric

Flawless Allure Cowl Neck Bodycon Mini Dress in Light Blue

$35.90

(48)

Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Light Blue | Size: L | Knit Fabric

Stunning Sophistication Rhinestone Mini Dress in Wine

$42.90

(38)

Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/Satin Fabric

Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold

$39.90

(30)

You'll have that perfect glow in this satin mini dress at the party! This stunning mini-length dress features a strapless neckline for a classic style, and a side pleated seam adds a touch of sophistication and creates a flattering A-line silhouette. Complete the look with stiletto heels. Fit & FeaturesSatin fabric lined with stretchy knit, Strapless neckline, Side pleated seam, A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold | Size: L | Satin Fabric

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Windsor Make It Known Satin Strapless Pleat Mini Dress in Denim

$7.97 $37.90
79% off

(28)

Make yourself known in this satin mini dress as you step into the club or party! The short dress is designed with a strapless neckline with non-slip grip lining, a pleated bust and side seam, a flattering bodycon silhouette, and a mini-length hem. Style the satin dress with rhinestone heels for a charming sparkle! Fit & FeaturesStrapless neckline, non-slip grip lining, Pleated bust and side seam, Bodycon silhouette, Mini-length hem, Silky satin fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Known Satin Strapless Pleat Mini Dress in Denim | Size: L | Rhinestone/Satin Fabric

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.

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