Night Out
Plans after dark call for outfits that know how to show up. This edit of going out outfits is built for rooftop bars, concerts, birthday celebrations, and spontaneous nights that start with one drink and end somewhere unexpected. Expect curve-hugging mini dresses, statement separates, and matching sets designed to mix, match, and move with you. Cowl necklines, strapless tops, and halter silhouettes bring just the right amount of edge, while sparkly crop tops and bustiers pair effortlessly with faux leather minis or relaxed cargo pants. Finish the look with a sleek moto jacket or bomber — because a good night out always deserves a great outfit.
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Going-Out Outfits for Every Fall & Winter Plan
Windsor’s Going-Out Outfits make getting ready feel effortless, whether the plan is dinner and drinks, a bar night with friends, a date, party, or night at the club. Find curve-hugging minis, statement separates, matching sets, denim, and sexy outfits with bold details that instantly turn up your look. From laid-back nights to full-glam entrances, these night-out outfits make it easy to dress for the vibe while creating a look that feels completely your own.
What Should I Wear for a Night Out?
Start with the mood and where you're headed. For dinner or date night, try a cowl-neck or halter top with embellished jeans or a denim skort for an elevated look that doesn't feel overdone. When drinks turn into dancing, strapless tops, plunging necklines, hardware details, and open-back silhouettes bring more after-dark energy. Explore going-out tops designed to mix, match, and move with you from the first stop to the last.
For an instant outfit, going-out dresses take the guesswork out of getting ready. Bodycon minis, curve-hugging silhouettes, bold prints, and romper dresses with flirty ruffle skirts give you one-and-done options that still make a statement.
Want the whole look with even less styling? Matching sets make getting ready easy, from sparkling coordinates that bring instant party energy to trending denim sets with vests for more laid-back plans. Wear the pieces together for effortless impact, then remix them with other going-out favorites. Discover more matching sets for going-out plans when you want an instantly coordinated look.
What Going-Out Outfits Are Trending in Fall 2026?
Fall going-out style mixes seasonal color and statement denim with silhouettes that still show some skin. Try embellished jeans with a backless top for drinks, a trending denim set for a harvest event, or an asymmetrical mini with boots for a night downtown. Jorts, boleros, bold prints, and unexpected separates also give you more ways to experiment with your look, especially when Halloween plans call for an outfit that can become part of a costume or make a statement all on its own.
For Friendsgiving dinner, pair a halter or cowl-neck top with statement denim for a look that feels dressed up without going full party glam. For bar nights or weekend hangs, balance standout style with an outfit that fits the setting. Get inspired by what to wear to a bar for outfit ideas that work for everything from casual drinks to a livelier night out.
What Should I Wear for a Winter Night Out?
For a winter night out, build your look with pieces that bring the heat while giving you more coverage as temperatures drop. Try a long-sleeve mini or bodycon dress with knee-high boots, or pair a statement top and embellished denim with a faux fur jacket for dinner, drinks, or a night downtown. Gloves and chic layering pieces add extra warmth while keeping the finished outfit polished.
For holiday parties and club nights, turn up the glam with sparkle, plunging or open-back details, sleek boots, and long-sleeve styles that balance the season with after-dark appeal. Heading into New Year’s Eve? Explore Fierce and Sexy Clubwear for bold looks made for celebrating long after midnight.
Find a Going-Out Look That Feels Like You
The best going-out look fits your plans without losing your personality. Keep things casual with denim and a statement top, make getting dressed easy with a matching set, or go all-out in a mini that puts the focus on you. Windsor’s Going-Out Outfits give you the pieces to mix, match, experiment, and create a look for every mood—from laid-back fall hangs to glamorous winter celebrations.
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Retro Fab Patchwork Denim Bustier Top
Amp up your fab concert outfit with this trendy patchwork denim bustier top! Designed with a faded patchwork pattern on the denim fabric, you'll create that perfect retro look. The bustier is shaped with a sleeveless sweetheart neckline with a built-in padded underwire bust for a lifted effect and adjustable spaghetti straps for a customized fit. The smocked-back design provides added stretch. The fitted cropped hem will create an alluring snatched silhouette. Complete your 'fit with the matching mini skort or maxi skirt!
Shop Matching Bottoms: Retro Fab Patchwork Denim Mini Skort, Retro Fab High Slit Patchwork Denim Maxi Skirt
Fit & Features
- Denim fabric with faded patchwork design
- Sleeveless sweetheart neckline
- Built-in padded underwire bust
- Adjustable spaghetti straps
- Smocked back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2295
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Fab High Slit Patchwork Denim Maxi Skirt
Amp up your fab concert outfit with this trendy high slit patchwork denim maxi skirt! Designed with a faded patchwork pattern on the denim fabric, you'll create that perfect retro look. The skirt is shaped with a high waist leading to a maxi-length hem with a high-cut arched side slit on the slim-fit silhouette for an alluring vibe. Complete your 'fit with the matching bustier top!
Shop Matching Top: Retro Fab Patchwork Denim Bustier Top
Fit & Features
- Denim fabric with faded patchwork design
- High waist, front button and hidden zipper closure
- Maxi-length hem with high arched side slit
- Slim-fit silhouette
- Belt loops, front button closure
- Dual front and back pockets
- Runs true to size
Style Number/Barcode: 06601-0185
Category Name: Night Out
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Fab Reflective Chrome Shoulder Bag
This forever fab chrome shoulder bag is the ultimate accessory for festival season! Designed with a sleek faux leather material with a reflective chrome sheen, it features an angled rectangular-shaped design with fold-over flap closure and an adjustable shoulder strap with side buckle accents. The spacious lined interior is secure with a top zipper closure. Complete the look with the matching wedges and a layered necklace!
Shop The Matching Wedges: Forever Fab Reflective Chrome Wedge Heels
Fit & Features
- Faux leather material with chrome sheen
- Angled rectangular-shaped design
- Fold-over flap closure with dual magnetic button closures
- Adjustable shoulder strap with dual side buckles
- Zipper closure
- Woven-lined interior with single pocket
Style Number/Barcode: 07203-1943
Category Name: Night Out
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Undeniable Glow One-Shoulder Faux Pearl Mini Dress
Unlock an undeniable glow in this one-shoulder mini dress for your next night on the town! Showcasing faux pearl, rhinestone, and gemstone embellishments on lightweight mesh fabric, this party dress is here for the glamour girls. Features a flattering bodycon silhouette and a sassy mini-length hem. Complete the look in strappy heels and a clutch!
Fit & Features
- Faux pearl, rhinestone, gemstone embellishments
- Mesh fabric lined with stretchy knit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5384
Category Name: Night Out
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crush-Worthy Strapless Denim Bodycon Midi Dress
They'll all be crushing on you in the cutest denim bodycon midi dress! The cotton-blend denim fabric offers stretch and includes a comfy knit lining. This dress is shaped with a strapless scoop neckline featuring an angled design to accentuate your bust, with flexible boning at the bodice giving structure for a snatched look. The vertical seams down the front and back add a trendy touch to the curve-hugging silhouette. The back slit accent adds a sexy detail and allows for effortless movement. Style with a layered necklace and clear heels for your weekend plans!
Fit & Features
- Cotton-blend denim fabric with knit lining, moderate stretch
- Strapless angled scoop neckline
- Flexible boning
- Back zipper with hook and eye closure
- Back slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5453
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Season Staple Denim Print Faux Leather Stiletto Heels
Trendy with chic details, these denim print faux leather heels are a staple for the season. Designed with a medium-wash denim print on smooth faux leather material, these heels are a fabulous must-have! They feature an open square-shaped toe with a thin strappy design across the foot, thin adjustable ankle and heel straps with a buckle closure, and a stiletto heel. Pair with the matching shoulder bag for a seamlessly stylish 'fit!
Shop Matching Bag: Season Staple Denim Print Faux Leather Shoulder Bag
Fit & Features
- 4" Stiletto heel
- Faux leather material with medium-wash denim print
- Open square toe
- Thin strappy design
- Thin adjustable ankle and heel straps with buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4644
Category Name: Night Out
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elite Glam Faux Pearl Platform Block Heels
Showcase elite glamour at your next fancy affair in these faux pearl platform block heels! The faux leather heels feature all-over faux pearl embellishments for that trendy touch of sophistication. The open square-shaped toe has a wide toe strap, followed by thin adjustable ankle and heel straps with a buckle closure. The shoes are supported with a platform sole and a tall block heel. Style with the matching handbag for a chic seamless look!
Shop Matching Bag: Elite Glam Faux Pearl Mini Tote Handbag
Fit & Features
- 4.5" Block heel
- Faux leather material, mini faux pearls
- Open square toe
- Wide toe strap
- Thin adjustable ankle and heel straps with buckle closure
- Platform sole, padded insole
- Runs true to size
Style Number/Barcode: 07401-4645
Category Name: Night Out
Price: $12.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- 4.5" Block heel
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Dreamy Pearl And Rhinestone Trim Bustier Top
This gorgeously detailed pearl and rhinestone trim bustier top will give you a dreamy vibe for your party plans! It features a sleeveless sweetheart neckline with pleated mesh fabric at the bust, a rhinestone faux pearl-embellished chain trim under the bust and on the spaghetti straps, a corset-style bodice with a structured bust and flexible boning for a snatched silhouette, and a fitted, angled, and cropped hem. Complete your look with a midi skirt and metallic heels.
Fit & Features
- Sleeveless sweetheart neckline, pleated mesh at the bust
- Rhinestone and faux pearl-embellished chain trim
- Corset-style bodice, padded cups, structured underwire, flexible boning
- Adjustable spaghetti straps, back hook and eye closures
- Fitted, angled, and cropped hem
- Sheer mesh fabric, knit lining at the bust, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-5048
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Blooms Lace-Up Floral Chiffon Corset Top
Create a chic look for drinks with the girls in this lace-up floral chiffon corset top! The woven fabric features a floral chiffon burnout pattern for a pretty touch. The sleeveless square neckline has adjustable spaghetti straps for a customized fit, and the flexible boning inserts provide structure. The trendy lace-up designs at the sides give the top a sultry allure, leading to back hook and eye closures. The corset has a fitted, angled, and cropped hem for a snatched silhouette. Style with a mini skirt and mules.
Fit & Features
- Woven fabric with floral chiffon burnout pattern, knit lining, minimal stretch
- Sleeveless square neckline
- Adjustable spaghetti straps
- Flexible boning
- Lace-up sides, back hook and eye closures
- Fitted, angled, and cropped hem
- Runs true to size
Style Number/Barcode: 06003-2290
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sexy Sleek Tie-Front Cutout Satin Corset Top
This sexy sleek satin corset top will elevate your go-to date night look. The silky satin fabric has a chic sheen for a stunning allure. The top features a sleeveless square neckline with thin tank straps and a ruched bust with a cutout and tie-front design for a sultry detail. The flexible boning provides structure, while the smocked back allows moderate stretch. The corset top has a fitted, angled, and cropped hem for a snatched silhouette. Style with faux leather pants and strappy stilettos!
Fit & Features
- Satin woven fabric with knit lining, moderate stretch
- Sleeveless square neckline, thin tank straps
- Ruched bust
- Bust cutout with tie-front design
- Flexible boning, smocked back
- Fitted, angled, and cropped hem
- Runs true to size
Style Number/Barcode: 06003-2292
Category Name: Night Out
Price: $3.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleekin' Out Satin Strappy Mesh Bustier
Unleash your inner sleek diva in this sexy bustier for a night out! This statement bustier features a sweetheart neckline, adjustable spaghetti straps with a halter tie strap, a built-in underwire padded bust, and flexible boning for a flattering fit. The side ruched mesh panels and cropped hem add a touch of allure. Complete the look in high-rise flare pants for dinner and drinks!
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps, halter tie strap
- Back zipper and hook-eye closure, front hidden hook-eye fasteners
- Built-in padded underwire bust
- Flexible boning, side ruched mesh panels, cropped hem
- Lined satin fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06003-2291
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Diva Type Velvet Rhinestone Mini Dress
A velvet rhinestone mini dress for all the divas out there who love to shine! Capture the attention in this mini dress featuring a scoop neckline, adjustable spaghetti straps, and a flattering bodycon silhouette to flaunt your curves. Finish the look in platform heels for parties and going out!
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Bodycon silhouette, mini-length hem
- Back zipper and hook-eye closure
- Rhinestone embellished, velvet fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05103-5383
Category Name: Night Out
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Truth Be Bold Textered Lace-Up Mini Dress
The truth is, you'll be looking bold in this mini dress everywhere you go! Sultry and head-turning, this mini-length dress features a square neckline with a U-shaped metal insert, spaghetti straps that lace up in the back, and a flattering bodycon silhouette on textured mesh fabric with the perfect shimmer. Complete the look in glitter heels for extra sparkle.
Fit & Features
- Sleeveless square neckline
- U-shaped metal insert
- Spaghetti straps, lace-up back
- Bodycon silhouette, mini-length hem
- Textured mesh shiny fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05103-5380
Category Name: Night Out
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Flex Faux Leather Flare Pants
Make a major flex in these faux leather pants to showcase an elevated style! They feature a flattering V-cut mid-rise waist designed to give an hourglass effect, a hip-hugging fit, and a flared hem. Complete the look in a corset top for cocktail hour!
Fit & Features
- V-cut mid-rise waist
- Hip-hugging fit
- Flared hem
- Faux leather fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06502-2426
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxurious Twist Fishnet Sweater With Bralette
A luxurious twist on casual style! This sheer fishnet sweater top is crafted from a sheer metallic knit for an eye-catching and unique look with fitted long sleeves, a crew neckline, a cropped hem, and a detached faux leather triangle bralette to make this sweater stand out! Complete the look with trendy denim jeans for a weekend style.
Fit & Features
- Fitted long sleeves
- Crew neckline
- Cropped hem
- Sheer fishnet metallic knit fabric
- Detached faux leather bralette included
- Runs true to size
Style Number/Barcode: 06005-1831
Category Name: Night Out
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Night Out
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easily Darling Satin Floral Jacquard Bustier
Easy, breezy, and oh-so-darling! Envoke charm in this satin floral jacquard bustier featuring a sweetheart cowl neckline, adjustable spaghetti straps, and a built-in padded underwire bra for support. The flexible boning inserts and cropped hem provide a snatched and chic look with your favorite bottoms! Complete the look in a flirty skirt for a date or brunch!
Fit & Features
- Sleeveless sweetheart cowl neckline
- Adjustable spaghetti straps
- Stretchy smocked back, zipper and hook-eye closure
- Built-in padded underwire bra
- Flexible boning, cropped hem
- Floral jacquard print, satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2294
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Fab Patchwork Denim Mini Skort
Amp up your fab concert outfit with this trendy patchwork denim mini skort! Designed with a faded patchwork pattern on the denim fabric, you'll create that perfect retro look. It features a high waist and a mini-length asymmetric overlay over fitted shorts for a cool vibe. Includes a button-front closure and a back zipper. Complete your 'fit with the matching bustier top!
Shop Matching Top: Retro Fab Patchwork Denim Bustier Top
Fit & Features
- Denim fabric with faded patchwork design
- High waist, back zipper closure
- Mini-length asymmetric wrap-front overlay
- Fitted shorts
- Button front closure
- Back zipper closure
- Runs true to size
Style Number/Barcode: 06603-0365
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Radiance Rhinestone Strap Metallic Mules
Radiate all the glam vibes with these fabulous rhinestone strap metallic mules! Designed with faux leather material with a flashy metallic sheen, these mules feature an open square-shaped toe, a rhinestone-adorned strappy wide-banded design for extra shine, and a sturdy block heel. The open back offers effortless on-and-off styling. Complete your glitzy 'fit with the matching shoulder bag!
Shop Matching Bag: Glam Radiance Rhinestone Mesh Shoulder Bag
Fit & Features
- 4" Block heel
- Faux leather upper, padded insole
- Metallic sheen
- Open square toe
- Rhinestone strappy banded design
- Open back, on-and-off styling
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4643
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Along For The Ride Faux Leather Biker Jacket
Look edgy for the ride in this faux leather biker jacket whether you're a passenger or behind the wheel! Featuring a mock neckline with snap-button closure, long sleeves with zipper cuffs, a front zipper closure, faux zipper pockets, and a cropped hem with a snap-button strap, this cool faux leather jacket is the perfect way to take your style to the next level. Complete the look with knee-high boots.
Fit & Features
- Long sleeves, zipper cuffs
- Mock neckline, snap-button closure
- Front zipper closure, faux zipper pockets
- Cropped hem, snap-button closure strap
- Faux leather fabric, sewn-in woven lining
- Runs true to size
Style Number/Barcode: 06204-1869
Category Name: Night Out
Price: $59.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: M, L, XL, S
Product Badge:- Best Seller
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From The Garden Floral Embroidered Long Duster
Fresh from the garden! Arrive in this floral embroidered long duster to layer your outfit with chicness. It features fitted long sleeves, an open front design with a tie closure, and a flowy longline hem on sheer mesh fabric. Complete the look in simple block heels for a date night!
Fit & Features
- Fitted long sleeves
- Open front design, tie closure
- Flowy longline hem
- Floral embroidery
- Mesh fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06204-1686
Category Name: Night Out
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elite Glam Faux Pearl Mini Tote Handbag
Showcase elite glamour at your next fancy affair with this faux pearl mini tote handbag! The faux leather exterior features all-over faux pearl embellishments for that trendy touch of sophistication. The mini tote has a square-shaped design with sleek metal O-ring handles and an included chain-link shoulder strap for effortless wear. The bag features a magnetic button closure to secure your essentials in the spacious woven interior. Style with the matching platform block heels for a chic seamless look!
Shop Matching Shoes: Elite Glam Faux Pearl Platform Block Heels
Fit & Features
- Square-shaped design
- Faux leather exterior
- Mini faux pearls
- Dual metal O-ring handles
- Magnetic button closure
- Woven interior with a single pouch
- Attachable chain-link shoulder strap
Style Number/Barcode: 07204-0754
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Square-shaped design
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Pretty Shimmer Rhinestone Mesh Mini Party Dress
Give off the prettiest shimmer in this alluring rhinestone mesh mini party dress! The airy sheer mesh fabric is accented with all-over rhinestone embellishments for a gorgeous glam shine. The short dress features a sleeveless square neckline with adjustable spaghetti straps for a customized fit and a trendy asymmetric hanky hem with a flirty A-line silhouette. Style this mini dress with fringe earrings and metallic heels!
Fit & Features
- Sheer mesh fabric with knit lining, moderate stretch
- Round and rectangular-shaped rhinestones
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper, hook and eye closure
- Asymmetric hanky hem, A-line fit
- Runs true to size
Style Number/Barcode: 05103-5378
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Utterly Radiant Faux Pearl Bandage Crop Top
All you need to be utterly radiant is this faux pearl crop top! Designed on bandage seamless knit fabric that fits like a glove, this top features a strapless neckline with non-slip grip lining, faux pearl embellishments on the front, and a fitted crop hem. Complete the look with sleek faux leather pants for a rooftop bar lounge!
Fit & Features
- Strapless neckline
- Back zipper and hook-eye closure
- Faux pearl embellishments on the front
- Fitted crop hem
- Bandage seamless knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1834
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale