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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Fun And Flirty Halter Neck Skater Dress
This adorable skater dress is perf for twirling and giving off those fun and flirty vibes at your next party! It features a sleeveless deep V-neckline with halter straps that lead to a tie-back design, an open back, dual high waist seams, and a short skater skirt with a fab fit and flare silhouette. The plisse woven fabric includes a full knit lining. Complete your look with a lariat necklace and platform heels.
Fit & Features
- Sleeveless deep V-neckline
- Halter straps, tie-back design
- Open back
- Dual high waist seams
- Short skater skirt, fit and flare silhouette
- Plisse woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2908
Category Name: Night Out
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Velma Leopard Wrap Slit Mermaid Formal Dress
Special Occasion
Look and feel dangerously fierce and chic in the Velma leopard formal dress on your next dressy evening soiree! Crafted from an airy mesh fabric adorned with a leopard print and knit lining, this formal gown is alluring. She features a sweetheart neckline and adjustable spaghetti straps, padded bra cups provide comfortable support, while the high front wrap slit adds a touch of sophistication to the floor-length mermaid silhouette. Complete the look with earrings, a clutch, and heels.
Fit & Features
- Leopard print, mesh fabric lined with stretchy knit
- Sweetheart neckline
- Padded bra cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- High front wrap slit
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05002-8483
Category Name: Night Out
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Allure Ruched Mesh Corset Mini Dress
Show off a stunning allure in this iconic corset mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, this sultry dress offers an airy lightweight feel perfect for the warmer months. The mini-length dress is shaped with a sleeveless sweetheart neckline, a chic corset bodice hidden under the mesh, and adjustable spaghetti straps for your perfect customized fit. The ruched side and back seams will accentuate your gorgeous curves on the bodycon silhouette. Complete your look with strappy stilettos.
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Sweetheart neckline, padded bra cups
- Hidden corset bodice
- Adjustable spaghetti straps, back zipper hook-eye closure
- Ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5546
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Bae High-Rise Faux Leather Midi Skirt
With this faux leather midi skirt, you'll be looking like bae! Designed from a sleek lightweight faux leather fabric, this midi-length skirt offers a flattering high-rise waist, a front slit for movement, and a form-hugging silhouette that accentuates your curves. Complete the look in a strapless corset top and sandals for evening plans!
Fit & Features
- Faux leather fabric with sewn-in knit lining
- Moderate stretch
- High-rise waist
- Front slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 06501-0971
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Short Faux Leather Paperbag Shorts
Keep it short and sweet this season in these faux leather shorts! They feature a paper bag high-rise waist for a flattering fit with an adjustable belt and side pockets for keeping your hands warm. With a cuffed hem and faux leather fabric, these shorts are both trendy and versatile for year-round styling. Complete the look in a smooth basic top.
Fit & Features
- High-rise paper bag waist
- Adjustable belt, hidden zipper and hook closure
- Side pockets, belt loop accents
- Cuffed hem
- Faux leather lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0403
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Got The Look Satin High-Rise Cargo Joggers
These satin cargo joggers will make everyone say she's got the look! The pants feature a high-rise waist with an elasticized back band ensuring a perfect fit while the side and cargo flap pockets provide functional convenience. The jogger style silhouette and elasticized hem add a trendy touch to these must-have joggers. Style with a crop top for weekend plans!
Fit & Features
- High-rise waist, elasticized backband
- Side pockets, front button and zipper closure
- Cargo flap pockets
- Jogger style silhouette
- Elasticized hem
- Smooth satin fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06402-1378
Category Name: Night Out
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Mesh Strapless Bodycon Mini Dress
Enter looking like chic in this mesh mini dress for a night on the town! The dress is crafted from a textured mesh fabric designed in a strapless and bodycon silhouette complete with a sassy cutout back and mini-length hem. Style this dress with statement earrings.
Fit & Features
- Textured mesh lined fabric, moderate stretch
- Strapless neckline
- Cutout back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5542
Category Name: Night Out
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bringing The Vibe Zipper Ponte Mini Skort
Bring the edgy vibe in this ponte mini skort to casual hangouts! The high-rise waist and bodycon fit flatter your curves, while the dual front zip-up closures add a touch of edginess. Crafted with comfortable ponte fabric, this mini-length skirt comes with shorts lining. Complete the look with a bomber jacket and your fave sneakers!
Fit & Features
- Ponte fabric, no stretch
- High rise waist
- Dual front and side zipper closures
- Bodycon fit
- Shorts lining
- Runs true to size
Style Number/Barcode: 06403-0404
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Posh On The Scene Strapless Plaid Skort Romper
Arrive on the scene in this strapless plaid romper for a posh vibe! The strapless neckline and form-hugging silhouette accentuate your curves while the front skirt overlay with slit adds a touch of flirtiness over the shorts lining on textured plaid knit fabric. Complete the look with a sassy crop jacket and boots for a dressy birthday brunch!
Fit & Features
- Strapless straight neckline
- Back zipper, hook and eye closure
- Form-hugging silhouette
- Front skirt overlay, slit accent
- Shorts lining
- Textured plaid knit fabric, knit bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1111
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Femme Perfection Satin Lace Corset Top
Dare to be femme in this satin lace corset top for a look that's confident and perfect! With a square neckline, underwire bust, and adjustable spaghetti straps, this top will showcase your curves and enhance your figure. The flexible boning and multiple hook and eye fasteners provide a perfect, secure fit while the sheer lace front panel shows some skin. Complete the look in women's best-selling bottoms!
Fit & Features
- Sleeveless square neckline, adjustable spaghetti straps
- Underwire bust, sheer lace panel
- Flexible boning, curved cropped hem
- Multiple back hook and eye fasteners
- Lined satin fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06003-2373
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Going Everywhere Belted Faux Suede Skort
Take this faux suede skort everywhere you go for total vibes! The high-rise folded belted waist adds a chic touch while providing a flattering fit. With a form-hugging silhouette and built-in shorts lining, you can confidently go anywhere and do anything in style. Complete the look in a short sleeve bodysuit and sandals.
Fit & Features
- Faux suede fabric, minimal stretch
- High-rise waist
- Form-hugging silhouette
- Shorts lining
- Runs true to size
Style Number/Barcode: 06403-0398
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Own The Room Strappy V-Neck Flare Jumpsuit
Own the room in this sassy jumpsuit with the girls! Showcasing a sexy plunge V-neckline and form-hugging fit, this jumpsuit accentuates your figure for a show-stopping look. The strappy open back and flared hem add a touch of playfulness to the stretchy rib knit fabric. Complete the look in stiletto sandals and earrings!
Fit & Features
- Stretchy rib knit fabric
- Spaghetti straps
- Strappy open back
- Form-hugging fit
- Flare hem
- Runs true to size
Style Number/Barcode: 06502-2463
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Captivating Shine Rhinestone Fringe Earrings
Captivate with luxe shine in these gorgeous rhinestone fringe earrings! Embellished with glimmering mini rhinestone embellishments, these earrings feature a twisted asymmetric top design with multiple rows of cascading fringe. Include a post-back closure. Style with your classic LBD and strappy stilettos to add some sparkle on your next night out.
Fit & Features
- Twisted asymmetric design
- Multiple rows of fringe
- Rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1903
Category Name: Night Out
Price: $3.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Sophistication Strappy Platform Block Heels
Flirty fun meets sophistication in these patent block heels that dare to steal the show! Featuring an almond toe, strappy design, and platform sole, these heels add stylish height. The dual ankle straps and buckle closure provide a secure fit while the cushions at the ball of the foot ensure comfort. Complete the look in a pretty skater dress for a soiree or event!
Fit & Features
- 3" Block Heel
- Almond toe
- Strappy design
- Platform sole, luxe fit cushions at ball of foot
- Dual ankle straps, buckle closure
- Patent leather material
- Runs true to size
Style Number/Barcode: 07401-4723
Category Name: Night Out
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flashy Glam Rhinestone Fringe Front-To-Back Earrings
Radiate a flashy glam vibe in these fabulous rhinestone fringe front-to-back earrings! They feature a curved horizontal bar post embellished with round rhinestones and a chic angled rhinestone, a hanging curved horizontal bar with rhinestones, and a multi-row rhinestone fringe cascading design for all the sparkle. Include a post-back closure. Style these trendy earrings with a cuff bracelet.
Fit & Features
- Front-to-back earring design
- Curved horizontal bar post
- Round rhinestones and angled rhinestone
- Hanging curved horizontal bar with rhinestones
- Multi-row rhinestone fringe
- Post-back closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1904
Category Name: Night Out
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love It Lace-Up Satin Cropped Corset Top
You'll love the iconic look of this silky satin cropped corset top! Designed with a sleek satin woven fabric, this top features a sleeveless sweetheart neckline for a feminine vibe, adjustable spaghetti straps offering a customized fit, secure hook and eye closures at the front, and flexible boning inserts. The cutout lace-up sides add a sultry touch, while the fitted cropped hem will create a snatched silhouette. Pair with high-rise jeans and sneakers for a casual-chic style.
Fit & Features
- Satin woven fabric with minimal stretch
- Sweetheart neckline
- Adjustable spaghetti straps
- Cutout lace-up sides
- Front hook and eye closures, flexible boning
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2367
Category Name: Night Out
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essential Sweetie Off-The-Shoulder Tube Crop Top
Versatile and essential, this tube crop top makes getting ready for last-minute plans a breeze! Crafted from soft, stretchy, rib knit fabric this top offers a sweet folded off-the-shoulder neckline adorned with short sleeves and a fitted crop hem to flaunt your figure. Complete the look with high-rise jeans and sandals for a trend-worthy outfit!
Fit & Features
- Stretchy, soft rib knit fabric
- Folded off-the-shoulder
- Short sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1923
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dream Of Sparkle Rhinestone Chandelier Earrings
Create the dreamiest look that will radiate sparkly vibes in these rhinestone chandelier earrings! They feature a gorgeously glam chandelier design with a round clear rhinestone stud, mini iridescent rhinestone fringe for that multi-colored shine, and baguette-shaped clear rhinestone fringe at the center. Include a post-back closure. Style with a dainty bracelet.
Fit & Features
- Chandelier design
- Round clear rhinestone stud
- Iridescent rhinestone fringe
- Baguette clear rhinestone fringe
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1897
Category Name: Night Out
Price: $3.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instant Classic Aviator Sunglasses
These sleek aviator sunglasses will be an instant classic and staple for the season! They feature a traditional aviator design with tinted lenses, a thin metal frame with thin arms, a brow bar and nose bridge, and rubber nose pads for support. Style these sunnies with a denim jacket for that casual-cool vibe.
Fit & Features
- Aviator design
- Tinted lenses
- Thin metal frame and arms
- Thin brow bar and nose bridge
- Rubber nose pads
Style Number/Barcode: 07008-1046
Category Name: Night Out
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Design Faux Leather Mini Skort
The sleek design of this faux leather mini skort will amp up your fave going-out looks! Made with a coated faux leather fabric, this trendy skort features a high waist, a front mini-length overlay with a chic double slit design to add some allure, and fitted shorts. Style with a corset top and mules for a rooftop bar!
Fit & Features
- Coated faux leather fabric
- High waist
- Front mini-length overlay
- Double slit design
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-0396
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Floral Ruched Mesh Mini Dress
Walk into any party looking like a dream in this floral ruched mesh mini dress! The bold multi-colored floral print will capture all the attention, while the airy mesh fabric offers breezy comfortable wear. The mini-length dress features a sleeveless square neckline with adjustable spaghetti straps for a customized fit. The trendy ruched detailing down the side seams will accentuate your curves along the alluring bodycon silhouette. Style this short dress with hoop earrings and clear heels.
Fit & Features
- Floral print
- Sheer mesh, sewn-in knit lining
- Sleeveless square neckline
- Spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5534
Category Name: Night Out
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Treasure Strapless Linen Corset Top
Everyone will be asking where you found this trendy linen crop corset top! You'll love the sweetheart neckline and padded bra cups for a flattering fit, while the non-slip grip lining, multiple back hook and eye fasteners, and flexible boning keep it in place. Complete the look with the matching wide-leg pants.
Shop Matching Bottoms: Trendy Treasure Linen Wide-Leg Pants
Fit & Features
- Linen-blend fabric, sewn-in knit lining, no stretch
- Strapless sweetheart neckline
- Multiple back hook and eye fasteners
- Padded bra cups, flexible boning
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2365
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Aesthetic Plaid Wrap Skort
Create the perf chic aesthetic for everyday with this plaid wrap skort! Designed with an iconic plaid print on woven fabric, it features a high-rise waist, an asymmetric faux wrap-front design with a mini-length hem, and fitted shorts. Style with a basic crop top, a faux leather moto jacket, and ankle booties!
Fit & Features
- High-rise elasticized waist
- Asymmetric faux wrap-front design, mini-length hem
- Fitted shorts
- Plaid print
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0393
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Plaid Babe High Rise Slit Skort
Preppy with babe status! This plaid skort features a high-rise waist, a front skirt overlay with a slit design, and a flattering form-hugging fit and mini-length hem. Complete the look in a basic tee and denim jacket.
Fit & Features
- High-rise waist
- Back zipper closure
- Front skirt overlay, slit design
- Form-hugging fit, mini-length hem
- Shorts lining
- Plaid pattern, texture knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-1108
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale