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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Iconic Elegance Off The Shoulder Jumpsuit
Channel iconic elegance with a sleek jumpsuit! The jumpsuit features an off-the-shoulder neckline, a tiered ruffled popover accent, short sleeves, and a straight leg fit with a flared hem. Complete look with wedges and hoops.
Fit & Features
- Off the shoulder neckline
- Tiered ruffled popover
- Short sleeves
- Straight leg, flared hem
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0591
Category Name: Night Out
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Sequins Cropped Bustier
Keep it sassy with a sparkling sequin bustier! The bustier features sequins, a sleeveless sweetheart neckline, padded cups, bungee spaghetti straps, and a cropped hem. The bustier is composed of a lined mesh fabric that offers a form hugging fit with minimal stretch. Complete look with the matching mini skirt.
Shop Matching Mini Skirt: Sassy Sequins High Waist Skirt
Fit & Features
- Sleeveless sweetheart neckline
- Padded cups
- Bungee spaghetti straps
- Cropped hem
- Sequins
- Lined mesh fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06001-3459
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Sequins High Waist Skirt
Keep it sassy with a sparkling sequin skirt! The skirt features a high-rise waist, dazzling sequins, and a mini-length silhouette. The skirt is composed of a lined mesh fabric that offers a form hugging fit with minimal stretch. Complete look with the matching bustier.
Shop Matching Bustier: Sassy Sequins Cropped Bustier
Fit & Features
- High rise waist
- Sequins
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0433
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glow And Go Rhinestone Belt
Get ready to glow and go, babe! The belt features a rhinestone band and a U-shaped metal buckle. Complete look with a trench and mules.
Fit & Features
- Rhinestones
- U-shaped metal buckle
Style Number/Barcode: 07301-0306
Category Name: Night Out
Price: $10.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lady Luck Faux Suede Block Heels
Create your own luck with these statement heels! They feature a closed-back, an adjustable asymmetrical ankle strap, an open almond toe with sleek straps over the toe, and a block heel. The heels are composed of a faux suede material. Complete look with an LBD.
Fit & Features
- Closed-back
- Adjustable asymmetrical ankle strap
- Open almond toe
- Straps over the toe
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2879
Category Name: Night Out
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Chic Plaid Belted Faux Wool Jacket
Keep it timelessly chic in a plaid coat that is perf for the season! The plaid jacket features a collared neckline, long sleeves, a double breast button closure, faux front pockets, an adjustable belt with a square-shaped buckle, and a mid-thigh length. The jacket is is composed of a faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with ankle booties.
Fit & Features
- Plaid print
- Collared neckline
- Long sleeves
- Double-breast button closure
- Faux front pockets, adjustable belt
- Mid-thigh length
- Faux wool, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0230
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Moment Sherpa Knit Shacket
Create a cozy moment in a shacket that keeps it casual and stylish. The shacket features a collared neckline, a multi-button down front, two chest pockets with single-button closure, long sleeves, and a longline length with rounded hem. The shacket is composed of a faux sherpa knit fabric that offers a relaxed fit with minimal stretch. Complete look with a scarf and ankle booties.
Fit & Features
- Collared neckline
- Multi-button down front
- Two chest pockets with single-button closure
- Longline length with rounded hem
- Faux sherpa knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0232
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Essential Fleece Trench Coat
Layer up in this essential trench coat that elevates your style. The trench features a collared neckline with lapel accent, long sleeves, lightly padded shoulders, a single button closure, a tie waist belt, and a longline length. The trench is composed of a lined fleece fabric that offers a relaxed fit with minimal stretch. Complete look with boots.
Fit & Features
- Collared neckline with lapel accent
- Long sleeves, lightly padded shoulders
- Single-button closure, tie-waist belt
- Longline length
- Lined fleece fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0227
Category Name: Night Out
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Essential Faux Fur Bolero Jacket
Add a touch of luxury to your ensemble with this elegant faux fur crop jacket. Its plush fabric gives an opulent feel, perfect for adding sophistication to any look. The jacket's cropped length makes it a chic pairing with cocktail dresses, formal jumpsuits, or dressy pants ensembles. With its clean, collarless design and discreet front fastening, this jacket offers a modern take on classic bolero styling.
Fit & Features
- Draped open front
- Long sleeves
- Cropped hem
- Soft faux fur fabric
- Satin-like woven lining
- No stretch
- Runs true to size
Style Number/Barcode: 06201-0229
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Heartbreaker Mesh Midi Dress
This midi dress will break some hearts and leave an unforgettable impression! The bodycon dress features a sleeveless sweetheart neckline, contrast piping, adjustable spaghetti straps, a high side slit for a sexy display of leg, and ruching throughout that enhances your natural curves. Complete the look in this mid-length dress with mules and a sleek clutch.
Fit & Features
- Sleeveless sweetheart neckline, contrast piping at the bodice
- Adjustable spaghetti straps
- Back zipper, hook-eye closure
- High side slit
- Ruched sheer mesh-lined fabric, moderate stretch
- Midi-length silhouette, form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-1269
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show off Chain Block Heels
Show off your flawless style in these bomb heels! The PU heels feature an open square toe, a single PVC toe strap and a gold chain detail around the ankle. Pair them with a sexy mini dress and hoops for the perfect GNO look.
Fit & Features
- PU material
- PVC toe strap
- Block heel
- Chain ankle strap
- Runs true to size
Style Number/Barcode: 07401-2876
Category Name: Night Out
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Stunner Lace-Up Faux Leather Heels
Lace-up in glam stilettos that take your look to the next level! The heels feature lace-up straps, an open square toe with a strappy caged design, and a sleek stiletto heel. The heels are composed of a faux leather material. Complete the look with an LBD for your GNO!
Fit & Features
- Lace-up straps
- Open square toe
- Strappy caged design
- Stiletto heel
- Faux leather material
Style Number/Barcode: 07401-2875
Category Name: Night Out
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lead On Snake Print Platform Stilettos
Lead the way with stylish heels that keep you on-trend! The heels feature a closed-back, an adjustable ankle strap, an open almond toe with a strap over the toe, platform, stiletto heel, and a snake print. Complete the look with an LBD and statement earrings.
Fit & Features
- Adjustable ankle strap
- Open almond toe
- Strap over the toe
- Platform
- Stilleto heel
- Snake print
Style Number/Barcode: 07401-2867
Category Name: Night Out
Price: $15.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Impressions High Slit Maxi Skirt
Make a bold impression with a maxi skirt that brings the drama! The skirt features a high rise waist, a high side slit, and a maxi-length silhouette. Complete look with the matching crop top and heels.
Shop Matching Crop Top: Bold Impressions One Shoulder Crop Top
Fit & Features
- High rise waist
- High side slit
- Maxi length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06501-0434
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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City Life PVC Thong Heels
Grab the girls and head out for a night on the town in these fab heels! The heels feature an open back, an open square toe, a PVC thong strap and a clear block heel. Style them with a bodycon dress and a matching bag.
Fit & Features
- Clear block heel
- Square toe
- PVC thong strap
- Runs true to size
Style Number/Barcode: 07401-2874
Category Name: Night Out
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Illusion Stripe Faux Fur Jacket
Stay on trend with a jacket that is part casual, part glam! The jacket features a collared neckline, a zipper front with multi-button closure, long sleeves, side pockets, and an illusion stripe design. Complete look with a bustier and high waist jeans.
Fit & Features
- Collared neckline
- Zipper front, multi-button closure
- Long sleeves
- Side pockets
- Illusion stripe design
- Faux fur fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06201-0220
Category Name: Night Out
Price: $18.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Chic Faux Fur Jacket
Keep it casually chic with a fab jacket to nail those effortless vibes! The jacket features a collared neckline, long sleeves, a multi-row hook and eye closure, long sleeves, hidden side pockets, and is composed of a lined faux fur fabric. The jacket offers a relaxed fit with minimal stretch. Complete the look with a bodysuit and boyfriend jeans.
Fit & Features
- Collared neckline
- Long sleeves
- Multi-row hook and eye closure
- Hidden side pockets
- Lined faux fur fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0223
Category Name: Night Out
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Timeless Sophistication Belted Faux Wool Coat
Keep it timelessly chic with a coat that layers perfectly over your dressy outfits! The coat features a collared neckline with lapel accents, long sleeves, a cinching tie waist belt with belt loops, and hidden side pockets. The coat is composed of an unlined faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with a cabby hat and thigh-high boots.
Fit & Features
- Collared neckline with lapel accents
- Long sleeves
- Tie waist belt with loops
- Hidden side pockets
- Faux wool fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0224
Category Name: Night Out
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Getting The Ponte Across Halter Corset
Get your point across with a stunning corset that makes a wowing statement! The corset features a halter neckline, criss-cross straps at the neck, a mini cutout at the bodice, and corset seams with flexible boning. Complete look with a high waist skirt and mules.
Fit & Features
- Halter neck
- Criss-cross straps at neck
- Mini cutout
- Corset seams, flexible boning
- Cropped hem
- Ponte knit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06001-3445
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Sultry Satin Corset Top
Stunning and sultry, this sleek satin corset top is perf for date night! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a corset-designed front with a structured bust, a lattice front detail, and a mid-length flirty peplum hem. Style this top with your fave distressed jeans and chic mules.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps, back zipper and hook and eye closure
- Corset-designed front, structured bust
- Lattice front detail
- Mid-length peplum hem
- Satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1400
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Pleats Satin Cropped Corset
Keep it pretty in pleats with a corset that brings major glam to your look! The corset features a plunging sleeveless V-neckline, pleated bust, corset seams with flexible boning, shoulder straps, and a cropped hem. The top is composed of a satin fabric that offers a form hugging fit with minimal stretch. Complete look with high waist pants.
Fit & Features
- Sleeveless V-neckline
- Pleated bust
- Corset seams, flexible boning
- Shoulder straps
- Cropped hem
- Satin fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06003-1397
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry Details Chainlink Bodysuit
Bring the sultry details with a sleek bodysuit that brings eye-catching details! The bodysuit features a plunging V-neckline, chainlink straps that cross at the bodice, a sexy cutout, and a thong bottom. The bodysuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with high waist jeans and mules.
Fit & Features
- Sleeveless V-neckline
- Chainlink straps, cross at bodice
- Cutout
- Spaghetti straps
- Thong bottom
- Smooth knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 06001-3447
Category Name: Night Out
Price: $4.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glam Life Faux Fur Jacket
Live out that glam life with a jacket that elevates your cold-weather outfits. The jacket features a collared neckline with a lapel accent, a multi-snap button closure, long sleeves, lined side pockets, and a mid-length hem. The jacket is composed of a lined faux fur fabric that offers a relaxed fit with minimal stretch. Complete look with boots.
Fit & Features
- Collared neckline, lapel accent
- Multi-snap button closure
- Long sleeves
- Lined side pockets
- Lined faux fur
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0213
Category Name: Night Out
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Stylish Stunner Platform Block Heels
Yes babe, you'll be such a stylish stunner in these trendy platform block heels! They feature an open square toe with a thin strap, a thin adjustable ankle strap with a chic buckle detail, a platform, and a tall block heel. Style these must-have heels with a cute clutch.
Fit & Features
- Open square toe with a thin strap
- Thin adjustable ankle strap, buckle detail
- Closed back
- Platform
- Block heel
- Faux nubuck material
- Runs true to size
Style Number/Barcode: 07401-2862
Category Name: Night Out
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance