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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High Waist Tweed Knit Mini Skirt
Keep it trendy in a high waist mini skirt that slays. The skirt features a high rise waist, a mini side slit and composed of a tweed knit fabric. Complete look with a ribbed crop top.
Fit & Features
- High rise waist
- Mini side slit
- Tweed knit fabric
- Form hugging fit
Style Number/Barcode: 06401-0258
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slay In Basics Ribbed Knit Mini Dress
Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Mock neck
- Long sleeves
- Rounded mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0852
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flocked Floral Mesh Bodysuit
This flocked floral mesh bodysuit would be perfect for a date night out with bae! It features long fitted sleeves, a form-fitting style, a sheer mesh fabric that offers plenty of stretch, and has an allover velvet flocked floral print. Pair this bodysuit with a faux leather mini skirt and thigh high boots.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Thong bottom with dual snap button closures
- Form-hugging fit
- Sheer mesh fabric with plenty of stretch
- Allover velvet flocked floral print
Style Number/Barcode: 06001-2947
Category Name: Night Out
Price: $13.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Patent Pointed-Toe Lucite Block Heel Booties
Show off a chic new look in these stunning patent pointed-toe booties! They feature a trendy clear lucite block heel and a sleek patent finish. Wear with your fave crop top and mom jeans to amp up your casual look.
Fit & Features
- Pointed-toe
- Inner zipper closure
- Lucite block heel
- Patent material
Style Number/Barcode: 07403-0385
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Clearly On Trend Block Heels
Clearly these buckle detail block heels are on trend! They feature a chic clear toe strap and a stylish buckle accent. Pair these heels with distressed denim to elevate an everyday casual look.
Fit & Features
- Open almond toe
- Clear PVC toe strap
- Adjustable around the ankle strap with buckle detail
- Closed back
- Block heel
- Faux nubuck material
Style Number/Barcode: 07401-2440
Category Name: Night Out
Price: $7.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Level Up Platform Block Heel Booties
Level up your look in these chic block heel booties! Featuring a stylish platform and a sleek block heel, these booties are perfect for your next party. Simply pair them with a LBD and stunning statement earrings for a gorgeous look.
Fit & Features
- Almond toe
- Platform
- Thin block heel
- Dual zipper detailing
- Faux nubuck material
Style Number/Barcode: 07403-0380
Category Name: Night Out
Price: $21.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Viva La Velvet Biker Shorts
Live it up in velvet biker shorts to glam up any outfit! Style with a cute crop top or oversize tee-shirt for a look that's ready to go! The biker shorts feature a high rise waist, a mid-thigh length, and composed of luxe velvet fabric.
Fit & Features
- High rise waist
- Mid-thigh length
- Velvet fabric
- Form hugging fit
Style Number/Barcode: 06503-0184
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry And Stunning Snake Print Mini Skirt
Look ever so sultry and stunning in this on-trend snake print mini skirt! It features a flattering high rise waist and an overall form-hugging fit to enhance your curves. Pair this skirt with trendy clear mules for your next night out with the girls.
Shop Matching Top: Sultry And Stunning Snake Print Crop Top
Fit & Features
- High rise waist
- Short, form-fitting style
- Allover snake print
- Mesh fabric
Style Number/Barcode: 06501-0310
Category Name: Night Out
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Style Faux Nubuck Block Heels
Get wrapped in style with these chic heels that dress up all your best outfits! The heels feature an open back, wrap-around straps, an open square toe, a wide strap over the toe, and a narrow block heel. Complete look with a wrap mini dress and laritat necklace.
Fit & Features
- Open back
- Single strap over the back of the ankle
- Wrap-around straps
- Open square toe
- Wide strap over the toe
- Narrow block heel
- Faux nubuck material
Please be advised that these heels run small, purchase one size up.
Style Number/Barcode: 07401-2438
Category Name: Night Out
Price: $16.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed and Fierce Faux Nubuck Block Heels
Keep it fierce in heels that let you unleash your inner fashionista. The heels feature an adjustable ankle strap, a trendy narrow block heel, an open square toe with a single strap over the toe. Complete your trendsetting look with a bodycon dress and a cropped blazer.
Fit & Features
- Adjustable ankle strap
- Closed-back
- Open square toe
- Single strap over the toe
- Narrow block heel
- Faux Nubuck material
- Available in Leopard print and Natural
Style Number/Barcode: 07401-2442
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Velvet High Rise Joggers
Showcase a luxe look at your holiday party in these velvet high rise joggers! They feature a high rise banded waist with a tie front, side pockets, and a relaxed fit through the legs with a banded jogger hem. Pair these bottoms with a chic cropped blouse and your fave hoop earrings.
Fit & Features
- High rise banded waist
- Tie front
- Side pockets
- Relaxed fit through the legs
- Banded jogger hem
- Ribbed velvet fabric
Style Number/Barcode: 06502-0469
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Fab Knee High Stiletto Heeled Boots
You'll be feelin' oh-so-fab in these chic stiletto heeled boots! They feature a knee high design with a croc embossed print and a faux leather material. Pair these sleek boots with dark wash skinny jeans for a must-have fall look.
Fit & Features
- Knee high design
- Inner zipper closure
- Pointed toe
- Stiletto heel
- Faux leather material
- Croc embossed print
Style Number/Barcode: 07402-0203
Category Name: Night Out
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry And Stunning Snake Print Crop Top
Look ever so sultry and stunning in this on-trend snake print crop top! It features a mock neckline and an overall form-hugging fit to enhance your curves. Pair this top with trendy clear mules for your next night out with the girls.
Shop Matching Bottoms: Sultry And Stunning Snake Print Mini Skirt
Fit & Features
- Mock neckline
- Long fitted sleeves
- Cropped
- Front ruched detailing with ties that close at back
- Allover snake print
- Mesh fabric
Style Number/Barcode: 06001-2943
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Edgy Block Heel Booties
Get an effortlessly edgy look in these faux nubuck block heel booties! They feature an ankle-high design with a chunky lug sole and a tall, sturdy block heel. Pair these booties with dark wash skinny jeans and an oversized sweater for major fall vibes.
Fit & Features
- Ankle-high design
- Round toe
- Inner zipper closure
- Lug sole
- Block heel
- Faux nubuck material
- Partial elastic detail at ankle
Style Number/Barcode: 07403-0386
Category Name: Night Out
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Chic Stiletto Booties
Stylish and oh-so-chic, these stiletto booties are a must-have for a night out with the girls! They feature an open toe design with a sexy stiletto heel. Pair these booties with a curve-hugging bodycon dress for a gorgeous look from head to toe.
Fit & Features
- Open toe
- Dual front cut outs
- Sleek stiletto heel
- Back zipper closure
- Above the ankle height
- Faux nubuck material
Style Number/Barcode: 07403-0382
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Trendsetter Zebra Print Stiletto Heels
Get ready to strut in these zebra print stilettos and you'll be the major trendsetter of your squad! Featuring a wrap-around ankle design and a bold zebra print, pair these heels with a simple yet stunning mini dress for your next night out.
Fit & Features
- Open almond toe with a toe strap
- Strappy design with double adjustable ankle straps
- Open back
- Sleek stiletto heel
- Faux leather material
- Zebra print
Please be advised that these heels run small. Fit model recommends one size up.
Style Number/Barcode: 07401-2439
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Twist Back Ribbed Knit Midi Sweater Dress
Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Open back with twist back detail
- Mid-length silhouette
- Form-hugging fit
- Ribbed sweater knit fabric
Style Number/Barcode: 06005-0846
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flutter Some Hearts Mesh Crop Top
You'll be sure to flutter some hearts in this chic mesh crop top! It features a high crew neckline, long sleeves with puff shoulders, a cropped, fitted style, and is composed of a sheer mesh fabric with all-over butterfly appliques. Pair this top with high rise denim to dress it down or a faux leather mini skirt for a night out.
Fit & Features
- High crew neckline
- Long sleeves with puff shoulders
- Complete back zipper and hook and eye closure
- Cropped, fitted style
- Sheer mesh fabric
- All-over butterfly appliques
- No stretch
Style Number/Barcode: 06003-1123
Category Name: Night Out
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Cozy Vibes Duster
Get major cozy vibes in this adorable flowy duster! It features long fitted sleeves, a mid-length flowy fit and a textured knit fabric. Complete your loungewear look with chic slides for the ultimate stay at home 'fit.
Shop Matching Top: Major Cozy Vibes Cropped Tank
Shop Matching Bottoms: Major Cozy Vibes Wide Leg Pants
Fit & Features
- Long fitted sleeves
- Mid-length hem
- Flowy, relaxed fit
- Textured knit fabric
Style Number/Barcode: 06202-0117
Category Name: Night Out
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Cozy Vibes Cropped Tank
Get major cozy vibes in this adorable cropped tank! It features a flattering scoop neckline, a majorly cropped hem and a textured knit fabric. Complete your loungewear look with chic slides for the ultimate stay at home 'fit.
Shop Matching Duster: Major Cozy Vibes Duster
Shop Matching Bottoms: Major Cozy Vibes Wide Leg Pants
Fit & Features
- Tank-like shoulder straps
- Scoop neckline
- Cropped hem
- Form-hugging fit
- Textured knit fabric
Style Number/Barcode: 06001-2938
Category Name: Night Out
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fashionista Moment Mini Croc Crossbody Purse
This purse is for the fashionistas out there looking to make a chic statement! Perfect for a brunch date or fab night out, this mini purse is the one! The purse features top handles, a fold-over closure, and a mini square design. Complete your look with a sleek bodysuit and high waist jeans.
Fit & Features
- Mini square design
- Fold-over closure
- Double handles
- Detachable shoulder strap
- Croc-embossed design
- Faux leather material
Style Number/Barcode: 07201-0043
Category Name: Night Out
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold and Fierce Leopard Print Crop Top
Strike a bold look in this crop top that slays! The top features a bold leopard print, a high round neckline, shoulder pads, and a cropped hem. Complete your look with high waist leggings.
Fit & Features
- High round neckline
- Sleeveless
- Shoulder pads
- Leopard print
- Cropped hem
- Brushed woven fabric with moderate stretch
Style Number/Barcode: 06003-1121
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Reign N' Shine Rhinestone Bustier
Reign the night with a sparkling bustier that puts you in the spotlight! The bustier features a sleeveless sweetheart neckline, padded push-up cups, removable and adjustable spaghetti straps, a dazzling sequin and rhinestone embellished bodice, a sheer mesh insert under the bust with contrast flexible boning, a cropped hem, and back hook and eye closures. Complete your party look with a high waist mini skirt.
Fit & Features
- Sleeveless sweetheart neckline
- Padded push-up cups
- Removable and adjustable spaghetti straps
- Sequin and rhinestone embellishments
- Sheer mesh insert under the bust, contrast flexible boning
- Cropped hem, back hook and eye closures
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1125
Category Name: Night Out
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chrome Cutie Block Heels
Keep it chic in chrome heels that will create head-turning looks! The heels feature a chrome finish, an open almond toe with a single strap over the toe and a sturdy block heel. Complete your outfit with a stunning formal dress.
Fit & Features
- Narrow adjustable ankle strap
- Open almond toe with a single strap over the toe
- Closed-back
- Block heel
- Chrome finish
Style Number/Barcode: 07401-2433
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale