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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Side Slit Mini Skirt
Slide on this mini skirt for a sultry look! It features a high rise waist, double front vetical seams, and a short hem with a slit. The knit fabric offers moderate stretch and a form hugging fit.
Black: Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-0237
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cut Out For This One Shoulder Mini Dress
This dress is made for that GNO you got planned! It's time to party bb girl!
Fits & Features
- Fitted One Shoulder Long Sleeve
- Slanted Neckline
- Waist Cut Out
- Mini Length Silhouette
- Stretchy Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-1165
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitz And Glamour Satin Bustier
Bring the glitz and glamour to your date night look with this sexy satin bustier! It features rhinestone thin shoulder straps, a sweetheart neckline with rhinestone trim, padded cups with underwire, and a cropped, form-fitting style. Pair this bustier with a velvet mini skirt and rhinestone earrings.
Fit & Features
- Rhinestone thin shoulder straps
- Sweetheart neckline with rhinestone trim
- Padded cups with underwire
- Back zipper and hook and eye closure
- Front boning detailing to provide structure
- Cropped, form-hugging fit
- Satin-like fabric with minimal stretch
Style Number/Barcode: 06003-1061
Category Name: Night Out
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Twist Front Brushed Knit Crop Top
Elevate your everyday basic style with this trendy detailed crop top! It features long fitted sleeves, a V neckline, a twist front detail with cut-outs and a drawstring, and a cropped, form-hugging fit. The brushed knit fabric offers plenty of stretch for comfortable wear. Complete your outfit with mom jeans and chunky sneakers for an effortless look.
Fit & Features
- Long fitted sleeves
- V neckline
- Twist front detail with cut-outs and a drawstring
- Cropped
- Form-fitting style
- Brushed knit fabric
- Plenty of stretch
Style Number/Barcode: 06001-2989
Category Name: Night Out
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sparks Fly Velvet Sequin Mini Skirt
Let the sparks fly in this enchanting sequin mini skirt! It features an elasticized waist, bodycon fit, and a velvet-lined knit fabric with a moderate stretch. Complete the look in the matching top.
Shop The Matching Top: Sparks Fly Velvet Sequin Crop Top
Fit & Features
- Elasticized waist
- Bodycon fit
- Mini-length hem
- Sequin-velvet lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06401-0349
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chain My Mind Side Slit Midi Dress
This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.
Fit & Features
- Sleeveless square neck
- Chain link adjustable spaghetti straps
- Bodycon silhouette
- Side slit
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4800
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Schedule Full Oversized Square Sunglasses
An essential pair of oversized square sunglasses to slip on when you're on the go!
Fit & Features
- Oversized design
- Square shape
- Tinted lenses
- Chain link detail on arms
Style Number/Barcode: 07008-1129
Category Name: Night Out
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic And Sheer Lace Long Sleeve Top
Chic and sheer, this lace long sleeve top will bring the trendy allure. Designed with a textured sheer lace fabric, it features a crew neckline, long fitted sleeves with flared hems, and a fitted mid-length hem. Style over a basic bralette with high waist pants and mules!
Fit & Features
- Crew neckline
- Long fitted sleeves, flared hems
- Fitted mid-length hem
- Textured sheer lace fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-5071
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Illusion Contrast Mesh Bodysuit
This chic mesh bodysuit is designed to create the illusion of a sheer style with a contouring effect. Featuring a sleeveless sweetheart neckline, adjustable spaghetti straps, molded cups with a structured underwire, a striped contrast mesh bodice, and a thong bottom with a form-hugging fit. Complete the look in a polished matching blazer and trouser pants for dinner and drinks with the ladies!
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Molded cups, structured underwire
- Striped contrast mesh bodice
- Thong bottom, dual snap button closure, form-hugging fit
- Partial sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4583
Category Name: Night Out
Price: $3.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Art Display Strapless Bustier
Display an artsy vibe in this strapless bustier perfect for a gala opening downtown! It features flexible boning inserts for a structure, and a mid-length fitted hem, and is composed of a multi-printed mesh-lined fabric with a moderate stretch. Complete the look with flare pants.
Fit & Features
- Strapless bodice
- Flexible boning inserts
- Mid-length fitted hem
- Back zipper and hook-eye closure
- Multi-printed, lined mesh fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4769
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Impressions Six-Pack Ring Set
Make a glam impression accessorizing with this ring set featuring six styles each with various designs, colored stones, and rhinestone accents. Complete the look in chic earrings.
Fit & Features
- Six-pack ring set
- Various design
- Colored stones
- Rhinestone accents
Style Number/Barcode: 07004-0306
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bust Out The Rhinestone Satin Bustier
You deserve to sparkle! Bust out this satin bustier to instantly dress up your look. It features a sleeveless pleated cowl neckline, rhinestone embellished spaghetti straps with adjustable accents, an underbust seam, flexible boning inserts, and a crop-fitted hem. Style with high-rise flare pants for dinner and drinks with the ladies!
Fit & Features
- Sleeveless pleated cowl neckline
- Rhinestone embellished spaghetti straps, adjustable accents
- Underbust seam, flexible boning
- Cropped hem
- Hidden side zipper closure
- Silky satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4936
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pearl Ambition Sleeveless Bodysuit
Go for glam in pearl! The bodysuit features a sleeveless bodice, a mock neck and a thong bottom with snap button. The all over pearl and beaded accents are set in a baroque-inspired pattern. Bodysuit is composed of a sheer unlined mesh fabric hat offers a form hugging fit with a moderate stretch. Includes a thong bottom with snap button closure.
Style Number/Barcode: 06001-1329
Category Name: Night Out
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring The Heat One Shoulder Bodysuit
Bring the heat with this night out worthy bodysuit! It features a one shoulder neckline with a single long fitted sleeve and a thong bottom with dual snap button closures. The top of the bodysuit is composed of a sheer mesh adorned with all over heat stones, and the bottom is composed of a stretchy knit fabric. Includes a partial knit lining.Style Number/Barcode: 06001-1878
Category Name: Night Out
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Moment For Mesh Ruched Crop Top
Create a head-turning moment in a mesh crop top that commands attention! The top features a sweetheart neckline with a ruched drawstring, long sheer sleeves, and a cropped hem. Complete look with the matching midi skirt and mules.
Shop Matching Midi Skirt: Moment For Mesh Ruched Midi Skirt
Fit & Features
- Sweetheart neckline
- Ruched drawstring at the center
- Long sheer sleeves
- Cropped hem
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3576
Category Name: Night Out
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classy Chic Off-The-Shoulder Corset
Keep it classy with a cute corset that takes you from day to night! The corset features an off-the-shoulder neckline, a sweetheart bust, cold shoulder straps, contrast piping at the bodice, and hook and eye closures at the back. Complete look with high waist jeans and mules.
Fit & Features
- Off-the-shoulder neckline
- Sweetheart bust, chiffon cold shoulder straps
- Contrast piping, flexible boning
- Hook and eye closures at the back
- Cropped hem, form-hugging fit
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1353
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Strapless Satin Corset
Sleek and strapless, this satin corset top is a must-have for elevating casual outfits! It features a square neckline with an angled design, flexible boning, back hook and eye closures, and a cropped, form-hugging fit. Style this corset with your fave pair of jeans and clear heels.
Fit & Features
- Strapless square neckline, angled design
- Flexible boning
- Back hook and eye closures
- Cropped, form-hugging fit
- Smooth satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1509
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mesmerizing Shine Cubic Zirconia Teardrop Earrings
Mesmerize with earrings that radiate luxe shine for your special occasion outfit! The earrings feature a slim linear bar on post composed of mini rhinestones, a double-row of tear-drop-shaped cubic zirconia stones, and a post-back closure. Complete look with a formal satin dress and rhinestone heels.
Fit & Features
- Slim linear bar on post
- Mini rhinestones
- Tear-drop shape
- Cubic zirconia stones
- Pps-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0946
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab Steps Pointed Toe Sock Booties
Step out in these fab sock booties on your coffee run or going into the office! They feature a pointed toe, block heel, and a knit compression ankle. Style with trousers.
Fit & Features
- Pointed toe
- Block heel
- Knit compression ankle
- Faux suede
- Runs true to size
Style Number/Barcode: 07403-1330
Category Name: Night Out
Price: $12.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wow Factor Glitter Chain Strap Dress
Amp up the wow factor in this iridescent glitter mini dress for your next club night! The dress features a sleeveless square neckline with chain straps and a bodycon silhouette. Complete your sultry look in glitzy earrings.
Fit & Features
- Sleeveless square neckline
- Chain straps
- Bodycon silhouette
- Mini-length hem
- Sheer iridescent glitter knit fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05103-4661
Category Name: Night Out
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meant To Be Satin Lace Up Corset Top
This satin corset top is meant to be in your closet perfect for bringing romance to date nights or to dress up your favorite bottoms! It features a sleeveless square neckline, wide shoulder straps, a hidden front hook and eye closures, a cropped hem, and a customizable lace-up back. The top is composed of a lined satin woven fabric with minimal stretch. Complete the look in high-rise pants and heels.
Fit & Features
- Sleeveless square neck
- Wide shoulder straps
- Hidden front hook and eye closures
- Cropped hem
- Lace-up customizable back
- Lined satin woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2176
Category Name: Night Out
Price: $8.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Alluring Flirt High-Rise Lace Mini Skort
Alluring and flirty! Unveil this lace mini skort for a romantic look on your next date. The high-rise waist and uneven mini-length hanky hem create a sultry silhouette, while the stretchy knit shorts lining provides comfort and coverage. Complete the look in a mesh bodysuit and strappy sandals for an unforgettable outfit!
Fit & Features
- Sheer textured lace fabric, stretchy knit shorts lining
- High-rise waist
- Mini-length hanky hem
- A-line fit
- Runs true to size
Style Number/Barcode: 06503-1133
Category Name: Night Out
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dance The Night Away Sequin Mini Skirt
Dance the night away in this sequin mini skirt flaunting a high-rise waist and form-hugging fit. Complete the look with a crop top and heels.
Fit & Features
- Sheer knit fabric with stretchy knit lining
- All-over small and large sequin embroidery
- High-rise waist
- Side zipper with hook-eye closure
- Form-hugging fit
- Mini-length hem
- Runs large; recommend sizing down.
Style Number/Barcode: 06401-0722
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Call Me Baby Peep Toe Stiletto Booties
You'll have everyone calling you baby in this sexy pair! Designed with an ankle fit, a peep toe, a stiletto heel and a zipper closure. Composed of a faux suede. Pairs well with all outfits of course!Style Number/Barcode: 07403-0150
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance