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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Audrina Formal Sequin Midi Dress
Special Occasion
Come through with head-turning shine as you shimmy the night away in our sequined Audrina midi dress!
Fit & Features
- High Round Neckline
- Cap Sleeves
- Draped Cowl Back
- High Side Slit
- Sequins
- Lined Mesh | Minimal Stretch
- Side Zipper Closure
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0261
Category Name: Night Out
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Test Me Faux Leather Heeled Mules
Trust me, they wont test you in these mules! Designed with an almond toe, a single band atop, and another band mid foot. Mules feature an open back which makes them easy to slide on, and a high block heel. Composed of a faux leather material.Style Number/Barcode: 07401-0519
Category Name: Night Out
Price: $21.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lace Caged Top Romper
Sultry and stunning, this lace caged top romper was made for a girl's night out!
Fit & Features
- High neckline
- Back zipper | Hook and eye closure
- Cap sleeves
- Sheer lace top with caged detailing
- High waist
- Flowy knit shorts | Moderate stretch
Style Number/Barcode: 06503-0073
Category Name: Night Out
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getting My Way Coated Mini Skirt
Get things to go your way when you step out in the perfect outfit! No one will be able to say no to you gurl. Don't forget to pick up the matching top though....it only works if u got the whole 'fit
Shop Matching Top: Getting My Way Coated Cropped Top
Fit & Features
- High waist fit
- Elastic waist band | Stretch waist
- Form fitting silhouette
- Moderate stretch
- Mini hemline
- Smooth coated finish
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06501-0184
Category Name: Night Out
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Nice To Meet Ya Ruched Off Shoulder Mini Dress
Slip into a magical mini dress that will have them all dyin' to meet ya. Flattering ruched arms, and molded cups, give for a flirty fit!
Fit & Features
- Off shoulder neckline
- Long sheer sleeves
- Form fitting silhouette
- Molded cup at the bust
- Mini hemline
- Zipper center back
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05103-0813
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seraphina Formal Pearl Mini Dress
Special Occasion
Bring the luxe and shine like the rare pearl you are in our dazzling Seraphina dress! Pair her unmatched beauty with slingback stilettos and a glitzy clutch to complete your evening look!
Fit & Features
- Plunging V-Neckline | Mesh Inset
- Tank-Like Straps
- Pearl and Heat Stone Embellishments
- Mini Skirt Length Silhouette
- Lined Smooth Knit Fabric
- Form Hugging Fit | Slight Stretch
- Hidden Back Zipper Closure
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0408
Category Name: Night Out
Price: $19.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring the Flair Crepe Ruffled Dress
Bring the flair in this ruffled dress for your next night out! The dress features a plunging V-neckline and a ruffled asymmetrical hem. The dress is composed of a form-hugging crepe fabric that embraces curves while providing a retention stretch. Complete your look with sleek heels and rhinestone earrings.
Fit & Features
- Plunging V-neckline
- Sleek spaghetti straps
- Ruffled asymmetrical hem
- Crepe fabric
- Form hugging fit, moderate stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0823
Category Name: Night Out
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Faux Leather Biker Shorts
Glam up your biker shorts with sleek faux leather. Dress up your biker shorts with a ribbed button-down top and sleek stilettos for a night out. The shorts feature a high rise waist, a mid-thigh length, and composed of faux leather fabric.
Fit & Features
- High rise waist
- Mid-thigh length
- Faux leather fabric
- Form hugging fit
Style Number/Barcode: 06503-0189
Category Name: Night Out
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Glow Up Strappy Stiletto Heels
Glow up in these gorgeous and sleek strappy stiletto heels! They feature a trendy pointed toe and a strappy design with a metallic finish. Pair these heels with a little black dress for a chic night out.
Fit & Features
- Pointed toe
- Strappy design
- Adjustable around the ankle strap
- Stiletto heels
- Patent PU material
Style Number/Barcode: 07401-2430
Category Name: Night Out
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry And Stunning Cowl Neck Crop Top
Create a stunning look for a night out in this sultry crop top! It features bungee spaghetti straps that lead to a back gold metal O-ring accent, an open strappy back design, a cowl neckline, and a cropped, form-hugging fit. Complete your outfit with faux leather pants and heels.
Fit & Features
- Bungee spaghetti straps
- Back gold metal O-ring detail
- Open strappy back design
- Cowl neckline
- Cropped, form-fitting style
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-3455
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry And Sassy Snake Print Bodysuit
Sultry and sassy will be your vibe in this on-trend snake print bodysuit. It features a sleeveless deep V-neckline with a wrap-front design, spaghetti straps, ruched detailing, and a contrasting knit bottom. Complete the look with a faux leather mini skirt and ankle booties.
Fit & Features
- Sleeveless V-neckline, wrap-front design
- Spaghetti straps
- Ruching
- Knit top with snake print design, contrasting knit thong bottom
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-3266
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic And Mod Patent Faux Leather Booties
You'll look oh-so-chic in these mod patent faux leather booties! They feature a trendy square toe, an above the ankle design, an inner zipper closure, and a block heel. Style these booties with a basic bodysuit and a cute plaid mini skirt.
Fit & Features
- Square toe
- Above the ankle design
- Inner zipper closure
- Block heel
- Patent faux leather material
- Runs true to size
Style Number/Barcode: 07403-1351
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek And Fab Satin Crop Top
Keep it sleek and stylish with a crop top that brings major luxe! The top features a sleeveless cowl neckline, adjustable spaghetti straps, flexible boning at the back, a hook and eye back closure, and a cropped hem. The top is composed of a satin fabric that offers a relaxed fit with minimal stretch. Complete look with high waist pants and heels.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Flexible boning at back
- Hook and eye closure at back
- Cropped hem
- Satin fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06003-1461
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirtatious Fashionista Crop Top
Showcase your flirtatious fashionista side in this fitted crop top! It features a trendy one-shoulder neckline, a single long sleeve, and a cropped, form-hugging fit. Style this top with the matching maxi skirt and clear heels for a night out with the girls!
Shop Matching Bottoms: Flirtatious Fashionista Maxi Skirt
Fit & Features
- One-shoulder neckline
- Single long fitted sleeve
- Cropped, form-hugging fit
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06001-3829
Category Name: Night Out
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Fling Cap Sleeve Corset Bodysuit
You'll surely fall for this sultry lace bodysuit perfect for cocktail hour! It features peasant cap sleeves, a sweetheart neck with built-in bust support, a corset bodice with hook-eye closures, and flexible boning. Composed of a sheer mesh lace fabric with minimal stretch. Style with distressed jeans and stiletto heels.
Fit & Features
- Peasant cap sleeves
- Sweetheart neck, built-in bust support
- Corset bodice, hook-eye closures, flexible boning
- Sheer mesh lace fabric, minimal stretch
- Thong-cut bottom, dual snap closure
- Fits true to size
Style Number/Barcode: 06003-1580
Category Name: Night Out
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet But Spicy Halter Cutout Ruffle Skater Dress
So flattering for a night-out occasion, this skater dress is featured in a flattering halter neckline with a chic hoop insert and a cutout bodice that shows some skin!
Fit & Features
- Mesh-lined fabric
- Halter neckline, spaghetti strap tie, hoop insert
- Cutout bodice
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000011
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Fling Twist Slit Maxi Skirt
So much for a summer fling! With this maxi skirt, you're sure to fall for it over and over again. It features a high-rise waist with a twist accent, a front high-cut slit, and a form-fitting silhouette on lined knit fabric. Complete your look with the matching top.
Shop Matching Top: Summer Fling Twist Front Crop Top
Fit & Features
- High-rise waist with twist accent
- Front high-cut slit
- Form-fitting silhouette
- Maxi-length hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0673
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Well Played Denim Bodycon Wrap Midi Dress
Well played! This denim midi dress is the perfect pick for having all eyes on you. It features a square neckline, adjustable straps, and a side pleated seam that creates the bodycon silhouette with an asymmetrical wrap slit hem. Complete the look in cute stiletto mules for a day or night out!
Fit & Features
- Sleeveless square neckline, adjustable straps
- Back zipper and hook-eye closures
- Side pleated seam
- Bodycon silhouette, asymmetrical wrap slit
- Midi-length hem
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5251
Category Name: Night Out
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Design High Rise Lace Faux Leather Mini Skirt
This faux leather mini skirt with a gorgeous lace trim hem adds a touch of femininity. The flattering high-rise waist and bodycon silhouette finish the look.
Fit & Features
- Faux leather material, woven lining with lace trim
- High rise waist
- Back zipper and hook-eye closure
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0658
Category Name: Night Out
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Baddie Strapless Cutout Woven Crop Top
Let this cutout crop top show off what a major baddie you are! Designed with a structured woven fabric, this crop top features a strapless sweetheart neckline with a center V-wired design to accentuate your bust, and asymmetric seams leading to small side cutouts for a hint of skin. The cropped hem and form-hugging fit will give you that snatched silhouette. Style with the matching maxi skirt and sleek stiletto heels!
Shop Matching Bottoms: Major Baddie High Waist Belted Woven Maxi Skirt
Fit & Features
- Non-stretch woven fabric with lining
- Strapless sweetheart neckline with V-wired design, no-slip strip
- Asymmetric seams and side cutouts
- Back zipper with hook and eye closure
- Cropped hem
- Fitted
- Runs true to size
Style Number/Barcode: 06003-2449
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flourish In Style Floral Applique Satin Crop Top
Flourish with undeniable style in this satin crop top adorned with floral applique perfect for showing off on an evening out! The sweetheart neckline and padded bust add shape and support, while the adjustable spaghetti straps with floral applique give a touch of uniqueness. The multiple back hook and eye fasteners ensure a secure fit. Complete the look in a sleek mini skirt and heels.
Fit & Features
- Satin woven fabric, no stretch
- Adjustable spaghetti straps, floral applique
- Sweetheart neckline with floral applique
- Multiple back hook and eye fasteners
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2337
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitzy Era Ruffled Slit Ruched Glitter Midi Dress
This stunning ruffled slit ruched glitter midi dress will have you in your glitzy era! Designed with a stretchy lined glitter knit fabric, this mid-length dress features a sleeveless V-neckline, spaghetti straps, a ruched side seam to accentuate your gorgeous curves, and an asymmetric ruffled hem creating a stylish side slit on the bodycon silhouette. Complete your dressy party look with rhinestone heels!
Fit & Features
- Stretchy lined glitter knit fabric
- Sleeveless V-neckline, dart seams
- Spaghetti straps
- High waist seam, ruched side seam
- Asymmetric ruffled hem, side slit
- Bodycon fit
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-2964
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always On Trend Off-The-Shoulder Abstract Mini Dress
Always on trend, this off-the-shoulder dress features fitted long sleeves and flattering side ruched seams that flaunt your figure along the bodycon mini-length silhouette. Perfect for styling with heels for a night out.
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining, moderate stretch
- Off-the-shoulder folded neckline
- Fitted long sleeves
- Side ruched seams
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-5626
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Baddie Thong Back Ruched Dress
You'll look like a total baddie when you slip into this ultra-flattering ruched dress! It features thin spaghetti straps, a square neckline, and a low-cut back with a thong cutout. We guarantee you'll have everyone stopping to stare when you wear it with sparkling heels and a clutch.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Low-cut back with thong detail, ruching
- Mini-length silhouette
- Form-hugging fit
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3916
Category Name: Night Out
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale