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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Ponte In Your Direction Blazer
Lead the way in this chic blazer. It features a notch collar and open front, slight shoulder padding, three-quarter sleeves with a snap button detail and accent pockets. Ponte fabric offers minimal stretch.
Style Number/Barcode: 06204-0115
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Zipped Jacket
It's all in the zipper details! This moto jacket is a must for a chic and sleek vibe. Layer this jacket for a night out with the squad. The jacket features an asymmetrical zipper front, small zippered pockets, zipper details on the shoulder, a cropped, form-hugging fit, and is composed of faux leather fabric. Complete your look with high waist denim jeans and sleek hoops.
Fit & Features
- Asymmetrical zip front
- Zipper details along the shoulders
- Small zipper pockets
- Cropped silhouette, form-hugging fit
- Faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-3077
Category Name: Night Out
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Biker Chic Crop Jacket
Change gears in a cropped jacket and add a little biker chic-ness to your look! Create an edgy look in this biker moto jacket that features an asymmetrical zipper front with a lapel collar, snap button accents, and an adjustable waist belt.
Fit & Features
- Faux leather fabric with no stretch, smooth lining
- Lapel collar, asymmetrical zippered front
- Long sleeves with zippered accents
- Zipper and snap button accents
- Adjustable waist belt
- Runs true to size
Style Number/Barcode: 06204-2669
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Faux leather fabric with no stretch, smooth lining
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Making The Rules Boyfriend Blazer
Take charge and make your own rules in this statement blazer!
Fit & Features
- Flat collar
- Slight shoulder padding
- Long roll up sleeves
- Two faux front pockets
- Oversized boyfriend fit | Drape open front
- Lined textured woven fabric
- Relaxed fit | Minimal stretch
Ivory: Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0114
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Baddie Babe Moto Jacket
You're just a baddie with a chic sense of style! This black moto jacket features an asymmetrical zipper front, long sleeves, a zippered pocket, an adjustable belted hem and rose gold hued metal accents. Moto is composed of a lined faux leather fabric that offers a form hugging fit with a slight stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06204-0049
Category Name: Night Out
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux In Love With Suede Jacket
Fall in love with this chic and sleek faux suede moto jacket! It features a collar with silver faux button details, buttoned shoulders, long sleeves with zipper accents, an asymmetrical zip front, zippered pockets on the front, and a belted waist with a silver buckle and grommets. The black jacket is composed of a smooth faux suede fabric with a woven lining.Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.
Style Number/Barcode: 06204-0011
Category Name: Night Out
Price: $15.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Laced In Elegance Cardigan
Keep it poised and elegant in lace! This black cardigan features a V neckline, a multi button down front, long sleeves and a cropped hem. Cardigan is composed of an unlined floral lace fabric that offers a relaxed fit with minimal stretch.
Style Number/Barcode: 06202-1128
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Caught In A Mesh Top
Get caught up in this hot mesh of a top! This black, crop top has a flattering V neckline paired with a tie front, knot closure and long, narrow sleeves. The crop top is composed of a sheer, unlined mesh that offers plenty of stretch.Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.
Style Number/Barcode: 06202-1098
Category Name: Night Out
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Show Em' Who's Boss Bomber
Show em' who's boss in this commanding camo bomber! The jacket features a drawstring hood, long sleeves with cinched cuffs, a complete zip front, front pockets, and an elastic banded hem. Pair this trendy jacket with a basic crop top and biker shorts for a casual-chic look.
Fit & Features
- Drawstring hood
- Long sleeves
- Zip front
- Front pockets
- Elastic banded hem
- Sheer mesh fabric with moderate stretch
- Mesh and nylon hood and partial nylon back
Style Number/Barcode: 06202-1087
Category Name: Night Out
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut To The Chase Bandage Dress
Let's cut to the chase - this little black dress couldn't get any sultrier! It features a sleeveless bodice, spaghetti straps, a square neckline, bold and sexy side cut outs with bar accents, and an exposed back gold zipper and hook and eye closure. The dress is composed of a bandage knit fabric that offers a curve hugging fit and plenty of stretch.
Style Number/Barcode: 06005-6240
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Social Butterfly Lace Crop Top
Show off that charisma in this adorable white crop top! It features an all over lace with lined cups, a deep V neckline with hook and eye closures, scalloped trim and adjustable straps.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9876
Category Name: Night Out
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ravishing Lace Bodysuit
Nothing says ravishing like risque lace! The sleeveless bodysuit has an underwire bust paired with adjustable, elastic straps and a scoop back that features an additional strap detail. The cheeky bodysuit is composed of a sheer, unlined lace and mesh fabric, detailed with black piping and closes with a hook and eye bottom.Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 06003-9890
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortlessly Embellished Crop Top
Create an effortless look with beyond gorg embellishments in this sheer mesh crop top! It features a crew neckline, short sleeves, and a cropped hem. The black top is adorned with pretty pearls and rhinestones. Top offers moderate stretch. Undergarment not included.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-9888
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Beauty Lace Bustier
Draw all eyes on you as you dazzle in this statement making bustier! It features a sweetheart bust, unlined cups with underwire, adjustable narrow straps and a wired V inset. Bustier is composed of an unlined sheer floral lace fabric adorned with mini rhinestones throughout. Garment offers a form hugging fit with minimal stretch and includes a multi row fish hook closure.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9867
Category Name: Night Out
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
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Sweet Stuff Banded Crop Top
A little sweet, a little naughty. This black crop top features a daring strapless sweetheart neckline, a back zipper and a band hemline. Top is composed of a knit fabric with moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9877
Category Name: Night Out
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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For The Record Sleeveless Crop Top
Set the record straight with this daring crop top! The tank has wide shoulder straps paired with an exposed zipper front and underbust seams.The crop top is composed of a smooth, Vinyl fabric that offers a moderate stretch.
Style Number/Barcode: 06003-9831
Category Name: Night Out
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tied With Class Satin Bodysuit
Get tied up in this classy top! The bodysuit has notched, lapel collar paired with a tie front waist and long, button cuff sleeves. The bodysuit is composed of a smooth satin and includes a thong bottom with a snap button closure.
Style Number/Barcode: 06003-9827
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Fine In Rhine Bustier Top
Slay a flawless look in sparkling rhinestones! This pink bustier top features uplifting molded cups, adjustable narrow straps, a cropped hemline and a multi row hook clasp closure. The all over pink rhinestones is all you need for a dazzling look!Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-9807
Category Name: Night Out
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhine And Shine Halter Top
Rise and shine with this fun rhinestone halter top! It features a sleeveless bodice, an open back, metal chain halter and bar straps with lobster clasp closures, a V neckline, and a cropped hem. The top is composed of a lined chain mail metal adorned with dazzling mini rhinestones.
Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-9782
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love In Lace Bustier
Fall in love with lace with this gorgeous bustier top! It features a sleeveless bodice, a flattering underwire, sweetheart bust, adjustable spaghetti straps, a back hook and eye closure, and a pretty eyelash trim detail. The black top is composed of a sheer lace fabric with a form-fitting style.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-9772
Category Name: Night Out
Price: $9.94 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Style Wrap Top
This flattering snake print top will always be in style! It features a wrap bodice that ties at the waist, long sleeves, and a relaxed fit throughout. Top is composed of a smooth knit fabric.
Style Number/Barcode: 06003-9757
Category Name: Night Out
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Festive Vibes Crop Top
Vibe with all those festival feels in this flirty crop top! It features a sleeveless bodice, a halter neckline with a tie back closure, an open back with a tie back, and a cropped hem. The black sheer mesh top has an embroidered floral pattern with a scalloped hem and no stretch.Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-9745
Category Name: Night Out
Price: $19.00 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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What An Angel Bustier Bodysuit
What's your secret for being sweet and sexy? This black bodysuit features a plunging sweetheart neckline, a lace bustier bodice with padding and underwire, long fitted sleeves, a hidden back zipper closure, and a knit bottom with snap button closures. Bodysuit is composed of a sheer mesh fabric.
Style Number/Barcode: 06003-9718
Category Name: Night Out
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Bubbly Chiffon Top
This plum chiffon top will have you feeling like a boss! It features a stretchy off the shoulder neckline, long sleeves with elastic cuffs, a bubble hem, and a contrasting back knit panel for added stretch. Top is composed of a chiffon fabric with a relaxed fit and minimal stretch and includes a lightly padded bust.Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-9669
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance