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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Stylish And Studded Face Mask
Stay safe while also showcasing a chic and stylish look in this studded face mask! It features all over studded detailing with earloops for a comfortable fit. Pair with a sleek little black dress for a gorgeous vibe.
Fit & Features
- All over studded detailing
- Earloops
- Wash before and after use is recommended
- Not a medical-grade mask
- Final Sale
Style Number/Barcode: 07305-0142
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Trendsetter Heeled Sandals
You'll be the trendsetter amongst your squad in these adorable heeled sandals! They feature an of the moment square toe, a slide-on design, and a sturdy little stiletto heel. Pair these chic sandals with denim and a crop top for the perf everyday 'fit.
Fit & Features
- Square toe
- Thong sandal design
- Puffy-like straps
- Small stiletto heel
- PU material
Style Number/Barcode: 07401-2465
Category Name: Night Out
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Chic Chain Link Mask Chain
Dazzle with a mask chain to keep your face mask or sunglasses close by, girl! The chain features a trendy chain-link design and lobster clasp closures. Complete your look with a chic face mask.
Fit & Features
- Trendy chain-link design
- Lobster clasp closures
- Can be attached to use on a face mask or sunglasses
Style Number/Barcode: 07308-0149
Category Name: Night Out
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Trendy chain-link design
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Edgy-Chic Coated Faux Leather Mini Skirt
Edgy and oh-so-chic, this coated faux leather mini skirt is perf for a GNO. It features a flattering high rise waist and a trendy envelope design with an overall form-hugging silhouette. Simply add on some trendy heels for a gorgeous look.
Fit & Features
- High rise waist
- Curve-hugging fit
- Envelope front design
- Asymmetrical hem
- Coated faux leather fabric
Style Number/Barcode: 06401-0265
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Satin Faux Wrap Mini Skirt
Sleek and sassy, this satin faux wrap mini skirt is the must-have satin piece you need this season! It features a flattering high rise waist and a flowy A-line fit with a slightly flared hem. Pair this skirt with a statement crop top for a gorgeous fall vibe.
Fit & Features
- High rise waist
- Faux wrap front with tie at waist
- A-line fit
- Satin woven fabric
Style Number/Barcode: 06401-0266
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Luxe Cropped Velvet Tank
Lounge in a luxe velvet cropped tank that brings the glam! The tank features a plunging V-neckline, adjustable spaghetti straps, padded cups, and a cropped hem. The tank is composed of a ribbed velvet fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching joggers.
Shop Matching Joggers: So Luxe High Rise Velvet Joggers
Fit & Features
- Sleeveless V-neckline
- Padded cups
- Adjustable spaghetti straps
- Cropped hem
- Ribbed velvet fabric
- Form hugging fit, moderate stretch
- Matching joggers sold separately
Style Number/Barcode: 06001-2952
Category Name: Night Out
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Moment In Plaid High Waist Mini Skirt
Create a fab moment in a plaid skirt that wows! The skirt features a high rise waist, a plaid print, and a mini side slit. Complete look with a crop top and thigh high boots.
Fit & Features
- High rise waist
- Plaid print
- Mini side slit
- Mini length silhouette
Style Number/Barcode: 06501-0322
Category Name: Night Out
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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See Me Now Lucite Block Heels
Get seen and noticed in chic heels that command attention. The heels feature an adjustable ankle strap, an open almond toe with a clear strap over the toe, and a lucite block heel. Complete look with a sweater dress for a casual date night.
Fit & Features
- Open-back
- Adjustable ankle strap
- Open almond toe
- Clear strap over the toe
- Lucite heel
Style Number/Barcode: 07401-2461
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Fab Wrap-Around Block Heels
You'll look oh so fab in these stylish wrap-around block heels! They feature a chic design with a cute tie back closure and a sturdy block heel. Pair these with a curve-hugging pencil skirt to elevate your workwear look.
Fit & Features
- Open almond toe
- Wrap-around design
- Tie back closure
- Closed ankle
- Block heel
- Faux suede fabric
Style Number/Barcode: 07401-2463
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Penny Formal Woven Glitter Asymmetrical Mini Dress
Special Occasion
Dazzle and glow in our shimmery Penny dress that brings that megawatt shine to your special evening. She features a wrap V-neckline, adjustable spaghetti straps, and a mini length silhouette with an asymmetrical hem. She is composed of woven glitter knit fabric that offers a form hugging fit with a moderate stretch. Complete your formal evening outfit with rhinestone earrings and a dainty rhinestone bracelet.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Mini length silhouette
- Asymmetrical hem
- Woven glitter fabric
- Form hugging fit
- Moderate stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0470
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Belted Faux Leather Paper Bag Mini Skirt
Get a chic, edgy vibe in this trendy belted faux leather mini skirt! It features a flattering paper bag waist and a curve-hugging fit. Pair this skirt with a cute sweater and thigh-high boots for a go-to fall night out look.
Fit & Features
- High rise paper bag waist
- Included belt
- Short, form-hugging fit
- PU fabric
Style Number/Barcode: 06401-0262
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunning And Sultry Sweetheart Mini Dress
Create a stunning and sultry look in this gorgeous sweetheart mini dress! It features a sleeveless bodice with spaghetti straps, a mini length silhouette and a curve-hugging fit. Pair this dress with a faux leather jacket for a girl's night out.
Fit & Features
- Spaghetti straps
- Sweetheart neckline with seam detailing at the bust
- V back
- Short, form-hugging fit
- Ribbed knit fabric with plenty of stretch
Style Number/Barcode: 05102-1039
Category Name: Night Out
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classy Chic Faux Suede Peep Toe Mules
Keep it classy in chic mules to dress up your workwear outfits! The mules feature an open back, a wide strap over the toe, a peep toe, and a block heel. Complete look with a blouse and pencil skirt.
Fit & Features
- Open back
- Wide strap over the toe
- Peep toe
- Block heel
- Faux suede material
Please be advised that these mules run a 1/2 size too small.
Style Number/Barcode: 07401-2459
Category Name: Night Out
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instant Classic Peep Toe Stilettos
Create an instant classic moment in heels that bring all the style for your outfits! Perfect for creating chic workwear outfits, that take you to happy hour, these heels are a must. The heels feature a faux patent leather body, a peep toe, and a stiletto heel. Complete look with a ribbed midi dress and blazer.
Fit & Features
- Peep toe
- Faux patent leather body
- Stiletto heel
- Closed-back
Please be advised that these heels run 1/2 a size small.Style Number/Barcode: 07401-2460
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stay Stylish Over The Knee Boots
Keep it stylish and chic in these fab over the knee boots! They feature a flattering almond toe, a sturdy block heel, and a tie back detail. Pair these boots with a plaid mini skirt for a holiday party.
Fit & Features
- Over the knee design
- Almond toe
- Block heel
- Tie back detail
- Faux suede material
Please be advised that these boots run a 1/2 size too small.
Style Number/Barcode: 07402-0224
Category Name: Night Out
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched To The Maxi Knit Dress
This sultry long summer-ready dress is ruched to the max! It features a sleeveless bodice, spaghetti straps, a square neck and back, a front and back waist cutout, ruched detailing along the sides, and a floor-length hem with a knee-high side slit. The dress is composed of a stretchy knit with a short knit skirt lining and offers a flattering, curve-hugging fit. Complete your look with wedges and statement earrings.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Front and back cutouts
- Ruched dealing
- Maxi length silhouette
- Knee-high slit
- Form hugging fit, stretchy knit fabric
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0886
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Faux Leather Hot Shorts
Get cheeky in these faux leather hot shorts for a sleek and flirty look. Step out in style in these high-waist shorts designed with a wide waistband perfect to wear with a bodycon bodysuit or crop bustier top. The faux leather material instantly makes shorts the perfect bottoms to pair with your going-out looks for a girls' night out or clubbing.
Fit & Features
- High-rise waist
- Thick waistband
- Cheeky fit
- Faux leather fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0150
Category Name: Night Out
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Statement Collar Necklace and Stud Set
Make a statement with a collar necklace that brings the drama! The set features an extra-large curved metal collar and matching stud earrings. Style with a LBD for a stunning date night outfit.
Fit & Features
- Extra-large collar with a curved design
- Matching stud earrings
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07002-0569
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Bling Door Knocker Earrings
You'll for sure bring the bling in these fab door knocker earrings! They feature a round post with a rectangular door knocker design and an overall textured finish. Pair these statement earrings with a faux fur coat for a major fashionista look.
Fit & Features
- Round post
- Rectangular door knocker design
- Textured detailing
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0694
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Snake Print Face Mask
Stay safe while making a sassy statement in this adorable face mask! It features an allover snake print and earloops for comfortable wear. Pair this face mask with your basic everyday 'fit to give it a trendy vibe.
Fit & Features
- Allover snake print
- Earloops
- This is not a medical-grade mask nor is a substitute for medical-grade equipment
- Wash before and after use is recommended
- Please consult local health authority for guidance on the use of non-medical grade masks
Face masks are final sale merchandise and may not be returned or exchanged.
Style Number/Barcode: 07305-0206
Category Name: Night Out
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pleated Skater Mini Skirt
Bring the flair with a pleated mini skirt! The skater skirt styles perfectly with your crop tops for a casually cute look! The skirt features a high rise waist and a pleated skater silhouette.
Fit & Features
- High rise waist
- Pleated
- Skater silhouette
- Mini length
Style Number/Barcode: 06501-0320
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Light The Night Rhinestone Fringe Sphere Clutch
Let this sphere clutch light up your night to add that special detail to your formal evening outfit. The clutch features a one-of-a-kind sphere shape, a cascading fringe design throughout and a rhinestone embellished O-ring handle. Complete your glitzy look with a velvet dress and rhinestone cuff.
Fit & Features
- Sphere-shaped body
- Cascading rhinestone fringe design
- Rhinestone embellished O-ring handle
Style Number/Barcode: 07204-0164
Category Name: Night Out
Price: $17.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stunner Snake Print Mini Skirt
You'll be the stylish stunner of your squad in this trendy mini skirt! It features a high rise elastic banded waist, ruched detailing, and a short, curve-hugging fit. The skirt is composed of a brushed knit fabric with plenty of stretch and has an all-over snake print. Pair it with strappy heels and a faux leather jacket.
Fit & Features
- High rise elastic banded waist
- Ruched detailing
- Short, form-hugging fit
- Brushed knit fabric
- Plenty of stretch
- Snake print
Style Number/Barcode: 06501-0318
Category Name: Night Out
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale