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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Sequin Stunner High Waist Joggers
You'll be a total stunner in these fabulous high waist sequin joggers! They feature a tie front detail and a relaxed yet chic fit. Pair these with a stylish boyfriend blazer to amp up your work from home look.
Fit & Features
- High waist
- Tie front
- Slanted front pockets
- Relaxed fit
- Jogger hem
- Allover sequin embroidery
- Woven fabric
Style Number/Barcode: 06402-0276
Category Name: Night Out
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Get Spotted Glitter Mesh Crop Top
Get spotted in this chic top that makes a glam statement! The top features a sheer unlined mesh fabric, a leopard spot design, and glitter embellishments throughout. Complete your night out look with a black mini skirt.
Fit & Features
- Crew neckline
- Sheer unlined mesh fabric
- Leopard spot design
- Long sleeves
- Glitter embellishment throughout
- Cropped hem
Style Number/Barcode: 06001-2844
Category Name: Night Out
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Child Snake Print Mesh Midi Skirt
Stay fierce in a midi skirt as wild as you! It features a high rise curve-hugging fit with a sultry side slit with ruched detailing. Pair this snake print mesh skirt with a basic bodysuit and heels for a girl's night.
Fit & Features
- High rise waist
- Mid-length, form-hugging fit
- Ruched detailing
- Side slit with tie detail
- Mesh fabric
- Allover snake print
Style Number/Barcode: 06501-0294
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Row Rhinestone Crawler Earring
Standout with a crawler stud to give your look a glam hint of edge. The stud features a traditional crawler design and a double-row of mini rhinestones. Complete your outfit with a fab matching set.
Fit & Features
- Long crawler design
- Double-row
- Rhinestones
- Post-back closure
- Single stud included
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-0672
Category Name: Night Out
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Waist Luxe Velvet Pants
Bring the luxe in high waist pants that are perfect for dressing up in! The pants feature a high rise waist, side pockets, and a straight leg fit. The pants are composed of a lined velvet fabric that offers a relaxed fit with a moderate stretch. Complete look with a crop top.
Fit & Features
- Elastic high rise waist
- Slant pockets
- Straight leg fit
- Lined velvet fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 06502-0413
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux Fur Long Line Jacket
Stun in a faux fur jacket to layer with all your chic style staples. The jacket features a collared neckline, long sleeves, a single button-down front, lined side pockets, and a long line length. The jacket is composed of a lined faux fur fabric that offers a relaxed fit with minimal stretch. Complete look with a trendy plaid mini dress and ankle booties.
Fit & Features
- Collared neckline
- Single button-down front
- Long sleeves
- Hidden side pockets
- Long-line length
- Lined faux fur fabric
Style Number/Barcode: 06201-0120
Category Name: Night Out
Price: $15.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Strappy Square Toe Platform Heels
Stylish and strappy, these platform heels are a trendy upgrade from your typical block heel. They feature an of the moment square toe, a wrap around the ankle strappy design, and a sturdy block heel. Pair these statement shoes with a simple mini dress and add some gold hoops to glam it up.
Fit & Features
- Square toe
- Thin clear toe strap
- Wrap around strappy design
- Tie back closure at ankle
- Open back
- Platform
- Block heel
Style Number/Barcode: 07401-2415
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Vibes Ruched Knit Catsuit
Get those major sultry vibes in this curve-hugging ruched catsuit, a perf alternative to the classic LBD. It features a sleeveless bodice with a sweetheart neckline and a ruched, form-hugging fit. Wear with some statement earrings and heeled mules for a gorgeous look.
Fit & Features
- Spaghetti straps
- Sweetheart neckline
- Form-hugging fit
- All over ruched detailing
- Knit fabric
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06502-0407
Category Name: Night Out
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Stunner Snake Print Tunic
Showcase stunning looks in this sleek satin snake print tunic! It features a collared neckline with a complete button-down front, cinched seam detailing under the bust, and a flowy, relaxed fit. Pair this tunic over a faux leather mini skirt for an edgy-chic vibe.
Fit & Features
- Collared neckline
- Complete button-down front
- Long sleeves
- Cinched seam detailing under bust
- Relaxed fit
- Allover snake print
- Satin fabric
Style Number/Barcode: 06003-1039
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Prowl Faux Fur Jacket
Strike a fierce layered look in a jacket that channels your inner fashionista. The jacket features a collared neckline, long sleeves, side pockets, and a trendy leopard print. The jacket features a faux fur fabric that offers a relaxed fit and includes a knit lining. Complete look with a bodysuit and liquid leggings.
Fit & Features
- Collared neckline
- Long sleeves
- Side pockets
- Leopard print
- Faux fur fabric with knit lining
- Relaxed fit
Style Number/Barcode: 06201-0121
Category Name: Night Out
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Striped Satin Joggers
Keep it sleek in joggers that make a stylish statement. The joggers feature a high-rise waist, a tuxedo-style stripe down the leg, and a skinny leg fit with a tapered hem. Complete your look with a black crop top.
Fit & Features
- High-rise waist, elastic band
- Tuxedo stripe
- Skinny leg fit, tapered hem
- Satin-like fabric, minimal stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06402-0274
Category Name: Night Out
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Clearly Stylish Lucite Block Heels
Clearly you'll have a stylish 'fit in these trendy block heels! They feature an open almond toe with a clear toe strap and a sturdy clear lucite block heel. Pair these shoes with a little black dress for a fun girl's night out.
Fit & Features
- Open almond toe
- Clear toe strap
- Clear adjustable around the ankle strap with buckle detail
- Open back
- Clear lucite block heel
- Patent PU material
Style Number/Barcode: 07401-2412
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Extra Faux Fur Stiletto Heel
Channel your inner diva in stilettos that are bold and command attention! The heels feature a faux fur ankle strap, an open almond toe, a faux fur strap over the toe, and a sleek stiletto heel. Complete your so extra look with a mesh crop top and a midi skirt.
Fit & Features
- Zippered back
- Faux fur ankle strap
- Open almond toe
- Faux fur strap over the toe
- Stiletto heel
Please be advised that these heels run 1/2 a size too small.
Style Number/Barcode: 07401-2403
Category Name: Night Out
Price: $14.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace Trim Knit Biker Shorts
Get on the biker short trend with this chic lace trim version! They feature a flattering high rise waist with a mid-thigh hem and pretty lace trim. Pair with a crop top and a tapered blazer for a cute happy hour look with the girls.
Fit & Features
- High rise waist
- Mid-thigh length
- Sheer lace trim
- Curve-hugging fit
- Knit fabric with a pretty sheen
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06503-0163
Category Name: Night Out
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring It Back To Basics Thin Block Heel
Slay in basic heels that go with everything with ease! Perfect for your next date night or bringing the chic factor to workwear outfits—these heels are a must baby girl! The heels feature an adjustable ankle strap, an open almond toe with a single strap over the toe, and a sleek thin block heel. Complete your look with a ribbed midi dress and blazer.
Fit & Features
- Adjustable ankle strap
- Open almond toe
- Single strap over the toe
- Thin block heel
Style Number/Barcode: 07401-2405
Category Name: Night Out
Price: $14.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kathy Iridescent Sequin Mini Dress
Special Occasion
Shine on in a sequin dress that brings the glitz and glam. Kathy features a plunging sleeveless V-neckline, iridescent sequins embroidered throughout, adjustable spaghetti straps for a customized fit, and a mini-length hem with a bodycon silhouette that will hug your curves. The sheer velvet fabric includes a full knit lining and offers a moderate stretch. Complete your A-list-worthy look with clear heels and rhinestone hoops.
Show off your style in this standout dress. Feeling the short and chic vibe? Discover more fashion-forward short prom dresses or elevate your style with our formal dresses.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Back zipper, hook and eye closure
- Mini-length hem, bodycon silhouette
- Iridescent sequin embroidery
- Sheer velvet fabric, full knit lining, moderate stretch
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05001-0493
Category Name: Night Out
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Karina Formal Sequin Cross-Back Mini Dress
Special Occasion
Stun in the Karina sequin mini dress that brings the shine to your special evening! She features a plunging V-neckline with a built-in padded bust for support, sparkling sequins set in a filigree design, and a sexy open back with sleek cross straps. The sheer mesh fabric includes a full-length knit lining and offers moderate stretch. Complete your formal evening outfit with sleek stilettos and earrings.
Fit & Features
- Plunge V-neckline, dual bungee spaghetti straps
- Built-in padded bust, no bra required
- Filigree sequin embroidered design
- Open back, sleek criss-cross straps
- Bodycon silhouette, mini-length hem
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05001-1151
Category Name: Night Out
Price: $14.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek and Strappy Stiletto Heels
Keep it sleek in these lace-up heels that impress! The heels feature lace-up straps, a square toe with a thong toe strap, and a sleek stiletto heel. Complete look with a ribbed knit midi dress to create a stunning night out look.
Fit & Features
- Lace-up straps
- Square toe with thong toe strap
- Adjustable ankle strap
- Square toe sole
- Sleek stiletto heel
- Faux leather material
Style Number/Barcode: 07401-2413
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow Up Cutie Thin Block Heel
Glow up in heels that bring the dazzle to your date night outfits. The heels feature an adjustable ankle strap, an open almond toe with a single strap over the toe, and a sleek thin block heel. Heels feature a dazzling metallic-like finish. Complete your look with a ribbed midi dress and blazer.
Fit & Features
- Adjustable ankle strap
- Open almond toe
- Single strap over the toe
- Thin block heel
- Metallic-like finish
Style Number/Barcode: 07401-2406
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Minimal Moment Thin Block Heels
Keep it minimal in heels that simply go with everything. Dress up your casual outfits with these fab heels. The heels feature an adjustable ankle strap, an open almond toe with a single strap over the toe, and a sleek thin block heel. Complete your look with a ribbed midi dress and blazer.
Fit & Features
- Adjustable ankle strap
- Open almond toe
- Single strap over the toe
- Thin block heel
Style Number/Barcode: 07401-2407
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Suede Platform Lace-Up Booties
Elevate your chic everyday style with these faux suede booties! They feature a chunky platform and an adorable lace-up back detail. Pair these booties with dark wash skinny jeans for an elongated look.
Fit & Features
- Ankle-high design
- Almond toe
- Inner zipper closure
- Chunky platform
- Tall block heel
- Lace-up back detail
- Faux suede material
Style Number/Barcode: 07403-0345
Category Name: Night Out
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jennie Formal Open Back Sequin Dress
Special Occasion
Dazzle in a sequin dress that shimmers from all your best angles! Jennie features a trendy V-neckline, a double row of sleek spaghetti straps, a sexy strappy open back, and shimmering sequins set in a geometric pattern. Complete your statement formal outfit with sleek stiletto heels and duster earrings.
Fit & Features
- Sleeveless V-neckline
- Double-row of spaghetti straps
- Open back accented with sleek cross straps
- Sequins set in a geometric design
- Mini-length silhouette
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05001-0490
Category Name: Night Out
Price: $29.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On Point Lace Up Stiletto Booties
Lace-up in chic booties to keep your look on point! Perfect for your next GNO or your next date night with bae. The booties feature a trendy lace-up front to create a customized fit, a pointed toe, and a sleek stiletto heel. Complete your look with a sweater dress and moto jacket.
Fit & Features
- Around the ankle fit
- Lace-up front
- Inner zipper closure
- Pointed toe
- Stiletto heel
- Faux microsuede material
Please be advised that these booties run small. Fit model recommends sizing one size up.
Style Number/Barcode: 07403-0318
Category Name: Night Out
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lace Up Peep Toe Stiletto Booties
Lace-up in these booties that elevate your looks this season! They feature a zippered back, a cutout lace-up front, peep toe, and a sleek stiletto heel. Complete your look with high waist pants and a chunky cable knit sweater.
Fit & Features
- Ankle-length
- Zippered back
- Cutout lace-up front
- Peep toe
- Stiletto heel
- Faux suede material
Style Number/Barcode: 07403-0342
Category Name: Night Out
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free