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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Nadine Formal Sequin Midi Dress
Special Occasion
Stand out in sequins as you wow them all in our Nadine sequin dress!
Fit & Features
- V-Neckline I Padded Cups
- Spaghetti Straps
- Midi Length Silhouette With Split At Center Back
- Lined Mesh Fabric With Sequins Throughout
- Form-Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0265
Category Name: Night Out
Price: $20.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rowena Formal Heat Stone Mini Dress
Special Occasion
Sparkle up the night like the goddess you are in our shimmering Rowena dress! Her heat stones will add a sparkle to your glow!
Fit & Features
- V- Neckline
- Adjustable Spaghetti Straps
- Gemstones
- Heat Stones
- Geometric
- Fully Lined Mesh
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05103-0423
Category Name: Night Out
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kayley Sequin Midi Dress
Special Occasion
Have a night to remember in our Kayley! She features a wired deep v neckline, double adjustable spaghetti straps that lead to a criss-cross back, padded cups, and a fully lined form-fitting silhouette that offers a moderate stretch. She has a zipper located center back and is composed of a mesh material that is adorned in sequins! Her hem hits mid-length and she features a small slit at the back. Complete look with a sleek clutch.
Fit & Features
- Wired V-neckline with padded cups
- Double row adjustable spaghetti straps
- Criss-cross back
- Sequins
- Midi length silhouette with small center slit at the back
- Fully lined mesh fabric
- Form hugging fit, moderate stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0262
Category Name: Night Out
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me Out Pencil Midi Skirt
We are going to take you out on a hot date, because your outfit is F-I-R-E ! This midi skirt is designed with all the curve flattering details that we love. A high waistline, a curve hugging silhouette, and a high thigh slit. Hem hits passed the knee, and midi is composed of a woven knit material that offers moderate stretch. Zipper located mid back.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06401-0070
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Say It Again Mini Dress
Sultry and stylish, you can say that again!
Fits & Features
- Spaghetti Straps That Lead To An Open Back With Lattice Detail
- Wrap Front V Neckline
- Ruching At Waist
- Short Asymmetrical Hem
- Smooth, Stretchy Knit Fabric
- Curve-Hugging Fit
Style Number/Barcode: 05101-0298
Category Name: Night Out
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Turtleneck Ribbed Knit Mini Dress
This ribbed knit mini is the perfect dress for transitioning into the colder months! It features a sleeveless bodice, a turtleneck, and a short, mid-thigh length with a curve hugging fit. The ribbed knit fabric offers plenty of stretch.Style Number/Barcode: 05102-0317
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Eye Spy Peep Toe Booties
You've got style game from head to toe—and we see you! Keep the momentum in these chic faux suede booties. Shoes feature a rounded peep toe, a lace-up tie front, an interior side zipper, a sturdy block heel, and a mid-height shaft.Style Number/Barcode: 07403-0156
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Fringe Rhinestone Earrings
Make a statement with these earrings that will make your add a unique touch to your look! Earrings feature an oval on post and a bohemian fringe design adorned with mini rhinestones. Includes a post back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0089
Category Name: Night Out
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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A Star Is Born Earrings
You're a natural born star babe! These earrings are a star shape adorned with rhinestones. They have a post back closure and are open ended. Get your shine on!
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0132
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Aerin Formal Sequin Midi Dress
Special Occasion
Have a night to remember in our Aerin! She features a boat neckline, long sleeves, and a sexy low back with a zipper closure. She is fully lined and composed of a mesh material that offers a form fitting silhouette and slight stretch. Her mid length hemline hits mid calf, and she features a high slit at one side that makes her easy to walk and dance in! She showcases a beautiful sequin swirling pattern throughout that gives an elegant finish!
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: 05001-0267
Category Name: Night Out
Price: $27.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crazy For Rhinestones Wristlet
This wristlet is the star of the show. Composed of a mesh material and adorned in rhinestones, purse has a snap closure as well as a zipper closer. Purse is lined with a satin material, and is a medium size. This baby is blindingly gorgeous!Style Number/Barcode: 07204-0109
Category Name: Night Out
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Touch Of Gold Velvet Thigh High Boots
There's no harm in adding a touch of gold to your look! These velvet boots are designed with an almond toe, a zipper closure, a thigh high fit with an elasticity that keeps them in place, and a high golden block heel.Style Number/Barcode: 07402-0058
Category Name: Night Out
Price: $23.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Danica Long Formal Gown
Special Occasion
Introducing our Danica gown! She has a little edge, she has a little sex appeal, and she has a lot of intricate detailing!
Fit & Features
- Sweetheart neckline
- Deep V notch | Padded cups
- Crepe
- Side slit
- Long hemline
- Back keyhole cut out I Adjustable self-ties
- Fitted silhouette | Moderate stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0371
Category Name: Night Out
Price: $20.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glow Girl Sequin Midi Dress
Glow on with your bad self! Flaunt your pretty self in this captivating dress.
Fits & Features
- Adjustable Shoulder Straps
- Sweetheart Neckline
- Zipper & Hook And Eye Closure At Back
- Iridescent Sequins, Mesh Knit Fabric I Fully Lined
- Midi Length Silhouette
- Curve Hugging Fit I Ample Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0293
Category Name: Night Out
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Galore Midi Dress
Slay all day in the Glitter Galore midi dress!
Fits & Features
- Sweetheart Neckline
- Double Strap Hook & Eye Closure At Back
- Cut-Out Details Along Sides And Back
- Fully Lined, Glitter Knit Composition
- Curve-Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0294
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Mesh Rhinestone Stiletto Booties
Sparkle every step of the way in the Glitter Mesh Rhinestone Stiletto booties. These booties feature a point toe, zipper closure at the side, and a skinny stiletto heel. They're composed of a glitter mesh material with shimmery rhinestone detailing.
Style Number/Barcode: 07403-0148
Category Name: Night Out
Price: $27.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Goals Sequin High Waist Shorts
You'll be strutting your glow, everywhere you go. Perfect the look by picking up the matching blazer!
Fits & Features
- High Rise Waist
- Sequined Mesh Knit
- Fully Lined
- Form-Fitting Shorts
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Zipper & Hook And Eye Closure At Center Back
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06403-0047
Category Name: Night Out
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Open Back Peep Toe Booties
Step in the right direction with a pair of heels that command the room! Designed with a peep toe, an open back and an ankle fit. They feature a gold block heel that adds just the touch we were looking for! Composed of a nylon material and include a zipper closure.Style Number/Barcode: 07403-0152
Category Name: Night Out
Price: $22.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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Young And Free Velvet Blazer
You have a vintage style, but a young and free soul! This blazer has all that wrapped in one! Pair with your fav lil' black dress, or dress down with a basic tee and high waist bottoms!
Fit & Features
- Collared neckline
- Open design | Hook and eye closure
- Long sleeves
- Ribbed velvet material
- Moderate stretch
- Form fitting
- No pockets | Unlined
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small
Style Number/Barcode: 06204-0251
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Woven Bell Sleeve Tie Front Top
Bell sleeves are the way to go babe! This woven tie front top is perfect for layering over all your cute 'fits.
Fit & Features
- Long flowy bell sleeves
- V neckline
- Tie front closure
- Cropped
- Lightweight, woven fabric
- No stretch
Style Number/Barcode: 06204-0249
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vada Lace-Up Formal Midi Dress
Special Occasion
Create a polished yet sexy look for yourself in our Vada! She features a wired deep v neckline, spaghetti straps that lead to a lace up back detail and a lower back zipper closure with a hook and eye to keep her in place. Bodice is designed with a gathered pleating at the bust, and leads down to a mid length hemline and a high slit at one side. She is fully lined and composed of a crepe material that offers moderate stretch and a form fitting silhouette.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0259
Category Name: Night Out
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Valencia Formal Midi Dress
Special Occasion
Make a lasting impression in our Valencia! She is uniquely designed with an asymmetrical neckline, one long sleeve, and one sleeveless tank strap. Her bodice is fitted and leads down to a mid length hemline, and a high thigh slit. She has a zipper closure located center back with a hook and eye closure to keep her securely in place. She is composed of a crepe material and is fully lined offering moderate stretch and a form fitting silhouette.
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0260
Category Name: Night Out
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Camryn Sweetheart Long Gown
Special Occasion
Start off your special night with the perfect attire. Introducing our Camryn, designed with a deep sweetheart neckline, off shoulder sleeves, and a form fitting silhouette. The ruching down the center gives a flattering curve hugging detail and shows a high slit up the center. Her hem is floor sweeping and she is composed of a crepe material that offers moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0375
Category Name: Night Out
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free