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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All The Feels Studded Butterfly Block Heels
A pair of whimsical-inspired butterfly block heels that'll make your style soar! Pair with a mini handbag and earrings.
Fit & Features
- Block heel
- Open almond toe
- Multi-asymmetrical strap design
- Studded butterfly accent
- Adjustable ankle strap with buckle
- Black: Faux microsuede material
- Silver and Gold: Faux metallic leather material
- Runs true to size
Style Number/Barcode: 07401-5101
Category Name: Night Out
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So The Drama Distressed Faux Leather Under-The-Knee Boots
Bring the drama in these faux leather under-the-knee boots designed in a trendy scrunched design. Pair with leggings.
Fit & Features
- Faux leather fabrication, metallic finish
- Under-the-knee fit
- Closed pointed-toe
- Scrunched body
- Runs true to size
Style Number/Barcode: 07402-1090
Category Name: Night Out
Price: $19.97 $55.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Impression Swirl Mini Skirt
Express your inner artsy side in this unique mini skirt featuring a high-rise elastic waist, bodycon silhouette, and a flocked velvet swirl pattern on mesh fabric with a knit lining. Style with a basic long sleeve bodysuit to complete the look!
Fit & Features
- High-rise elastic waist
- Bodycon silhouette
- Mini-length hem
- Flocked velvet swirl pattern
- Mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0794
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Twice The Sparkle Mini Skirt
It's twice the sparkle in just in time for the holiday season! This sequin mini skirt brings glam and trendiness in a high-rise waist and bodycon silhouette. Complete the look in the matching top.
Shop The Matching Top: Twice The Sparkle Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Mini-length hem
- Sequin knit fabric, partial lining, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0737
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Let's Party Satin Low-Heel Mules
These sassy satin low-heel mules were made to create glam party looks. They feature an open square toe, a wide toe strap, an open back for easy on-and-off styling, and a low block heel for comfortable wear so you can dance all night long. The smooth satin material will show off a stunning sheen. Complete your 'fit with a rhinestone clutch.
Fit & Features
- Open square-shaped toe
- Wide toe strap
- Open back
- Low block heel
- Satin material
- Faux leather subtle cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4216
Category Name: Night Out
Price: $9.96 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Scale Back Snake Tie-Front Top
Scale back your GNO fit and keep it sultry and sleek in this snake print crop top featuring peasant sleeves, a plunge v-neckline, and a tie-front closure. Style with faux leather leggings and mules.
Fit & Features
- Peasant sleeves
- Plunge v-neckline
- Tie-front closure
- Snake print
- Fits true to size
Style Number/Barcode: 06204-1404
Category Name: Night Out
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charm Them All Midi Dress
Charm them all in this casual yet so cute printed midi! The dress features a sleeveless bodice, spaghetti straps, a rounded neckline, and a mid-length, curve hugging fit. The dress is composed of a knit fabric with plenty of stretch.
Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small.
Style Number/Barcode: 05102-0252
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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O-Ring Waist Cut Out Mini Dress
Chic with a trendy edge to the look, this mini dress will amp up your style. It features long sleeves with elastic cuffs, a deep V neckline, a hidden back zipper closure, a waist cut out with a front O-ring detail, and a flowy short skirt with a hidden back zipper. The dress is composed of a chiffon fabric and includes a stretchy knit lining.Style Number/Barcode: 05101-0241
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Velvet Mini Skirt
Shop Matching Top: Snake Print Velvet Tank Top
Be a total vixen in velvet with this snake print mini skirt! It features a high rise elastic banded waist paired with a short, curve hugging fit. The smooth velvet fabric has moderate stretch. Don't forget the matching tank top!
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06501-0109
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heat Check Halter Mini Dress
This dress is serving bold and unforgettable—cowl neckline in the front, daring open back in the rear. Sleek, sultry, and fitted to perfection, it’s your ultimate night-out pick.
Fit & Features
- Stretch knit fabric
- Halter neckline with cowl front
- Open strappy back detail
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05103-000484
Category Name: Night Out
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Marabou Crop Top
Girl you're extra! Show off your affinity for the fancier things with this statement top! It features an off the shoulder neckline with a marabou trim, long sleeves and a cropped hem. Top is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0059
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Above Casual Coated Midi Pencil Skirt
For the gal that likes to be a little above the everyday casual look! This midi skirt is designed with a high waist-line, and a slit located center back which makes the skirt easy to walk around in. Midi is composed of a coated smooth knit material that offers moderate stretch and a form fitting silhouette. Zipper located back of skirt.
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.Style Number/Barcode: 06401-0091
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Little Sparkle Platform Heels
Finish your look with a touch of sparkle! These high heels are designed with an almond toe, a rhinestone band across and, a closed heel with a thin ankle strap that has an adjustable pin buckle closure. Heels are composed of a faux nubuck material and offer a short platform, and a high heel.Style Number/Barcode: 07401-0728
Category Name: Night Out
Price: $22.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sarina High Slit Sequin Midi Dress
Special Occasion
Highlight your beauty with our mesmerizing Sarina dress! You'll illuminate every room!
Fits & Features
- Bungee Shoulder Straps Leads To Racerback Design With Zip Closure
- Plunging V Neckline
- Slim Fit Bodice
- Midi Length Silhouette With Thigh-High Slit
- Fully Lined Mesh Fabric With Sequins Throughout
- Curve-Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0264
Category Name: Night Out
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Zip Front Snake Print Coated Leggings
Edge it up a little with these trendy snake print coated leggings!
Fit & Features
- High rise elastic banded waist
- Front zipper with small O-ring detail
- Form-fitting pant legs
- Snake print
- Coated knit fabric
- Moderate stretch
Style Number/Barcode: 06502-0259
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Live For The Shine Rhinestone Heels
We are livin' for that shine, and these rhinestone heels are just the touch!
- Faux suede heels
- Open almond toe
- Ankle + Toe band with rhinestone detailing
- Zipper back of heel
- Block heel
- Small island platform
Style Number/Barcode: 07401-0478
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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You Glow Girl Glitter Mini Dress
You glow on girl in this shimmering mini dress! Pair this baby with statement pumps and a pop of highlight for an Insta-ready look!
Fit & Features
- V-Neckline | Pleated Cups
- Spaghetti Straps
- Mini Length Silhouette
- Mini Side Slit
- Lined Glitter Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05103-0681
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bad Intentions Lace Up Latex Crop Top
We've got a little baddie on our hands! Embrace your edgy side, and don't forget to pick up the matching lace up bottoms!
Shop Matching Bottoms: Bad Intentions Double Lace Up Latex Briefs
Fit & Features
- Tank straps
- Round neckline
- Cropped hemline
- Princess seams
- Lace up eyelet detail center bodice
- Shiny latex finish
- Faux leather
Style Number/Barcode: 06003-0670
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Catch Me Cropped Mesh Top
Get caught in mesh girl! Create a fabulously sheer lewk in this chic crop top! Pair with high waist skinny jeans and fab pumps for head-turning appeal!
Fit & Features
- Round Neckline
- Sweetheart Bust Lining
- Fitted Long Sleeves
- Partially Unlined Mesh Fabric
- Cropped Hem
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 06001-2468
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fab and Fierce Fringe Open Back Mini Dress
Keep it fab in a fringe dress that impresses with each turn for your night out! The dress features a scoop neckline, a daring matching scoop back with a fringe accent, and a mini length silhouette. The dress is composed of a retentive crepe fabric that offers a form hugging fit and a moderate stretch. Complete your look with black rhinestone heels.
Fit & Features
- Sleeveless scoop neckline
- Scoop open back
- Fringe
- Mini length silhouette
- Crepe fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05103-1059
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Show off Chain Block Heels
Show off your flawless style in these bomb heels! The PU heels feature an open square toe, a single PVC toe strap and a gold chain detail around the ankle. Pair them with a sexy mini dress and hoops for the perfect GNO look.
Fit & Features
- PU material
- PVC toe strap
- Block heel
- Chain ankle strap
- Runs true to size
Style Number/Barcode: 07401-2876
Category Name: Night Out
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The A-List One Shoulder Glitter Dress
Stun like the A-lister you are with a mini dress that brings the shine to your night out! The dress features a one-shoulder neckline, a fitted long sleeve, a sexy waist cutout, and a mini-length silhouette. The dress is composed of a glitter knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels and statement earrings.
Fit & Features
- One-shoulder neckline
- Fitted long sleeve
- Waist cutout
- Mini length silhouette
- Glitter knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3868
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Cross Charm Layered Necklace
Layer on the charm with a cute necklace that adds that finishing touch to your outfit! The necklace features a layered design with a rhinestone embellished cross charm and a mini cross charm lariat. Complete look with a crop top and mini skirt set.
Fit & Features
- Layered design
- Rhinestone embellished cross charm
- Mini cross charm lariat
- Lobster clasp closure
Style Number/Barcode: 07002-0901
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale