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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Effortlessly Sultry Bell Sleeve Crop Top
Create an effortlessly sultry everyday look with this trendy crop top! It features long bell sleeves that can be worn off-the-shoulder, halter spaghetti straps, a square neckline with a center cutout at the bust, and a fitted, cropped hem with an angled front design. The brushed knit fabric offers plenty of stretch. Style with high-rise jeans and mules.
Fit & Features
- Long bell sleeves, can be worn off-the-shoulder
- Halter spaghetti straps, tie-back closure
- Square neckline, center bust cutout
- Fitted, angled, cropped hem
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4702
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vibe In Marabou Halter Crop Top
You and this halter crop top will totally vibe together for dinner, drinks, and date nights! The sleeveless top features a halter neck with tie-back closure, a partial open-back, and a marabou feather trim hem. Style with chic flare pants and heels.
Fit & Features
- Sleeveless halter neck
- Tie-back closure
- Partial open-back
- Marabou feather trim
- Cropped hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4542
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Trendsetter Strappy Block Heels
Become the major trendsetter of your squad in these stylish strappy block heels! They feature a clear toe strap and a wrap-around design with a tie back closure. Pair these heels with some high rise mom jeans for a casual-chic vibe.
Fit & Features
- Open almond toe
- Clear PVC toe strap
- Wrap-around design with tie back closure
- Closed ankle
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2448
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twist Front Ribbed Knit Mini Dress
Create a fab moment in a twist knot dress! The dress features a V-neckline with a twist knot accent, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit. Complete your look with clear mules.
Fit & Features
- V-neckline with twist front accent
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 06005-0700
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Light Up The Night Glitter Lurex Tie Waist Top
This shimmering top is what you need to illuminate your date night. The top features a cowl neckline, cap sleeves, a tie waist hem, and composed of a lurex glitter knit fabric. Complete your look with a faux leather mini skirt.
Fit & Features
- Cowl neckline
- Cap sleeves
- Tie waist hem
- Glitter lurex fabric
- Form hugging fit
- Moderate stretch
The saturation of glitter varies. Glitter may transfer.
Style Number/Barcode: 06001-2934
Category Name: Night Out
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Gorgeous Sparkle Rhinestone Hoop Earrings
These glitzy rhinestone hoop earrings will bring a gorgeous sparkle to your looks! They feature a large metal hoop design with all-around rhinestone embellishments. Include an omega closure. Style these hoop earrings with a glitter clutch for a night out.
Fit & Features
- Large metal hoop design
- Rhinestone embellishments
- Omega closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1708
Category Name: Night Out
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
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Drawn To You One-Shoulder Mini Dress
Everyone will be drawn to you in this chic one-shoulder mini dress! It features stylish ruched detailing, a drawstring at the hem, and a short, curve-hugging silhouette. Pair this dress with clear heels and a sleek clutch for your next night out.
Fit & Features
- Sleeveless one-shoulder neckline
- Ruched detailing
- Drawstring at the hem
- Mini-length, form-hugging fit
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3784
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Rush Ruched Mini Dress
Get caught in a floral rush with a pretty mini dress! The dress features a floral print, a sleeveless V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a drawstring. Complete look with clear heels and butterfly hoops.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Ruched body
- Mini length silhouette with drawstring
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1035
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Beauty Satin Slip Dress
Showcase your beauty in this sleek satin slip dress! It features a sleeveless low V-neckline, a knot front design with dual waist cutouts, adjustable spaghetti straps, and a mini-length, relaxed fit. Style this dress with clear heels.
Fit & Features
- Sleeveless V-neckline
- Knot front design, dual waist cutouts
- Adjustable spaghetti straps
- Hidden back zipper and hook and eye closure
- Mini-length, relaxed fit
- Satin fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1333
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sound The Alarm Ruched Midi Dress
Raise the heat in a sexy midi dress for your date night with bae. The midi dress features a sleeveless square neckline, adjustable spaghetti straps, ruching throughout, and a midi-length silhouette. The dress is composed of a lined mesh knit fabric that offers a form hugging fit with a slight stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline, padded cups
- Adjustable spaghetti straps
- Ruching
- Midi length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1359
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All That Glistens Cowl Neck Bodysuit
Own your glisten and glow! Shine bright in this cowl neck bodysuit showcasing a sultry, sleeveless bodice, rhinestone straps that cross along the open-back design, a thong cut bottom with dual button-snap closures. Complete the look in trendy jeans and mules.
Fit & Features
- Sleeveless, cowl neck
- Rhinestone straps
- Open-back, cross strap design
- Thong cut bottom, dual snap-button closures
- Slinky knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4409
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Night Sparkle Crepe Rhinestone Dress
Sparkle all night in this crepe mini dress showcasing a dazzling rhinestone trim along the sleeveless bodice! It features adjustable spaghetti straps, a sweetheart neckline, a padded bust, and a side pleated seam to accentuate your curves along the asymmetrical hem. Complete the look in this mini-length dress with an embellished clutch.
Fit & Features
- Sleeveless sweetheart neck, adjustable spaghetti straps
- Rhinestone trim bodice, padded bust
- Back zipper and hook-eye closure
- Bodycon silhouette
- Side pleated seam, asymmetrical mini hem
- Crepe-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4688
Category Name: Night Out
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Standout Satin Cutout Midi Dress
Standout in this sultry satin midi dress at an upcoming cocktail soiree or dressy celebration! The dress features a sleeveless crew halter neckline with dual button closures, a flirty bust cutout, dual waist cutouts, and a bodycon silhouette. Complete the look in rhinestone spiral heels for a dazzling effect!
Fit & Features
- Sleeveless crew halter neckline, dual button closures
- Bust cutout, back zipper closure
- Dual waist cutouts
- Bodycon silhouette
- Midi-length hem
- Smooth satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2435
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oh-So-Sleek Satin Slip Chemise Dress
Oh-so-sleek, this satin slip chemise dress will create a sexy-chic look. Designed from a silky-satin fabric with a dainty scalloped trim, it features a sleeveless V-neckline, adjustable spaghetti straps leading to a cross-back design, a mini-length hem with a side slit, and an A-line silhouette. Style with a cozy robe for a night it, or layer on a faux leather jacket for a night out!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back design
- Mini-length hem, side slit
- A-line silhouette
- Satin fabric, scalloped trim, no stretch
- Runs true to size
Style Number/Barcode: 07103-0997
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Top Of The Trends Belted Cargo Mini Skirt
Stay on top of the trends in this cute and casual cargo mini skirt! It features a mid-rise waist, a belted design with double grommet detailing, cargo-style pockets on each side, a mini-length hem, and a form-fitting silhouette. The woven fabric offers a moderate stretch. Style this cargo mini skirt with a basic bodysuit, hoop earrings, and clear mules!
Fit & Features
- Mid-rise waist
- Belted design, double grommet detailing
- Dual front button closures, hidden zipper closure
- Dual cargo pockets
- Mini-length hem, form-fitting silhouette
- Cotton-blend woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0206
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Fling High Slit Ditsy Floral Knit Midi Dress
Embrace your flirtatious side in this adorable floral knit midi dress! The lightweight stretchy knit fabric is detailed with the cutest ditsy floral print pattern for the spring season. The mid-length dress features a crew neckline, short sleeves, a small back keyhole cutout, a large lower back cutout to add some allure, a high-cut front slit, and a bodycon silhouette to flaunt your curves. Style with hoop earrings and a charm necklace.
Fit & Features
- Stretchy knit fabric
- Ditsy floral print
- Crew neckline, short sleeves
- Back keyhole cutout, lower back cutout
- High front slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5653
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Style So Sleek Faux Leather Stiletto Heels
Create a going-out style radiating sleek vibes with these faux leather stiletto heels! They feature an open square-shaped toe with a dual toe strap design, dual ankle straps with adjustable buckle closure, a closed back, and a thin stiletto heel. The bronze heels are made with patent faux leather, and the silver heels are made with metallic faux leather. Pair with an envelope clutch for your next night out.
Fit & Features
- 4" Stiletto heel
- Open square toe, dual toe straps
- Dual ankle straps with buckle closure
- Closed back
- Bronze heels are patent faux leather
- Silver heels are metallic faux leather
- Runs true to size
Style Number/Barcode: 07401-4893
Category Name: Night Out
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- 4" Stiletto heel
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Time To Party Strappy Mini Dress
Style up this sassy strappy mini dress for your weekend party! It features a sleeveless sweetheart neckline with a center-notched accent, front straps that can be worn in a tie-back halter design or as a cute tie-front accent, adjustable spaghetti straps, a short, curve-hugging silhouette, and a front slit. The crepe fabric has a moderate stretch. Complete the look with clear lucite heels.
Fit & Features
- Sleeveless sweetheart neckline, center-notched accent
- Front straps that can be worn multiple ways
- Adjustable spaghetti straps
- Back zipper, hook and eye closure
- High waist seam
- Mini-length hem, front slit
- Crepe fabric, lined bust, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4623
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Statement Strapless Ruffle Mini Dress
Little black dress, bold statement! Step out and stun in this strapless mesh mini dress featuring a sweetheart neckline, a ruched and lightly padded bust, and a front ruffle trim along the bodycon silhouette. Complete the look in platform heels for a dressy birthday party!
Fit & Features
- Strapless sweetheart neckline
- Ruched and lightly padded bust
- Bodycon silhouette
- Front ruffle trim
- Mini-length hem
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2545
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tanya Pearl-Trim Velvet Dress
Special Occasion
Showcase that beautiful back in our simply stunning velvet Tanya dress! She features a round neckline, long sleeves, a seamed bodice, a dramatic open back with rows of pearls and clear rhinestones snaking the periphery, and a slim pencil skirt. Tanya has a bodycon construction and is made from a tactile velvet material with 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: 05001-0137
Category Name: Night Out
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On The Run Thigh High Boots
Girl you are runnin through our mind in a pair of thigh highs! These on trend boots are designed with an almond toe, a tall heel, and a lace up detail at the back. They have a zipper closure and are composed of a faux suede material.Style Number/Barcode: 07402-0084
Category Name: Night Out
Price: $23.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Cat Leopard Off Shoulder Mini Dress
Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Cuffed Long Sleeves
- Elastic, Smocked Skirt
- Subtly Pleated, Mini-Length Hemline
- Form-Hugging Fit WIth Plenty Of Stretch
Style Number/Barcode: 05102-0397
Category Name: Night Out
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plunging Tie Strap Basic Bodysuit
Update your basic bodysuit with pretty tie-straps. This basic bodysuit features a plunging V-neckline, tie shoulder straps, and a plunging scoop back. The bodysuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete your baddie basic look with high waist jeans and extra-large hoops.
Fit & Features
- Plunging V-neckline
- Tie shoulder straps
- Plunging scoop back
- Smooth knit fabric
- Form hugging fit
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2724
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bling It On Sequin Ruched Mini Dress
Bring on the bling in this stunning sequin ruched mini dress! Featuring allover sequin embellishment and a curve-hugging fit, this dress is a must-have for a girl's night out. Pair with some dazzling duster earrings to complete your it-girl look.
Fit & Features
- Adjustable spaghetti straps
- Square neckline
- Back zipper closure
- Ruched detailing
- Side tie at hem
- Short, form-hugging fit
- Sequin adorned fabric
Style Number/Barcode: 05103-0779
Category Name: Night Out
Price: $18.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance