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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Edgy Chic Ponte Knit Joggers
Edgy chic is the total vibe with these ponte knit joggers! Pair with a graphic tee and some combat boots for that it girl look.
Fit & Features
- High rise waist
- Belt loops
- Front hidden zipper and dual hook and bar closures
- Two slanted front pockets | Two faux back pockets
- Included chain accent
- Elastic jogger hem
- Ponte knit fabric | Moderate stretch
Style Number/Barcode: 06502-0319
Category Name: Night Out
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flutter Me Up Tie Waist Jumpsuit
Slip into this effortless jumpsuit and get buttered up with compliments! It's the perfect desk-to-dinner look!
Fits & Features
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Short Flutter Sleeves
- V Neckline I Princess Seams
- Back Zipper
- Tie Waist
- Wide Leg Openings
- Crepe Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 06502-0316
Category Name: Night Out
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Short Flutter Sleeves
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Faux Leather Lace Up Pants
Lace up in these edgy pants to make a bold statement! Perfect for the rocker in you, pair with a graphic tee and combat boots for a festival-ready look!
Fit & Features
- Mid-Rise Fit
- Lace-Up Front
- Faux Front Pockets | Back Pockets
- Lined Faux Leather Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 06402-0170
Category Name: Night Out
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Staple High Waist Shorts
Keep a staple pair of shorts on the back burner at all times! You are able to style with a simple tank, or dress up with a nice bodysuit and heels!
Fit & Features
- High waist fit
- Large pockets
- Stretch backing
- Linen material | Non- stretchy material
Style Number/Barcode: 06403-0084
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Something In The Way Satin A-line Mini Skirt
There's something in the way you wear that mini skirt that gives us heart eyes bae! Keep it classy and pair with a puff sleeve bodysuit, or dress down with a graphic tee and boots!
Fit & Features
- High waist fit
- Faux wrap design
- Tie detailing at the hip
- A-line design
- Mini skirt hemline
- Satin | No stretch
Style Number/Barcode: 06401-0206
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go On Faux Wrap Mini Skirt
Go on with your bad self! Work this skirt in several different ways. Tuck in a printed blouse, your fave top, or even a lightweight sweater...girl, the possibilities are endless!
Fits & Features
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High Rise Waist
- Back Zipper
- Faux Wrap Front Design | Mini Length
- Crepe-Like Fabric
- Moderate Stretch
Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06401-0205
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Waist
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Super High Rise Skinny Ponte Pants
Everything feels better when you make it high waist! Style these ponte stretch bottoms with all of your work wear favs, or dress them up with a leather jacket and heels for a fun night out!
Fit & Features
- Super high rise
- Button + zipper closure
- Faux front pockets
- Functioning back pockets
- Ponte material | Slight stretch
- Skinny tapered leg
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06502-0317
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Shoulder Power Jumpsuit
Take on the day and night in a jumpsuit that gives you all the power! Pair with a pair of heels and stunning earrings and you are ready to roll!
Fit & Features
- V-neckline
- Ruffled cap sleeves
- Form fitting silhouette
- Flared leg
- Crepe material | Moderate stretch
- Lined
- Criss cross back detailing
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.Style Number/Barcode: 06502-0314
Category Name: Night Out
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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It Girl Super Platform Block Heels
These super platform block heels will totally showcase your it girl status! They feature a tall platform with a sturdy block heel. Get ready to strut in these gorg heels paired with an adorable skater dress and rhinestone earrings!
Fit & Features
- Open toe | Toe strap
- Adjustable around the ankle thin strap
- Closed back
- Tall platform
- Sturdy block heel
- Nubuck material
Style Number/Barcode: 07401-2193
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Sleek Vibe Mini Skirt
Get such a sleek & chic vibe in this sexy faux leather mini! The skirt's croc embossed print adds an extra edge.
Fit & Features
- High rise waist
- Back zipper closure
- Two vertical front seams leading to small slits
- Short, form hugging fit
- Croc embossed PU fabric
- Moderate stretch
Style Number/Barcode: 06401-0204
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Point Ruched Mini Skirt
Keep your look on point with a ruched mini skirt! Easily style with a sweetheart top, and a pair of strappy heels!
Fit & Features
- High waist fit
- Ruched design
- Drawstring hip
- Zipper center back
- Lined | Mini skirt hemline
- Mesh overlay | Moderate stretch
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06501-0234
Category Name: Night Out
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Diva Sleeveless Catsuit
Showcase your fashion diva side in this trendy denim catsuit! It features a sleeveless bodice, tank straps, a V neck and back, and a back zipper closure. The high waist leads to form-fitting pant legs, offering a curve-hugging style. The denim fabric offers moderate stretch. Complete your look with a chic necklace and heels.
Fit & Features
- Tank straps
- V neck and back
- Back zipper closure
- High waist
- Fitted pant legs
- Form-hugging fit
- Denim fabric with a moderate stretch
Style Number/Barcode: 06602-0088
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrapped In Glamour Ruched Glitter Mini Dress
Wrap yourself in a glam mini dress that brings the glow to your next GNO! The dress features a wrap V-neckline, long sleeves, and a mini length silhouette with a ruched envelope hem. Complete your look with silver heels.
Fit & Features
- Wrap V-neckline
- Long sleeves
- Glitter knit fabric
- Mini length silhouette
- Ruched envelope hem
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05101-0700
Category Name: Night Out
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Asymmetrical Maxi Skirt
Take it to the next level and show off a sultry and edgy look in this maxi skirt! Top it off with your fave crop top, add a denim jacket, and slip into some chic booties!
Fits & Features
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High Rise Elastic Waistband
- Smooth Jersey Knit Fabric
- Maxi Length Silhouette
- Asymmetrical High Slit
- Ample Stretch | Form Hugging Fit
Style Number/Barcode: 06501-0227
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Elastic Waistband
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Wrapped In Suede Mini Skirt
Add some texture to your OOTD with this adorable faux suede mini skirt! It features a flattering high-rise waist with a faux wrap-front design and a short, form-hugging fit. Elevate your casual 'fit by pairing this skirt with a graphic tee.
Fits & Features
- High-rise waist
- Hidden back zipper closure
- Short, faux wrap-front design
- Mini-length silhouette
- Form-hugging fit
- Faux suede fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0199
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- High-rise waist
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Zip It Coated Faux Leather Mini Skirt
Zip up into this sleek and chic coated faux leather mini! Pair with an edgy graphic tee and some booties for a girly rocker look!
Fit & Features
- High rise waist
- Asymmetric complete zip front
- Zippered faux pockets
- Short, form hugging fit
- Coated faux leather fabric
- Moderate stretch
Style Number/Barcode: 06401-0203
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fit For A Flattering Finish Sleek Jumpsuit
Looking for a flattering finish? This sleek straight leg jumpsuit is the way to go! Starting off at a form fitting silhouette and leading down to a wide leg it is easily paired with heels and gives you that tall sleek finish!
Fit & Features
- One piece
- V-neckline
- Adjustable spaghetti straps
- Square back with bar cut out detailing
- Wide straight leg
- Vertical seams at the bodice
- Slip on fit
- Crepe | Moderate stretch
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06502-0313
Category Name: Night Out
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace Go Side Slit Mini Skirt
You got places to be and people to see! Slay it by pairing this with a basic white tee and leather jacket!
Fits & Features
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High Rise Elastic Waistband
- Mini Length Silhouette
- Front Slit
- Crochet Lace Overlay | Fully Lined
- Plenty Of Stretch
Style Number/Barcode: 06501-0229
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Elastic Waistband
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She's That It Girl Knit Catsuit
Yes babe, be that total it girl in this comfy cute knit catsuit! Pair with some heels and a faux leather jacket to really amp up the look.
Fit & Features
- Spaghetti straps
- Wrap front V neckline
- High rise elastic banded waist
- Faux tie front
- Skinny pant legs
- Knit fabric | Plenty of stretch
- Form hugging fit
Style Number/Barcode: 06502-0312
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spot On Polka Dot Organza Sleeve Bodysuit
Your outfit is lookin' spot-on! Layer it over your fave bralette and bandeau.
Fits & Features
- Scoop Neckline
- Sheer Organza Short Sleeves With Elastic Cuffs
- Slit At Center Back I Button Closure At Nape
- Sheer, Unlined Polka Dot Bodice
- Stretchy Knit Thong Bottom With Dual Button Snap Closure
- Relax Fit I Minimal Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0712
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Lace Up In Mesh Crop Top
Lace up in this sheer must have top! Pair with edgy pants and sleek stilettos for a look that's squad-approved!
Fit & Features
- Mock Neck
- Sheer Unlined Long Sleeves
- Lace-Up Keyhole
- Cropped Hem
- Partially-Lined Mesh Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 06001-2433
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow Getter Glitter Knit Ruched Mini Dress
Capture that glow, girl! This mini dress dazzles from all your best angles for your celebration! The dress features a plunging V-neckline, a ruched body, 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 black heels.
Fit & Features
- Sleeveless V-neckline, wrap-front design
- Spaghetti straps
- Back zipper and hook and eye closure
- Ruched body, mini-length silhouette
- Sheer glitter knit fabric, full lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-0778
Category Name: Night Out
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's A Queen Lace Detail Mini Dress
You're such a chic & stylish queen, and everyone will bow down to you in this pretty lace detail mini dress! Paired with some strappy stilettos, you'll rule the room.
Fit & Features
- Adjustable spaghetti straps
- Padded sweethart neckline | Lace trim
- Center lace bodice detail | High waist
- Back zipper | Hook and eye closure
- Short, form hugging fit | Tulip hem with ruched detailing
- Crepe fabric | Moderate stretch
Style Number/Barcode: 05101-0698
Category Name: Night Out
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free