Night Out

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.

  • Ring The Alarm Mini Skirt

    Sound the alarm in this hot mini skirt! The high waist skirt features an all-over faux coated leather, vertical seams to create an hourglass illusion, and a mini length that offers a form-hugging fit with a moderate stretch. Complete this head-turning look with a chic crop top and a pair of booties.

    Fit & Features

    • High-rise waist
    • Vertical seams
    • Mini-length silhouette
    • Curve-hugging fit
    • Coated, faux leather fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06401-1347

    Category Name: Night Out

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tied With Lace Crop Top
    This lace tie front crop top is simply irresistible! It features long flared sleeves, a V neckline created by a tie front, a cropped hem, and eyelash lace trim. The sheer lace top showcases a floral pattern and offers moderate stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06204-4784

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic And Sophisticated Trench

    Turn heads with this chic and sophisticated trench! It features a drape front with a flat lapel collar, long sleeves, an elastic banded back with a tie front, and a relaxed, flowy fit. The trench is composed of a sheer woven fabric with no stretch.

    Style Number/Barcode: 06204-4771

    Category Name: Night Out

    Price: $10.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Setting The Trend Cropped Moto
    Set the bar in this chic ivory moto! The ivory jacket features a flat collar, a zippered front, two side faux pocket accents, fitted long sleeves with zippered cuffs and a cropped hem. Jacket is composed of a denim-like fabric that offers a form hugging fit with minimal stretch. Includes a smooth knit lining

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06204-4765

    Category Name: Night Out

    Price: $16.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • That's Our Moto Faux Suede Jacket

    You know what they say, dress like you're going somewhere! This taupe faux suede moto jacket is a perfect piece to take. It features a fold over collar, long fitted sleeves, lattice strap details on the sides, a zip up front, and a slim fit throughout. 

    Model is 5'6.5 with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-4695

    Category Name: Night Out

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Prowl Tie Front Top

    You've been on the prowl for a new fierce top, and this one will make you look so fab! It features long, flowy bell sleeves, an adorable tie front closure, and a cropped hem. The leopard print top is composed of a sheer, chiffon fabric with no stretch.

    Style Number/Barcode: 06204-4596

    Category Name: Night Out

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Making Moves Moto Jacket

    Make your next stylish move in this moto jacket! It features a flat collar with stud detailing, an asymmetrical zip front, zippered pockets and a fitted look. Pair this jacket with a basic bodysuit and stylish mini skirt for an edgy-chic look.

    Fit & Features

    • Flat collar with stud detailing
    • Asymmetrical zip front
    • Zippered pockets
    • Long sleeves with zippered accents
    • Form-fitting style
    • Smooth faux suede fabric
    • Minimal stretch

    Style Number/Barcode: 06204-4699

    Category Name: Night Out

    Price: $21.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Baby, I Want Moto Jacket

    Play for keeps in a moto jacket that lets them know what's up. The moto jacket features a notch collar, an asymmetrical zipper front, zippered accents at the bodice, and long sleeves with trendy shoulder tabs. Complete your irresistible look with a basic bodysuit and dark wash denim jeans. 

    Fit & Features

    • Notch collar neckline
    • Asymmetrical zipper front
    • Long sleeves, trendy shoulder tabs
    • Lightly padded shoulders
    • Additional zipper accents
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06204-4455

    Category Name: Night Out

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lattice Faux Suede Moto Jacket

    Suit up in faux suede to get those cool girl vibes this season! This moto jacket features a flat collar with decorative buttons, an asymmetric zipper front, a small zipper pocket front, long sleeves, and front lattice details. The all-over faux suede fabric offers a soft-to-the-touch feel with a natural fit with minimal stretch. Pair this jacket with black skinny jeans and strappy heels.

    Fit & Features

    • Flat collar with button detailing
    • Asymmetric zip front
    • Zippered pocket
    • Long sleeves
    • Lattice details
    • Faux suede fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-3721

    Category Name: Night Out

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ponte In Your Direction Blazer

    Lead the way in this chic blazer. It features a notch collar and open front, slight shoulder padding, three-quarter sleeves with a snap button detail and accent pockets. Ponte fabric offers minimal stretch.

    Style Number/Barcode: 06204-0115

    Category Name: Night Out

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Zipped Jacket

    It's all in the zipper details! This moto jacket is a must for a chic and sleek vibe. Layer this jacket for a night out with the squad. The jacket features an asymmetrical zipper front, small zippered pockets, zipper details on the shoulder, a cropped, form-hugging fit, and is composed of faux leather fabric. Complete your look with high waist denim jeans and sleek hoops. 

    Fit & Features

    • Asymmetrical zip front
    • Zipper details along the shoulders
    • Small zipper pockets
    • Cropped silhouette, form-hugging fit
    • Faux leather fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06204-3077

    Category Name: Night Out

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Biker Chic Crop Jacket

    Change gears in a cropped jacket and add a little biker chic-ness to your look! Create an edgy look in this biker moto jacket that features an asymmetrical zipper front with a lapel collar, snap button accents, and an adjustable waist belt.

    Fit & Features

    • Faux leather fabric with no stretch, smooth lining
    • Lapel collar, asymmetrical zippered front
    • Long sleeves with zippered accents
    • Zipper and snap button accents
    • Adjustable waist belt
    • Runs true to size

    Style Number/Barcode: 06204-2669

    Category Name: Night Out

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making The Rules Boyfriend Blazer

    Take charge and make your own rules in this statement blazer!

    Fit & Features

    • Flat collar
    • Slight shoulder padding
    • Long roll up sleeves
    • Two faux front pockets
    • Oversized boyfriend fit | Drape open front
    • Lined textured woven fabric
    • Relaxed fit | Minimal stretch

    Ivory: Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0114

    Category Name: Night Out

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Baddie Babe Moto Jacket
    You're just a baddie with a chic sense of style! This black moto jacket features an asymmetrical zipper front, long sleeves, a zippered pocket, an adjustable belted hem and rose gold hued metal accents. Moto is composed of a lined  faux leather fabric that offers a form hugging fit with a slight stretch.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0049

    Category Name: Night Out

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Faux In Love With Suede Jacket
    Fall in love with this chic and sleek faux suede moto jacket! It features a collar with silver faux button details, buttoned shoulders, long sleeves with zipper accents, an asymmetrical zip front, zippered pockets on the front, and a belted waist with a silver buckle and grommets. The black jacket is composed of a smooth faux suede fabric with a woven lining.

    Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0011

    Category Name: Night Out

    Price: $15.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Laced In Elegance Cardigan

    Keep it poised and elegant in lace! This black cardigan features a V neckline, a multi button down front, long sleeves and a cropped hem. Cardigan is composed of an unlined floral lace fabric that offers a relaxed fit with minimal stretch. 

    Style Number/Barcode: 06202-1128

    Category Name: Night Out

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Caught In A Mesh Top
    Get caught up in this hot mesh of a top! This black, crop top has a flattering V neckline paired with a tie front, knot closure and long, narrow sleeves. The crop top is composed of a sheer, unlined mesh that offers plenty of stretch.

    Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.

    Style Number/Barcode: 06202-1098

    Category Name: Night Out

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Show Em' Who's Boss Bomber

    Show em' who's boss in this commanding camo bomber! The jacket features a drawstring hood, long sleeves with cinched cuffs, a complete zip front, front pockets, and an elastic banded hem. Pair this trendy jacket with a basic crop top and biker shorts for a casual-chic look.

    Fit & Features

    • Drawstring hood
    • Long sleeves
    • Zip front
    • Front pockets
    • Elastic banded hem
    • Sheer mesh fabric with moderate stretch
    • Mesh and nylon hood and partial nylon back

    Style Number/Barcode: 06202-1087

    Category Name: Night Out

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut To The Chase Bandage Dress

    Let's cut to the chase - this little black dress couldn't get any sultrier! It features a sleeveless bodice, spaghetti straps, a square neckline, bold and sexy side cut outs with bar accents, and an exposed back gold zipper and hook and eye closure. The dress is composed of a bandage knit fabric that offers a curve hugging fit and plenty of stretch.

    Style Number/Barcode: 06005-6240

    Category Name: Night Out

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Social Butterfly Lace Crop Top
    Show off that charisma in this adorable white crop top! It features an all over lace with lined cups, a deep V neckline with hook and eye closures, scalloped trim and adjustable straps.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-9876

    Category Name: Night Out

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ravishing Lace Bodysuit
    Nothing says ravishing like risque lace! The sleeveless bodysuit has an underwire bust paired with adjustable, elastic straps and a scoop back that features an additional strap detail. The cheeky bodysuit is composed of a sheer, unlined lace and mesh fabric, detailed with black piping and closes with a hook and eye bottom.

    Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.

    Style Number/Barcode: 06003-9890

    Category Name: Night Out

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortlessly Embellished Crop Top
    Create an effortless look with beyond gorg embellishments in this sheer mesh crop top! It features a crew neckline, short sleeves, and a cropped hem. The black top is adorned with pretty pearls and rhinestones. Top offers moderate stretch. Undergarment not included.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06003-9888

    Category Name: Night Out

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rhinestone Beauty Lace Bustier
    Draw all eyes on you as you dazzle in this statement making bustier! It features a sweetheart bust, unlined cups with underwire, adjustable narrow straps and a wired V inset. Bustier is composed of an unlined sheer floral lace fabric adorned with mini rhinestones throughout. Garment offers a form hugging fit with minimal stretch and includes a multi row fish hook closure. 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-9867

    Category Name: Night Out

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Stuff Banded Crop Top
    A little sweet, a little naughty. This black crop top features a daring strapless sweetheart neckline, a back zipper and a band hemline. Top is composed of a knit fabric with moderate stretch.

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-9877

    Category Name: Night Out

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance