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.

  • High Waist Tweed Knit Mini Skirt

    Keep it trendy in a high waist mini skirt that slays. The skirt features a high rise waist, a mini side slit and composed of a tweed knit fabric. Complete look with a ribbed crop top. 

    Fit & Features

    • High rise waist
    • Mini side slit
    • Tweed knit fabric
    • Form hugging fit

    Style Number/Barcode: 06401-0258

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay In Basics Ribbed Knit Mini Dress

    Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties. 

    Fit & Features

    • Mock neck
    • Long sleeves
    • Rounded mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06005-0852

    Category Name: Night Out

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flocked Floral Mesh Bodysuit

    This flocked floral mesh bodysuit would be perfect for a date night out with bae! It features long fitted sleeves, a form-fitting style, a sheer mesh fabric that offers plenty of stretch, and has an allover velvet flocked floral print. Pair this bodysuit with a faux leather mini skirt and thigh high boots.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Thong bottom with dual snap button closures
    • Form-hugging fit
    • Sheer mesh fabric with plenty of stretch
    • Allover velvet flocked floral print

    Style Number/Barcode: 06001-2947

    Category Name: Night Out

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Patent Pointed-Toe Lucite Block Heel Booties

    Show off a chic new look in these stunning patent pointed-toe booties! They feature a trendy clear lucite block heel and a sleek patent finish. Wear with your fave crop top and mom jeans to amp up your casual look.

    Fit & Features

    • Pointed-toe
    • Inner zipper closure
    • Lucite block heel
    • Patent material

    Style Number/Barcode: 07403-0385

    Category Name: Night Out

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Clearly On Trend Block Heels

    Clearly these buckle detail block heels are on trend! They feature a chic clear toe strap and a stylish buckle accent. Pair these heels with distressed denim to elevate an everyday casual look.

    Fit & Features

    • Open almond toe
    • Clear PVC toe strap
    • Adjustable around the ankle strap with buckle detail
    • Closed back
    • Block heel
    • Faux nubuck material

    Style Number/Barcode: 07401-2440

    Category Name: Night Out

    Price: $7.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Level Up Platform Block Heel Booties

    Level up your look in these chic block heel booties! Featuring a stylish platform and a sleek block heel, these booties are perfect for your next party. Simply pair them with a LBD and stunning statement earrings for a gorgeous look.

    Fit & Features

    • Almond toe
    • Platform
    • Thin block heel
    • Dual zipper detailing
    • Faux nubuck material

    Style Number/Barcode: 07403-0380

    Category Name: Night Out

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Viva La Velvet Biker Shorts

    Live it up in velvet biker shorts to glam up any outfit! Style with a cute crop top or oversize tee-shirt for a look that's ready to go! The biker shorts feature a high rise waist, a mid-thigh length, and composed of luxe velvet fabric. 

    Fit & Features

    • High rise waist
    • Mid-thigh length
    • Velvet fabric
    • Form hugging fit

    Style Number/Barcode: 06503-0184

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry And Stunning Snake Print Mini Skirt

    Look ever so sultry and stunning in this on-trend snake print mini skirt! It features a flattering high rise waist and an overall form-hugging fit to enhance your curves. Pair this skirt with trendy clear mules for your next night out with the girls.

    Shop Matching Top: Sultry And Stunning Snake Print Crop Top

    Fit & Features

    • High rise waist
    • Short, form-fitting style
    • Allover snake print
    • Mesh fabric

    Style Number/Barcode: 06501-0310

    Category Name: Night Out

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Style Faux Nubuck Block Heels

    Get wrapped in style with these chic heels that dress up all your best outfits! The heels feature an open back, wrap-around straps, an open square toe, a wide strap over the toe, and a narrow block heel. Complete look with a wrap mini dress and laritat necklace. 

    Fit & Features

    • Open back
    • Single strap over the back of the ankle
    • Wrap-around straps
    • Open square toe
    • Wide strap over the toe
    • Narrow block heel 
    • Faux nubuck material  

     

    Please be advised that these heels run small, purchase one size up. 

    Style Number/Barcode: 07401-2438

    Category Name: Night Out

    Price: $16.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed and Fierce Faux Nubuck Block Heels

    Keep it fierce in heels that let you unleash your inner fashionista. The heels feature an adjustable ankle strap, a trendy narrow block heel, an open square toe with a single strap over the toe. Complete your trendsetting look with a bodycon dress and a cropped blazer. 

    Fit & Features

    • Adjustable ankle strap
    • Closed-back 
    • Open square toe
    • Single strap over the toe
    • Narrow block heel 
    • Faux Nubuck material 
    • Available in Leopard print and Natural 

    Style Number/Barcode: 07401-2442

    Category Name: Night Out

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe Velvet High Rise Joggers

    Showcase a luxe look at your holiday party in these velvet high rise joggers! They feature a high rise banded waist with a tie front, side pockets, and a relaxed fit through the legs with a banded jogger hem. Pair these bottoms with a chic cropped blouse and your fave hoop earrings.

    Fit & Features

    • High rise banded waist
    • Tie front
    • Side pockets
    • Relaxed fit through the legs
    • Banded jogger hem
    • Ribbed velvet fabric

    Style Number/Barcode: 06502-0469

    Category Name: Night Out

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Fab Knee High Stiletto Heeled Boots

    You'll be feelin' oh-so-fab in these chic stiletto heeled boots! They feature a knee high design with a croc embossed print and a faux leather material. Pair these sleek boots with dark wash skinny jeans for a must-have fall look.

    Fit & Features

    • Knee high design
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux leather material
    • Croc embossed print

    Style Number/Barcode: 07402-0203

    Category Name: Night Out

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry And Stunning Snake Print Crop Top

    Look ever so sultry and stunning in this on-trend snake print crop top! It features a mock neckline and an overall form-hugging fit to enhance your curves. Pair this top with trendy clear mules for your next night out with the girls.

    Shop Matching Bottoms: Sultry And Stunning Snake Print Mini Skirt

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Cropped
    • Front ruched detailing with ties that close at back
    • Allover snake print
    • Mesh fabric

    Style Number/Barcode: 06001-2943

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Edgy Block Heel Booties

    Get an effortlessly edgy look in these faux nubuck block heel booties! They feature an ankle-high design with a chunky lug sole and a tall, sturdy block heel. Pair these booties with dark wash skinny jeans and an oversized sweater for major fall vibes.

    Fit & Features

    • Ankle-high design
    • Round toe
    • Inner zipper closure
    • Lug sole
    • Block heel
    • Faux nubuck material
    • Partial elastic detail at ankle

    Style Number/Barcode: 07403-0386

    Category Name: Night Out

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Chic Stiletto Booties

    Stylish and oh-so-chic, these stiletto booties are a must-have for a night out with the girls! They feature an open toe design with a sexy stiletto heel. Pair these booties with a curve-hugging bodycon dress for a gorgeous look from head to toe.

    Fit & Features

    • Open toe
    • Dual front cut outs
    • Sleek stiletto heel
    • Back zipper closure
    • Above the ankle height
    • Faux nubuck material

    Style Number/Barcode: 07403-0382

    Category Name: Night Out

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Trendsetter Zebra Print Stiletto Heels

    Get ready to strut in these zebra print stilettos and you'll be the major trendsetter of your squad! Featuring a wrap-around ankle design and a bold zebra print, pair these heels with a simple yet stunning mini dress for your next night out.

    Fit & Features

    • Open almond toe with a toe strap
    • Strappy design with double adjustable ankle straps
    • Open back
    • Sleek stiletto heel
    • Faux leather material 
    • Zebra print

     

    Please be advised that these heels run small. Fit model recommends one size up.

    Style Number/Barcode: 07401-2439

    Category Name: Night Out

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Twist Back Ribbed Knit Midi Sweater Dress

    Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Open back with twist back detail
    • Mid-length silhouette
    • Form-hugging fit
    • Ribbed sweater knit fabric

    Style Number/Barcode: 06005-0846

    Category Name: Night Out

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flutter Some Hearts Mesh Crop Top

    You'll be sure to flutter some hearts in this chic mesh crop top! It features a high crew neckline, long sleeves with puff shoulders, a cropped, fitted style, and is composed of a sheer mesh fabric with all-over butterfly appliques. Pair this top with high rise denim to dress it down or a faux leather mini skirt for a night out.

    Fit & Features

    • High crew neckline
    • Long sleeves with puff shoulders
    • Complete back zipper and hook and eye closure
    • Cropped, fitted style
    • Sheer mesh fabric
    • All-over butterfly appliques
    • No stretch

    Style Number/Barcode: 06003-1123

    Category Name: Night Out

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Cozy Vibes Duster

    Get major cozy vibes in this adorable flowy duster! It features long fitted sleeves, a mid-length flowy fit and a textured knit fabric. Complete your loungewear look with chic slides for the ultimate stay at home 'fit.

    Shop Matching Top: Major Cozy Vibes Cropped Tank

    Shop Matching Bottoms: Major Cozy Vibes Wide Leg Pants

    Fit & Features

    • Long fitted sleeves
    • Mid-length hem
    • Flowy, relaxed fit
    • Textured knit fabric

    Style Number/Barcode: 06202-0117

    Category Name: Night Out

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Cozy Vibes Cropped Tank

    Get major cozy vibes in this adorable cropped tank! It features a flattering scoop neckline, a majorly cropped hem and a textured knit fabric. Complete your loungewear look with chic slides for the ultimate stay at home 'fit.

    Shop Matching Duster: Major Cozy Vibes Duster

    Shop Matching Bottoms: Major Cozy Vibes Wide Leg Pants

    Fit & Features

    • Tank-like shoulder straps
    • Scoop neckline
    • Cropped hem
    • Form-hugging fit
    • Textured knit fabric

    Style Number/Barcode: 06001-2938

    Category Name: Night Out

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fashionista Moment Mini Croc Crossbody Purse

    This purse is for the fashionistas out there looking to make a chic statement! Perfect for a brunch date or fab night out, this mini purse is the one! The purse features top handles, a fold-over closure, and a mini square design. Complete your look with a sleek bodysuit and high waist jeans. 

    Fit & Features

    • Mini square design
    • Fold-over closure
    • Double handles
    • Detachable shoulder strap
    • Croc-embossed design 
    • Faux leather material 

    Style Number/Barcode: 07201-0043

    Category Name: Night Out

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold and Fierce Leopard Print Crop Top

    Strike a bold look in this crop top that slays! The top features a bold leopard print, a high round neckline, shoulder pads, and a cropped hem. Complete your look with high waist leggings. 

    Fit & Features

    • High round neckline
    • Sleeveless
    • Shoulder pads
    • Leopard print
    • Cropped hem
    • Brushed woven fabric with moderate stretch

    Style Number/Barcode: 06003-1121

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Reign N' Shine Rhinestone Bustier

    Reign the night with a sparkling bustier that puts you in the spotlight! The bustier features a sleeveless sweetheart neckline, padded push-up cups, removable and adjustable spaghetti straps, a dazzling sequin and rhinestone embellished bodice, a sheer mesh insert under the bust with contrast flexible boning, a cropped hem, and back hook and eye closures. Complete your party look with a high waist mini skirt.

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Padded push-up cups 
    • Removable and adjustable spaghetti straps
    • Sequin and rhinestone embellishments
    • Sheer mesh insert under the bust, contrast flexible boning
    • Cropped hem, back hook and eye closures
    • Form-hugging fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1125

    Category Name: Night Out

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chrome Cutie Block Heels

    Keep it chic in chrome heels that will create head-turning looks! The heels feature a chrome finish, an open almond toe with a single strap over the toe and a sturdy block heel. Complete your outfit with a stunning formal dress. 

    Fit & Features

    • Narrow adjustable ankle strap
    • Open almond toe with a single strap over the toe
    • Closed-back 
    • Block heel
    • Chrome finish 

    Style Number/Barcode: 07401-2433

    Category Name: Night Out

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale