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.

  • Stunning Sophistication Satin Trench Dress

    Keep it stunning with a luxe statement! This trench dress features a plunging V neckline, fitted long sleeves, a zippered front, a tie waist belt and a flared skater silhouette. Dress is composed of a satin-like fabric that offers a form hugging fit with minimal stretch.  

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

    Style Number/Barcode: 06204-0116

    Category Name: Night Out

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Print Cropped Burnout Bustier

    Keep it fierce in a bustier that slays for your next night out! The bustier features a burnout leopard print, adjustable spaghetti straps, a sweetheart neckline, and a cropped hem. Complete look with high waist black liquid pants.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Burnout leopard print
    • Sweetheart neckline
    • Cropped hem 

    Style Number/Barcode: 06003-1072

    Category Name: Night Out

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Sleek Bandage Pencil Skirt

    Keep your look so sleek with a pencil skirt that is perfect for stylish workwear outfits! The skirt features a high rise waist, and an above-the-knee length, and composed of a bandage knit fabric. Complete look with a blouse and mules. 

    Fit & Features

    • High rise waist
    • Above the knee length 
    • Bandage knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06501-0495

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Sassy Stiletto Heels

    These sleek and sassy stilettos will take your night-out looks to the next level! They feature an open square-shaped toe, dual thin straps, a lace-up design that goes up the leg, and a stiletto heel. Style these shoes with a faux leather clutch.

    Fit & Features

    • Open square-shaped toe
    • Dual straps
    • Lace-up design
    • Stiletto heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-3347

    Category Name: Night Out

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Drama Platform Booties

    You'll bring all the drama in these chic platform booties. They feature an above the ankle fit, an almond-shaped toe, a trendy lace-up design, a tall platform, and a block heel. Complete the look with sleek hoop earrings.

    Fit & Features

    • Above the ankle fit
    • Almond-shaped toe
    • Lace-up front design
    • Platform
    • Block heel
    • Faux nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1333

    Category Name: Night Out

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Wraps Envelope Side Tie Mini Skirt

    The perfect chic wrap to add style to your look. This mini skirt features a high-rise waist, envelope side tie, composed of faux leather fabric with a moderate stretch. Complete the look with peep-toe booties.

    Fit & Features

    • High-rise waist
    • Envelope side tie
    • Mini length hem
    • Faux leather fabric, moderate stretch
    • Fits true to size 

    Style Number/Barcode: 06501-0565

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Sleek Bodycon Mini Skirt

    Amp up your night-out looks with this classic and sleek faux leather mini skirt. It features a high-rise waist, vertical seam detailing down the front, and a short, curve-hugging, bodycon silhouette. Style this skirt with strappy stilettos.

    Fit & Features

    • High-rise waist
    • Vertical seam details
    • Back zipper closure
    • Mini-length, form-fitting silhouette
    • Coated faux leather fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0452

    Category Name: Night Out

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Shine Rhinestone Braid Belt

    It's your time to shine and this glitzy rhinestone belt is the perfect accessory to dress up your formal look! It features a braided design with a lobster clasp closure. Complete the look in a classy satin dress. 

    Fit & Features

    • Braided design
    • Rhinestone insets
    • Lobster clasp closure

    Style Number/Barcode: 07301-0438

    Category Name: Night Out

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cubic Zirconia Tennis Bracelet

    This cubic zirconia tennis bracelet is sure to add some sparkle to your outfits! It features a single row of cubic zirconia stones that will glam up your outfit of the day. Style with a midi dress, a chic blazer, and heeled booties.

    Fit & Features

    • Single row
    • Square-shaped cubic zirconia stones
    • Clasp closure

    Style Number/Barcode: 07003-2311

    Category Name: Night Out

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Spot To Go Halter Jumpsuit

    You may be at the hottest spot in town but you'll be the one raising the heat in this sleeveless halter jumpsuit featuring a front keyhole cutout, tie-back neck closure, high-rise waist, wide-leg silhouette, and a racerback design with a cutout. Complete the look in statement earrings and a clutch.

    Fit & Features

    • Sleeveless, halter, tie-back neck closure
    • Front keyhole cutout
    • Racerback design with cutout
    • High-rise waist
    • Wide-leg silhouette
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06502-1079

    Category Name: Night Out

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 90s Reboot Faux Leather Mini Skirt

    Look and feel like a total 90s babe in this faux leather mini skirt featuring a high-rise waist, bodycon silhouette, a front button, hidden zipper closure, side pockets, and belt loop accents. Complete the look in a mesh top for a night out.

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Front button and hidden zipper closure
    • Side pockets, belt loop accents
    • Faux leather fabric
    • Fits true to size

    Style Number/Barcode: 06401-0478

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Futuristic Faux Leather Mini Skirt

    Chanel an out-of-this-world style in this faux leather mini skirt featuring a sleek high-rise waist, back zipper closure, side pleated seam, bodycon fit, and an asymmetrical wrap hem. Complete the look in a beaded bustier.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Side pleated seam
    • Bodycon silhouette
    • Asymmetrical wrap mini hem
    • Faux leather fabric, lining, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06401-0494

    Category Name: Night Out

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Showstop The Party Satin Rhinestone Mini Dress

    Dare to stand out in this show-stopping mini dress! Featuring a sleeveless sweetheart neckline, an eye-catching bust twist cutout, rhinestone-embellished straps, a bodycon silhouette, and beautiful side pleating - you'll turn heads everywhere you go! Get ready to discover your daring side and complete the look with platform heels for a night on the town.

    Fit & Features

    • Sleeveless sweetheart neckline, twist bust cutout
    • Rhinestone-embellished straps
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Side pleating, mini-length hem
    • Lined silky satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05103-5002

    Category Name: Night Out

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ombre Effect Rhinestone Lucite Block Heel Mules

    Unleash your chic sense of style in these block heel mules! Featuring a square toe, shimmering rhinestone ombre embellished strap, and clear PVC strap, these mules make a sparkling statement. Plus, the lucite block heel and faux leather footbed offer comfort and stability, while the metallic trim adds the perfect shimmer. Complete the look with a statement ring set for a dressy event or celebration!

    Fit & Features

    • Square toe
    • Rhinestone ombre embellished strap
    • Clear PVC strap
    • Lucite block heel
    • Faux leather footbed, metallic trim
    • Runs true to size

    Style Number/Barcode: 07401-4596

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Capture Your Sparkle Sequin Strapless Romper

    Capture your sparkle in this sequin romper perfect for having a glitzy night! It features a strapless sweetheart neckline with non-slip grip lining, a padded bust with a flirty knot tie accent, a fitted high-waist seam, and flowy short bottoms. Complete the look with a necklace for a birthday or holiday party!

    Fit & Features

    • Strapless sweetheart neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Padded bust, knot tie accent
    • Fitted high-waist seam
    • Flowy short-length bottoms
    • Sequin striped pattern, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 06403-0362

    Category Name: Night Out

    Price: $13.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sexy Sensation One-Shoulder Corset Bodycon Mini Dress

    A sexy mini dress features a one-shoulder neckline, a sheer fitted long sleeve, and a sheer corset bodice with trim. Flaunt your figure in the bodycon mini-length silhouette perfect for styling with heels. 

    Fit & Features

    • Crepe fabric, partial lining, moderate stretch
    • One-shoulder neckline
    • Sheer fitted long sleeve
    • Back zipper and hook-eye closure
    • Sheer corset bodice with trim
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5587

    Category Name: Night Out

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Strapless Cropped Bustier

    Flirt alert! Create a spicy night-out look with this cropped bustier. It features a strapless sweetheart neckline with non-slip grip lining, vertical seams with flexible boning inserts, front hook, and eye closures, a fitted, cropped hem, and is composed of a supportive bandage knit fabric for a snatched look. Complete your 'fit with a faux leather mini skirt and mules.

    Fit & Features

    • Strapless sweetheart neckline
    • Non-slip grip lining
    • Vertical seam detailing, flexible boning inserts
    • Front hook and eye closures
    • Fitted, cropped hem
    • Bandage knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4822

    Category Name: Night Out

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Club Nights Mesh Strappy Mini Dress

    This mesh mini dress is here for your next club night! It features a sleeveless V-neckline, sleek bungee spaghetti straps that create the strappy open-back design, a ruched bodycon silhouette, and a mini-length hem. The lined mesh fabric offers a moderate stretch. Style this mini-length dress with platform heels and earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Strappy open-back design
    • Ruched bodycon silhouette
    • Mini-length hem
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4921

    Category Name: Night Out

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Sweetheart Midi Dress

    Sweet but sexy, this denim midi dress was made for you! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, corset-style bodice, and a high-waist seam leading to the bodycon silhouette with a back slit accent. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Corset-style bodice, back zipper closure
    • High-waist seam, back slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4477

    Category Name: Night Out

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love In Lace Bustier
    Fall in love with lace with this gorgeous bustier top! It features a sleeveless bodice, a flattering underwire, sweetheart bust, adjustable spaghetti straps, a back hook and eye closure, and a pretty eyelash trim detail. The black top is composed of a sheer lace fabric with a form-fitting style.

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

    Style Number/Barcode: 06003-9772

    Category Name: Night Out

    Price: $9.94 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let The Party Begin Sequin Mini Dress

    Let the party commence! The qween has arrived! This dazzling party dress is designed with a mock halter neckline, a sleeveless bodice, and a form fitting silhouette. Dress is composed of a mesh material that showcases a scroll sequin pattern that reflects rose gold. Offering slight stretch, the dress features a full lining and a zipper closure at the back.

    Model is 5'9" with a 32" bust, 24.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0145

    Category Name: Night Out

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Caressa Sequin Evening Gown

    Special Occasion

    Introducing our Caressa! She features a v neckline, padded cups, and spaghetti straps that cross over at the back and lead to a lower back cut out and a zipper closure. She has a form fitting silhouette that leads to a mermaid floor length hem and a high thigh side slit. Caressa is composed of a lined knit material with a mesh overlay that is adorned in a geometric sequin pattern.

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0084

    Category Name: Night Out

    Price: $29.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Here For It Point Toe Stiletto Boots

    Over the knee boots are coming in full force, and we are here for it, are you!?

    • Over the knee fit
    • Pointed toe
    • Stiletto heel
    • Zipper closure
    • Faux suede

    Style Number/Barcode: 07402-0129

    Category Name: Night Out

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let Them Look Thigh High Boots

    Let them look, let them stare, because they are lovin' your style with those thigh high boots babe!

    • Thigh high fit
    • Almond toe
    • Low block heel
    • Lace back detailing
    • Inner zipper
    • Faux suede

    Style Number/Barcode: 07402-0118

    Category Name: Night Out

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free