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.

  • Chic Chiffon Square Neck Top

    Trendy chic is your go-to. This square neck top is a definite add to cart!

    Fit & Features

    • Square neckline
    • Long sheer chiffon sleeves | Triple button detailing
    • Stretchy smocked back
    • Woven fabric | Moderate stretch
     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 06003-0441

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It A Secret Mini Skirt

    You'll be lookin' so stunning in this sequin mini skirt, your whole squad will want to know your secret! Don't forget pair it with the matching crop top.

    Shop Matching Top: Keep It A Secret Crop Top

    Fit & Features

    • High rise elastic banded waist
    • Short, curve hugging fit
    • Velvet knit fabric with all over sequins
    • Moderate stretch

    Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.  

    Style Number/Barcode: 06501-0141

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Key Moment Knit Bodysuit

    Have a major key moment in this trendy cut out bodysuit! Paired with a faux leather mini skirt and some edgy booties, you'll be ready for a night out!

    Fit & Features

    • Mock neckline
    • Side keyhole cut out detailing by the neck
    • Long fitted sleeves
    • Thong bottom | Dual snap button closures
    • Ribbed knit fabric
    • Form hugging fit | Plenty of stretch

    Style Number/Barcode: 06001-2555

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep On Dancing Chrome Low Wedges

    Comfortable, but make it glam! These chrome wedges are the best to style with a long dress! They will keep you comfortable while you dance the night away, and obvs accent your look in the best way possible!

    • Open almond toe
    • Single band
    • Ankle strap 
    • Adjustable pin buckle closure
    • Low wedge heel
    • Silver chrome finish

    Style Number/Barcode: 07406-0078

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tear Drop Rhinestone Collar and Duster Earrings Set

    Dazzle with a collar necklace that stuns! The set features a v-sha[ed collar with a row of rhinestones, dark-hued teardrop gems, and larger rhinestones. The matching duster earrings feature rhinestones and teardrop gems. Complete your outfit with a sweeping formal dress and sleek stiletto heels

    Fit & Features

    • V-shaped collar
    • Rhinestones
    • Dark-hued teardrop gems
    • Matching duster earrings 

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged

     

    Style Number/Barcode: 07002-0523

    Category Name: Night Out

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Diva Chunky Platform Block Heels

    Yes babe, you'll be a total fashion diva in these trendy block heels! They feature a chunky platform with a sturdy tall block heel. Pair these with a flirty curve-hugging midi dress for an elevated look.

    Fit & Features

    • Open toe
    • Thin toe strap
    • Thin around then ankle strap
    • Closed-back with zipper closure
    • Chunky platform
    • Tall block heel

    Style Number/Barcode: 07401-2319

    Category Name: Night Out

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild and Glam Faux Leather Leopard Purse

    Keep it wild and glam in a purse that stuns! The purse features a leopard print, a top handle, a small rectangular body, and an envelope fold-over design with a fasten closure. Complete look with high waist joggers

    Fit & Features

    • Top handle
    • Leopard print
    • Small rectangular body
    • Envelope design with a fasten closure
    • Faux leather material
    • Woven interior with a single pocket
    • Removable chain shoulder strap

    Style Number/Barcode: 07203-0443

    Category Name: Night Out

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Babe Ruched Midi Dress

    Yes babe, show off your gorgeous curves in this figure-flattering midi dress. It features thick and thin spaghetti straps, a cowl neckline, ruched detailing, and a mid-length, form-hugging fit. The knit fabric offers plenty of stretch for comfortable wear. Pair this dress with clear mules and a sleek clutch.

    Fit & Features

    • Thick and thin spaghetti straps
    • Cowl neckline
    • Square back
    • Ruched
    • Mid-length, form-fitting style
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0930

    Category Name: Night Out

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring Sleek O-Ring Cutout Bodycon Mini Dress

    Dare to showcase a sultry allure in this smooth knit mini dress designed with a plunging V-neckline, a sleek asymmetric metal O-ring accent at the bust, and dual side cutouts that lead to a bold open lower back. The ruching on the bodycon silhouette will flaunt your stunning figure.

    Fit & Features

    • Smooth double-lined knit fabric, plenty of stretch
    • Plunge V-neckline, padded bust, asymmetric metal O-ring accent
    • Spaghetti straps
    • Dual side cutouts leading to open lower back
    • Ruched detailing
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5856

    Category Name: Night Out

    Price: $28.00 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • Keeping Knit Sultry Long Sleeve Mini Dress

    Keep it sultry in a dress that showcases curves in all the right places! The dress features a square neckline, ruched long sleeves, and mini length silhouette. Complete your look with clear mules and hoops for the perfect night out look. 

    Fit & Features

    • Square neckline
    • Ruched long sleeves
    • Mini length silhouette
    • Smooth knit fabric
    • Form-hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05103-3780

    Category Name: Night Out

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Step Up Snake Print Bodysuit

    Step up your style game with a sassy snake print bodysuit. The bodysuit features a mock neck, short sleeves, and a snake print. The bodysuit is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete your look with a high waist mini skirt

    Fit & Features

    • Mock neck 
    • Short sleeves
    • Snake print
    • Form hugging fit, moderate stretch 
    • Brushed knit fabric 
    • Dual snap button closure 
    • Runs true to size

    Style Number/Barcode: 06001-3142

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Fierce Snake Print Mini Dress

    Keep your look forever fierce in this trendy snake print mini dress. It features a sleeveless square neckline, bungee spaghetti straps, and a short, form-fitting silhouette to hug your curves. Style this dress with clear heels for a night out with the girls.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Mini-length, form-hugging fit
    • Snake print
    • Knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-3928

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Drama Textured Door Knockers

    For the diva that is so extra, these door knockers are a must! The earrings feature a door knocker design and a textured finish that reflects a dazzling shine. Complete your look with a sleek bodycon dress to create a head-turning look.

    Fit & Features

    • Textured disc on post
    • Door knocker design
    • Textured finish
    • Post-back closure

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0961

    Category Name: Night Out

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Thing Zebra Halter Top

    Tap into your wild side with a halter top that makes a fierce impression! The top features a trendy zebra print, a halter neck, a drawstring tie front, and a cropped hem. The top is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching midi skirt.

    Shop Matching Midi Skirt: Wild Thing Zebra Midi Skirt

    Fit & Features

    • Zebra print
    • Halter neck 
    • Drawstring tie front
    • Cropped hem 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-3797

    Category Name: Night Out

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Mood Leopard Print Midi Skirt

    Showcase a sassy mood in this trendy leopard print midi skirt! It features a flattering high-rise waist, a fitted midi-length silhouette, and a chic high side slit for a sultry vibe. Style with a neutral crop top and strappy heels.

    Fit & Features

    • High-rise elasticized waist
    • Form-hugging midi-length silhouette
    • High side slit
    • Leopard print
    • Soft brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0672

    Category Name: Night Out

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stay Trendy Split Hem Pants

    Keep your look trendy and chic with these high-rise knit pants. They feature an elasticized waist for comfortable wear, vertical seams running down the front, a flared-leg silhouette, and a front split hem design. Style with a cropped blouse and clear heels for happy hour.

    Fit & Features

    • High-rise elasticized waist
    • Vertical seams running down the front
    • Flared-leg silhouette
    • Front split hem design
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-1621

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Best Of Times Scoop Neck Midi Dress

    Have the best of times with the girls in this sleek and sultry midi dress you'll love dressing up! It features a sleeveless scoop neck with spaghetti straps and a bodycon silhouette composed of double-lined slinky knit fabric. Complete the look in a chic jacket and heels.

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Double-lined slinky knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2100

    Category Name: Night Out

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make It Chic Chunky Chain Necklace

    Make any of your casual 'fits chic with this chunky chain necklace! It features a collar-length oval-shaped chain-link design. Style with sleek hoops for a trendy look.

    Fit & Features

    • Chunky oval-shaped chain-link design
    • Collar-length
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1635

    Category Name: Night Out

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shine Attitude Slit Mini Skort

    Shine bright with attitude in this trendy mini skort! Perfect for creating a going-out look, it features a sleek high-rise waist, a front skirt overlay with a slit, a form-hugging fit, and a shorts lining. The woven fabric has a stylish sheen effect. Complete the outfit in a lace bustier, heels, and a mini handbag!

    Fit & Features

    • High-rise waist
    • Front skirt overlay, slit accent
    • Form-hugging fit
    • Shorts lining
    • Woven fabric, sheen effect, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0348

    Category Name: Night Out

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Starstruck Velvet Flocked Mesh Crop Top

    Leave them starstruck by your trendy style in this velvet flocked mesh crop top! It features a mock neckline, long fitted sleeves, a fitted cropped hem, lettuce edge hems, and a velvet flocked star pattern on the stretchy sheer mesh fabric. Style this top with a lacy bralette and faux leather pants for a concert.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Fitted cropped hem
    • Lettuce edge hems
    • Star print flocked velvet pattern
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-5096

    Category Name: Night Out

    Price: $11.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fine High-Rise Lace Flare Pants

    Gorgeous lace romances these flattering high-rise pants! They feature a hip-hugging fit, a short knit stretchy lining, a flared hem, and a semi-sheer lace design. Complete the look in a cute sleeveless tank top for a festival or concert!

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Flared hem
    • Semi-sheer lace design, short knit stretchy lining
    • Runs true to size

    Style Number/Barcode: 06502-2452

    Category Name: Night Out

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Desire Rhinestone Heart-Shaped Crop Top

    This rhinestone crop top's sparkling details will leave you falling head over heels for the glamour! The crepe fabric offers a moderate stretch. The crop top features a sleeveless sweetheart neckline for a sweet allure with adjustable spaghetti straps for a customized fit. The adorable heart-shaped front design is accented with a rhinestone trim for a gorgeous glitzy vibe. The top's fitted ultra-cropped hem will create a snatched silhouette. Style with a mini skirt and mules for a party!

    Fit & Features

    • Crepe knit fabric with front lining, minimal stretch
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Back zipper, hook and eye closure
    • Heart-shaped front design with rhinestone trim
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5041

    Category Name: Night Out

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Country Era Faux Leather Under-The-Knee Cowboy Boots

    Enter your country-girl era with these totally fab cowboy boots! Made with sleek faux leather material, these under-the-knee boots feature a pointed toe, a sturdy block heel for comfortable wear, a western-inspired stitched design, and pull tabs for effortless on-and-off styling. Pair with a flirty short dress and hoop earrings for a concert or party!

    Fit & Features

    • 3" Block heel
    • 8" Leg opening and a 11" shaft height
    • Under-the-knee shaft
    • Faux leather upper
    • Pointed toe
    • Pull tabs
    • Runs true to size

    Style Number/Barcode: 07402-1012

    Category Name: Night Out

    Price: $11.97 $50.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Majorly Fab Lace-Up Faux Leather Shorts

    Amp up your going-out looks with these majorly fab lace-up faux leather shorts. They feature a high-rise waist for a snatched silhouette, a lace-up front design to add some allure, pleated accents on the front and back, and a cheeky form-hugging fit. Style with a bodysuit and sneakers for a casual-chic night-out vibe!

    Fit & Features

    • Coated faux leather fabric, moderate stretch
    • High waist
    • Cheeky form-hugging fit
    • Lattice front design
    • Pleating
    • Back zipper with hook and eye closure
    • Runs true to size

    Style Number/Barcode: 06403-0474

    Category Name: Night Out

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free