Night Out

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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.

  • Cheers To You Off The Shoulder Mini Dress

    Don't be surprised by all the raised glasses when you stroll into the party in this adorable off-the-shoulder mini dress! It features a sweetheart neckline with non-slip grip lining, trendy puff short-sleeve cuffs, a padded and underwire bust, and ruched seams down the sides and back that flatter your curves along the bodycon silhouette. The dress is composed of a mesh fabric with a sewn-in knit lining. Complete the look with statement hoop earrings and heels.

    Fit & Features

    • Off-the-shoulder, sweetheart neckline, non-slip grip lining
    • Puff short-sleeve cuffs, back zipper and hook-eye closure
    • Padded and underwire bust
    • Ruched side and back seams
    • Bodycon silhouette, mini-length hem
    • Mesh fabric, sewn-in knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2571

    Category Name: Night Out

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gleaming With Glitz Ruffled Glitter Party Dress

    Gleam with all the glitz and glamour in this ruffled glitter party dress! It features a strapless straight-across neckline, all-over ruching, a mini-length ruffled hem, trendy cascading ruffled side trims, and a bodycon silhouette that will show off your curves. The glitzy sheer glitter mesh fabric includes a lining. Complete your gorgeous party look with rhinestone heels!

    Fit & Features

    • Strapless straight-across neckline
    • All-over ruching
    • Back zipper closure
    • Mini-length ruffled hem, cascading ruffled side trims
    • Bodycon silhouette
    • Sheer glitter mesh fabric, full-length lining
    • Runs true to size

    Style Number/Barcode: 05103-5149

    Category Name: Night Out

    Price: $9.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glam Bombshell Faux Pearl Mesh Bustier

    Show your glam bombshell side in this faux pearl mesh bustier perfect for modern brides, bachelorettes, or an evening out! Designed on soft mesh fabric, it features an off-the-shoulder sweetheart neckline, fitted sheer long sleeves, a satin built-in padded underwire bust, flexible boning inserts, faux pearl embellishments, and multiple back hook and eye closures. Complete the look in a flirty mini skirt.

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Sheer mesh fitted long sleeves
    • Satin built-in padded underwire bust
    • Flexible boning inserts, cropped hem
    • Faux pearl embellishments
    • Lined mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4983

    Category Name: Night Out

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Satin Sling-Back Stiletto Heels

    The satin stiletto heels feature a smooth satin material designed with an open square-shaped toe, a chic sling-back strap design, and a short stiletto heel for comfortable wear. Style with a sleek shoulder bag.

    Fit & Features

    • 2" Stiletto heel
    • Satin material
    • Open square toe
    • Toe strap
    • Sling-back strap design
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4913

    Category Name: Night Out

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Presently Chic Satin Bow Mini Dress

    You'll be presently chic in this satin mini dress for dressy birthday dinners or date nights! The dress features a sleeveless V-neckline, spaghetti straps, a statement bow across the bust, a bodycon silhouette, and a flirty slit accent on the hem. Complete the look in platform heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Statement bow across the bust
    • Bodycon silhouette
    • Slit accent, mini-length hem
    • Smooth satin fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05101-2412

    Category Name: Night Out

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iridescent Beauty Embellished Bra

    Get an iridescent glow with this beautifully bedazzled bra top! It features a sleeveless bodice, adjustable spaghetti straps, padded and molded cups, a square back with hook and eye closures, and a cropped hem. Top is composed of a knit fabric and is embellished with glimmering teardrop and round shaped multi-faceted gems. Complete your angelic Halloween costume with the coordinating pieces from our Halloween shop!

    Model is 5'9" with a 34" bust, 24" waist, and 34.5" hips. She is wearing a size small.

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

     

    Style Number/Barcode: 06003-0189

    Category Name: Night Out

    Price: $16.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fall Ready Faux Suede Mini Skirt
    Be totally fall ready with this must have mini skirt. It features a high rise waist, multi seam detailing dwon the front and back, a back zipper closure, and a short, form hugging fit. The techno faux suede fabric offers moderate stretch.

    Style Number/Barcode: 06501-0099

    Category Name: Night Out

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glam Moment Rhinestone Block Heels

    Have a major glam moment in these fabulous rhinestone block heels! They feature an open almond-shaped toe, a toe strap and ankle strap, a back zipper closure, a platform, and a tall block heel. The all-over rhinestone embellishment will make you sparkle with every step! Style these heels with a formal dress and a sleek clutch.

    Fit & Features

    • Open almond-shaped toe
    • Toe strap, ankle strap
    • Back zipper closure
    • Platform
    • Block heel
    • Rhinestones
    • Runs true to size

    Style Number/Barcode: 07401-2766

    Category Name: Night Out

    Price: $12.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Platform Block Heel Booties

    Step out and stun in these chic booties! They feature an almond-shaped peep toe, an ankle-high design, a back zipper closure, and a stacked block heel. Complete the look with a sleek clutch.

    Fit & Features

    • Almond-shaped peep toe
    • Ankle-high design
    • Back zipper closure
    • Stacked block heel
    • Faux nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1295

    Category Name: Night Out

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All This Love Cowl Halter Crop Top

    A sweet crop top with a sultry open back and cowl halter neckline that dresses up your favorite jeans.

    Fit & Features

    • Smooth knit stretchy fabric
    • Cowl halter neckline, spaghetti strap tie
    • Open back
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000087

    Category Name: Night Out

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Layers Plaid Sherpa Shacket

    Bundle up in the plaid sherpa jacket. It features button cuffed long sleeves, collar neckline, a four-pocket design, a button-down front, and an oversized fit. The cozy sherpa fabric offers a minimal stretch. Complete your look with booties.

    Fit & Features

    • Button cuffed long sleeves
    • Collar neckline
    • Button-down front
    • Four-pocket design
    • Oversized fit
    • Plaid sherpa fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-1167

    Category Name: Night Out

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trend Alert Faux Suede Stiletto Heels

    Stay on trend with heels that bring that stylish flair to your outfit! The heels feature a closed-back, an adjustable ankle strap, an open square toe with a strap over the toe, and a sleek stiletto heel. The heels are composed of a faux suede material. Complete look with a ruched midi dress and fake eyelashes

    Fit & Features

    • Closed-back 
    • Adjustable ankle strap 
    • Open square toe, strap over the toe
    • Stiletto heel
    • Faux suede material 
    • Runs true to size

    Style Number/Barcode: 07401-3476

    Category Name: Night Out

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Night Wrap Maxi Skirt

    Look sexy in this maxi skirt for your next all-nighter! It features a high-rise waist, wrap-twist front, and sultry slit. Composed of sleek knit fabric with a moderate stretch. Style with the matching top.

    Shop The Matching Top: All Night Plunge Halter Top

    Fit & Features

    • High-rise waist
    • Wrap twist
    • Front slit
    • Maxi length hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06501-0587

    Category Name: Night Out

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Ways Ruched High Slit Midi Skirt

    With this flirty midi skirt for celebrations or date night, you'll stun with the ruched detailing and high-cut side slit. Pair with the matching crop top to complete the look.

    Shop Matching Top: Flirty Ways Halter Lace Trim Crop Top

    Fit & Features

    • Stretchy smooth knit fabric with lining
    • High-rise waist
    • Ruching
    • Asymmetric high-side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000023

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Mini Dress

    You'll always look on point in this trendy ruched mini dress! It features a sleeveless square neckline, bungee straps, a high waist seam, side ruched detailing with adjustable drawstrings, and a short, curve-hugging fit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • High waist seam
    • Side ruching, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4472

    Category Name: Night Out

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trixie Strapless Faux Pearl Rhinestone Mini Dress

    Special Occasion

    A luxe strapless dress features countless faux pearls and rhinestone embellishments on a flattering bodycon mini-length silhouette. Perfect for homecoming or dressy parties.

    This dress proves that short and stylish is always a vibe. Want more? Discover our bold short prom dresses or find a celebration-ready fit in our party dresses.

    Fit & Features

    • Knit fabric lined with stretchy knit
    • Strapless neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Faux pearl and rhinestone embellishments
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2224

    Category Name: Night Out

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Small Rewards Mock Neck Corset Top

    It won't be long until you reap the rewards of this mock neck top! It features short sleeves and a center front slit accent atop a fitted corset-style bodice on a cropped hem. Complete the look in a denim mini skirt for a brunch.

    Fit & Features

    • Short sleeves, mock neck
    • Center front slit accent
    • Corset-style bodice
    • Cropped hem
    • Form-fitting design
    • Sleek stretch-knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4183

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Going-Out Chic Rhinestone Crop Top

    Elevate your going-out 'fits with this chic crop top! It features a sleeveless sweetheart neckline with a sparkly rhinestone embellished trim, a draped design at the bust, adjustable spaghetti straps, and a cropped, fitted hem. The crepe fabric offers a moderate stretch. Style with faux leather pants.

    Fit & Features

    • Sleeveless sweetheart neckline, rhinestone trim
    • Draped design at the bust
    • Adjustable spaghetti straps
    • Cropped, fitted hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4615

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Sparkly Glitter Off The Shoulder Dress

    What could be more fabulous than this glitter mini dress to show your sparkling style! With a sweetheart neckline, foldover short-sleeve cuffs, and a bodycon silhouette, this dress will flatter your every curve. The beautiful glitter knit fabric and front ruched seam add extra glam, sure to get you noticed. Complete the look with a clutch and heels for a birthday celebration!

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Foldover short-sleeve cuffs
    • Bodycon silhouette
    • Front ruched seam, mini-length hem
    • Glitter knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2675

    Category Name: Night Out

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step Out And Sparkle Rhinestone Strappy Block Heels

    Step out and sparkle in these fabulous rhinestone strappy block heels! They feature an open square-shaped toe, a knotted strappy design with sparkling rhinestone embellishments, thin adjustable ankle and heel straps with rhinestones, a block heel, and are composed of a faux leather material. Style with a metallic clutch for girl's night!

    Fit & Features

    • Open square toe
    • Knotted strappy design, rhinestone embellishments
    • Thin ankle and heel straps, buckle detail, rhinestone embellishments
    • Block heel
    • Faux leather material
    • Faux leather subtle cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4616

    Category Name: Night Out

    Price: $4.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Day Gal Strapless Ruffled Skater Dress

    Let your shoulders out in this strapless skater dress suited best for sunny days! This dress features a stretchy smocked bodice for a comfortable fit and a skater silhouette that will flatter your figure. The layered ruffled short-length hem adds a playful touch, and the cotton woven fabric ensures all-day comfort. Complete the look with a choker necklace.

    Fit & Features

    • Cotton woven fabric
    • Strapless straight neckline, no-slip strip
    • Stretchy smocked bodice
    • Layered ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5476

    Category Name: Night Out

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Cutest Denim V-Neck Mini Dress

    Show off your cute figure in this stylish denim mini-dress! It features a sleeveless sweetheart neck, wide shoulder straps, a front exposed zipper closure, and a bodycon silhouette. Complete the look in lace-up heels for a birthday party!

    Fit & Features

    • Sleeveless sweetheart neck
    • Wide shoulder straps
    • Front exposed zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-4591

    Category Name: Night Out

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Waist Satin Tapered Pants
    Tie your sleek look all together with these satin tapered pants! They feature a high rise waist, a tie front belt, a back zipper and hook and eye closure, and straight pant legs with a tapered hem. The satin-like fabric offers minimal stretch.

    Style Number/Barcode: 06402-0100

    Category Name: Night Out

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Way To My Heart Rhinestone Stiletto Heels

    You know the way to any girlz heart is a pair of heels, and these cuties have us giving heart eyes! 

    • Open pointed toe
    • Single band
    • Heart rhinestone buckle closure
    • Skinny stiletto heel
    • Faux leather

    Style Number/Barcode: 07401-1032

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale