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.

  • Lace Up In Mesh Crop Top

    Lace up in this sheer must have top! Pair with edgy pants and sleek stilettos for a look that's squad-approved! 

    Fit & Features

    • Mock Neck
    • Sheer Unlined Long Sleeves
    • Lace-Up Keyhole
    • Cropped Hem
    • Partially-Lined Mesh Fabric
    • Relaxed Fit
    • Moderate Stretch 

     

    Style Number/Barcode: 06001-2433

    Category Name: Night Out

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Classy Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch. Complete your chic look with mules and statement hoops

    Fit & Features

    • Collared neckline
    • Plunging v-wrap bust
    • Long sleeves with multi- buttoned cuff
    • Side ruched detailing
    • Mini length silhouette
    • Woven fabric
    • Form hugging fit, minimal stretch 

     

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

    Style Number/Barcode: 05102-1015

    Category Name: Night Out

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Clearly Stylish Lucite Block Heels

    Clearly you'll have a stylish 'fit in these trendy block heels! They feature an open almond toe with a clear toe strap and a sturdy clear lucite block heel. Pair these shoes with a little black dress for a fun girl's night out.

    Fit & Features

    • Open almond toe
    • Clear toe strap
    • Clear adjustable around the ankle strap with buckle detail
    • Open back
    • Clear lucite block heel
    • Patent PU material

    Style Number/Barcode: 07401-2412

    Category Name: Night Out

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Some Nights Asymmetrical Mini Dress

    Some nights call for a dressy vibe! Dress up in a mini dress that commands attention! The dress features a sleeveless V-neckline, padded cups, spaghetti straps, ruched side seams, and an asymmetrical mini-length silhouette. Complete look with clear mules and door knockers. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Padded cups
    • Ruched side seams
    • Asymmetrical mini-length silhouette 
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05103-3791

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dancer Spirit Lace-Up Block Heels

    Elegant and chic, switch your ballet shoes for these lace-up heels featuring a square toe, and block heel. Complete the look in a chiffon skater dress.

    Fit & Features

    • Square toe
    • Block heel
    • Lace-up tie closure
    • Runs true to size

    Style Number/Barcode: 07401-3773

    Category Name: Night Out

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold And Belted Sleeveless Jumpsuit

    Keep it bold in a belted jumpsuit for an iconic diva, like yourself! The jumpsuit features a strapless square neckline, a wide adjustable belt with an O-ring buckle, and a straight leg fit with a flared hem. The jumpsuit is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules and door knocker earrings.

    Fit & Features

    • Strapless square neckline
    • Wide adjustable belt
    • O-ring buckle
    • Straight leg fit, flared hem
    • Lined crepe fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0649

    Category Name: Night Out

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Total Vibe Halter Bodysuit

    You in this sultry-chic bodysuit would be a total vibe! Featuring a sleeveless twist-front halter neckline with a center keyhole cutout at the bust, this bodysuit will elevate your basic look. Style with a faux leather skirt and mules.

    Fit & Features

    • Sleeveless twist-front halter neckline
    • Center keyhole cutout
    • Open back
    • Thong bottom, dual snap-button closure
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4808

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • Sultry And Stunning Halter Mesh Mini Dress

    Sultry and stunning, this mesh mini dress is a must-have for your next GNO! It features a sleeveless square neckline, thin halter straps that tie at the back of the neck, ruching down the sides, and a short, curve-hugging fit. The sheer mesh fabric has a nude knit lining. Style this dress with sleek hoops.

    Fit & Features

    • Sleeveless square neckline
    • Thin halter straps, tie at the back of the neck
    • Ruched sides
    • Mini-length, form-fitting silhouette
    • Sheer mesh fabric, nude knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3907

    Category Name: Night Out

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Contemporary Moves Stiletto Heels

    Shift towards a chic contemporary style in these nubuck heels featuring an almond toe, stiletto heel, wide toe strap, and criss-cross ankle straps with buckle closure. Complete the look in a statement crossbody purse.

    Fit & Features

    • Almond toe
    • Stiletto heel
    • Wide toe strap
    • Criss-cross ankle straps, buckle closure
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07401-3975

    Category Name: Night Out

    Price: $4.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Out To Sparkle Satin Rhinestone Heels

    Step out to sparkle in these shimmering satin heels for your next formal occasion! They feature a square toe, rhinestone-embellished asymmetrical straps that wrap around your foot and ankle, a low block heel, and a slip-on and off styling. Complete the look with a glitzy clutch.

    Fit & Features

    • Square toe
    • Rhinestone-embellished asymmetrical straps
    • Wrap design
    • Low block heel
    • Slip-on and off styling
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-4369

    Category Name: Night Out

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day To Night Strappy Faux Leather Block Heels

    These faux leather heels are essential for taking your look from day to night! They feature a sleek square toe, dual straps, a block heel to elevate the style, and a cushioned footbed for ultimate comfort. Complete the look with a chic hair accessory.

    Fit & Features

    • 3.5" Block Heel
    • Square toe
    • Dual straps
    • Cushioned footbed
    • Faux leather material
    • Silver and gold are metallic
    • Runs true to size

    Style Number/Barcode: 07401-5014

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Giving Bold Chain Necklace And Bracelet Set

    Giving bold, giving polished, giving it girl. This chunky necklace and bracelet set is your go-to for instantly elevating any 'fit—stack it or stunt it solo.

    Fit & Features

    • Necklace and bracelet set
    • Chunky chain-link design
    • Lobster clasp closures with extenders

    Style Number/Barcode: 07002-000058

    Category Name: Night Out

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Velvet Lace-Up Crop Top

    Get a sultry vibe for your next holiday party in this luxe velvet crop top! It features a mock neckline, long fitted sleeves, an open back with a lace-up detail, and a cropped, form-fitting style. Pair this top with high rise faux leather joggers for an edgy-chic look.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Open back with lace-up detail
    • Cropped
    • Form-hugging fit
    • Ribbed velvet knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06001-2987

    Category Name: Night Out

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Polished N' Edgy Faux Leather Paper Bag Pants

    Keep it polished and edgy with chic faux leather pants! The paper bag pants feature a high-rise waist, a single button and zipper closure, slanted pockets, and a skinny leg with a tapered hem. The pants are composed of a faux leather fabric that offers a form-hugging fit. Complete the look with a bustier and mules.

    Fit & Features

    • High rise paper bag waist
    • Single-button and zipper closure
    • Slanted pockets
    • Skinny leg with a tapered hem 
    • Back pockets
    • Faux leather fabric with minimal stretch
    • Form-hugging fit

    Style Number/Barcode: 06402-0305

    Category Name: Night Out

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cinched And Chic Faux Leather Trench Coat

    Create a chic cinched silhouette with this sleek faux leather trench coat. Featuring a lapel collar, long sleeves, an off-center zip-front, a belted waist, and a fitted silhouette, this jacket will amp up your winter 'fits. Layer over a sweater dress with knee-high boots.

    Fit & Features

    • Lapel collar, long sleeves
    • Off-center zip-front
    • Single chest pocket flap
    • Belted waist, rectangular buckle
    • Fitted silhouette
    • Faux leather material, sewn-in woven lining
    • Runs true to size

    Style Number/Barcode: 06204-1520

    Category Name: Night Out

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Season To Shine Metallic Rhinestone Mules

    It's the season to shine! Arrive in sparkly style in these metallic mules featuring a square toe, dazzling rhinestone embellished asymmetrical straps, and a comfortable short block heel. Complete the look with a chic clutch for a dance or banquet!

    Fit & Features

    • Square toe
    • Rhinestone embellished asymmetrical straps
    • Short block heel
    • Luxe fit cushioned insole
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-4628

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bead It Embellished Lace Bustier

    Easy on the embellishment? Nah, so not you! Glam it up in this gorgeous beaded bustier. The bustier features a sleeveless sweetheart neckline, padded cups, and removable adjustable spaghetti straps. The bodice features rhinestone with gemstone embellishments and an embroidered floral design. Complete look with a faux leather wrap skirt.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded cups
    • Removable adjustable spaghetti straps
    • Rhinestone and gemstone embellishments
    • Cropped hem
    • Lined lace fabric
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 06003-1485

    Category Name: Night Out

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek 'Fit Wrap-Front Satin Mini Skirt

    Show off a sleek 'fit with this silky satin woven mini skirt! It features a high-rise waist, a faux wrap-front design with a tie waist accent, and a short, fitted silhouette. Style with a corset and heels for a night out.

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Faux wrap-front design, tie waist detail
    • Mini-length hem, form-hugging fit
    • Smooth satin woven fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0501

    Category Name: Night Out

    Price: $3.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Square Rhinestone Earrings

    Ooze glamour and class with these dazzling studs! These earrings feature a large rose gold square embellished with gleaming rhinestones for an uber chic look! Includes post back closure with sturdy hard plastic disc for a secure fit.

    Style Number/Barcode: 07001-3828

    Category Name: Night Out

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Glam Mini Dress

    Add a touch of classic glam to your look with this chic mini dress. It features an off the shoulder square neckline, short sleeves, a front waist cut out with a scalloped hem, and a short, form hugging fit. The dress is composed of a sheer glitter lace fabric with a knit lining. Glitter may transfer.

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

    Style Number/Barcode: 05103-0213

    Category Name: Night Out

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cheer Squad Ponte Pleated Mini Skirt

    The crowd will cheer for you in this cute pleated mini skirt featuring a high-rise waist and an A-line silhouette. Composed of a Ponte knit fabric with an inner shorts lining. Finish the look in a crop top and sneakers.

    Fit & Features

    • High-rise waist
    • Pleat detailing
    • A-line silhouette
    • Mini-length hem
    • Ponte knit fabric, inner shorts lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0658

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Absolute Diva Baguette Rhinestone Block Heels

    Step out like an absolute diva in these exclusive nubuck block heels! Designed with a sleek square toe and thin block heel for a modern look. The baguette rhinestone embellished straps add a touch of glamour, while the lightly cushioned faux leather footbed provides comfort. Complete the look in a satin cocktail dress for a semi-formal event!

    Fit & Features

    • 3.5" Thin Block Heel
    • Square toe
    • Baguette rhinestone embellished straps
    • Buckle closure
    • Lightly cushion faux leather footbed
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07401-4672

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natalia Metallic Ruched Midi Dress

    Special Occasion 

    Natalia brings the shine from all your best angles! She features a plunging V neckline, long fitted sleeves and a curve enhancing midi length silhouette with ruched detailing along the sides. Dress is composed of a lined metallic knit fabric that offers a moderate stretch. Dress includes a back zipper closure with hook and eye closure for secure fit.

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0229

    Category Name: Night Out

    Price: $24.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance