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.

  • Easy Attention Strapless Slit Crop Top

    Capture attention easily in this strapless crop top this spring or summer! The strapless neckline bares your shoulders and the adjustable drawstring helps you achieve the perfect fit, while the slit accent and asymmetrical crop hem flaunt your figure. Complete the look in skinny jeans and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Front adjustable drawstring
    • Slit accent
    • Cropped asymmetrical hem
    • Runs true to size

    Style Number/Barcode: 06002-1807

    Category Name: Night Out

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Special Surprise Rhinestone Spiral Stiletto Heels

    Step out to stand out in these rhinestone stiletto heels made to surprise everyone with your glamour! These stunning stiletto shoes feature an almond toe and rhinestone embellished straps for a touch of glamour. The unique spiral ankle design adds a modern twist. Complete the look with statement earrings.

    Fit & Features

    • 4" Stiletto heel
    • Almond toe
    • Rhinestone embellished straps, spiral ankle
    • Blue Heel: chrome material trim
    • Pink Heel: nubuck material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4701

    Category Name: Night Out

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Look Pointed Toe Buckle Slingback Flats

    On the go? Slip on these faux leather flats for a trendy look that's always effortless! They feature a closed pointed toe, dual grommet buckle accent straps for an edgy flair, and an open ankle with a strap. Complete the look with sunglasses for any plans!

    Fit & Features

    • Closed pointed-toe
    • Dual grommet buckle accent straps
    • Open ankle with strap
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-0102

    Category Name: Night Out

    Price: $15.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vintage Glam Platform Mary Jane Heels

    Fit & Features

    • Block heel
    • Faux nubuck material
    • Closed pointed-toe
    • Adjustable ankle strap with rhinestone buckle
    • Platform sole
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-5070

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruby Formal Sequin Lace-Up Midi Dress

    Special Occasion

     Light-catching sequins shape the Ruby formal dress to bring sparkle to dinner banquets and engagement parties! She features a sleeveless plunge sweetheart neck with a v-wire insert, spaghetti straps, a lace-up back design, a bodycon fit, and a flirty slit along her midi-length hem. The formal dress is composed of a sequin scroll mesh fabric with a knit lining and minimal stretch. Style with teardrop earrings and heels to complete the look!

    Fit & Features

    • Sleeveless plunge sweetheart neck, v-wire insert
    • Spaghetti straps, back zipper and hook-eye closure
    • Lace-up back design
    • Bodycon fit, front slit, midi-length hem
    • Sequin scroll mesh fabric, knit lining, minimal stretch
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05001-1284

    Category Name: Night Out

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Futuristic Babe Metallic Strappy Block Heels

    The future is looking so sleek in these metallic block heels! They feature an almond toe, a trio of thin straps, and a closed ankle with a back zipper closure. Style with an embellished box clutch to complete the look!

    Fit & Features

    • Almond toe
    • A trio of thin straps
    • Closed ankle, back zipper closure
    • Block heel
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-4139

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Sophisticated Trench

    Turn heads with this chic and sophisticated trench! It features a drape front with a flat lapel collar, long sleeves, an elastic banded back with a tie front, and a relaxed, flowy fit. The trench is composed of a sheer woven fabric with no stretch.

    Style Number/Barcode: 06204-4771

    Category Name: Night Out

    Price: $10.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bohemian Fringe Rhinestone Earrings

    Make a statement with these earrings that will make your add a unique touch to your look! Earrings feature an oval on post and a bohemian fringe design adorned with mini rhinestones. Includes a post back closure.

     

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

    Style Number/Barcode: 07001-0089

    Category Name: Night Out

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Drama Queen Energy Chiffon Corset Top

    Cue the compliments—this off-the-shoulder corset top is giving full fairytale fantasy with a side of spice, with cute lace-up sides and flexible boning that snatches your look. 

    Fit & Features

    • Chiffon fabric, bust knit lining
    • Off-the-shoulder neckline, bust tie
    • Ruffled short-sleeve cuffs
    • Stretchy smocked back
    • Side lace-up detail
    • Flexible boning inserts, cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000092

    Category Name: Night Out

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Natural Attraction Mini Knot Dress

    Create a natural attraction with a simply flattering look! This mini dress features a v neckline, long sleeves that puff at the wrist with a thick band, and a front knot detailing at the center of the bodice. Skirt meets bodice with a wrap design and an asymmetrical hemline that meets mid thigh. Dress is composed of a smooth knit material with a sheen reflection and moderate stretch.

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

    Style Number/Barcode: 05101-0200

    Category Name: Night Out

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Come Thru Clear Heeled Booties

    Come thru with that style baby boo! We are loving a clear heel, so this is one for the girls that live for a trendy pair of booties!

    • Ankle fit
    • Almond toe
    • Rectangular clear lucite heel
    • Inner zipper closure
    • Faux leather

    Style Number/Barcode: 07403-0206

    Category Name: Night Out

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Thinking About You One Shoulder Mini Dress

    Leave them thinking about you with a mini dress that stuns with stylish accents! The dress features a one-shoulder neckline, a twist-knot accent at the bodice, an asymmetrical shoulder strap, and a mini-length silhouette. The dress is composed of a soft-to-the-touch brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a dainty necklace.

    Fit & Features

    • One-shoulder neckline
    • Asymmetrical shoulder strap
    • Twist knot accent
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05103-4129

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually-Chic Bodycon Mini Dress

    Showcase a casually-chic look in this slinky knit bodycon mini dress. It features a one-shoulder neckline, a single long balloon sleeve, a high waist with a trendy side cutout, and a short, curve-hugging fit. Style this dress with clear heels.

    Fit & Features

    • One-shoulder neckline
    • Single long balloon sleeve, elastic cinched hem
    • High waist, side cutout
    • Ruching down one side
    • Mini-length, form-fitting silhouette
    • Slinky knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1355

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lots To Love Block Heel Booties

    There is a lot to love about these nubuck booties and all the ways you can style them! They feature an almond toe, block heel, and side zipper closure, and fit above the ankle. Complete the look in a chic duster trench coat for a day in the city!

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Above the ankle length
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1570

    Category Name: Night Out

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edge Up Your Look Faux Leather Mini Skirt

    Edge up your going-out look with this sleek faux leather mini skirt. It features a high-rise waist, a back zipper closure, a mini-length hem with a chic short side slit, and a form-hugging fit. The smooth faux leather fabric has no stretch. Pair with a corset top and clear heels.

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Mini-length hem
    • Short side slit
    • Form-hugging fit
    • Smooth faux leather fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06401-0584

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Jillian Sequin Cutout Party Dress

    Special Occasion

     Fun, flirty, and fab! Show up to the party in the Jillian sequin dress designed in a sleeveless sweetheart neckline with adjustable spaghetti straps to customize the fit, a padded bust, and a front and back cutout leading to the bodycon short-length hem. The formal dress is composed of a sequin woven fabric with a knit lining and no stretch. Complete your dressy look in a ring set and heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Padded bust, bra optional
    • Front and back cutouts
    • Bodycon, short-length hem
    • Sequin woven, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05001-1349

    Category Name: Night Out

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkling Beauty Rhinestone Block Heels

    A block heel that unlocks your inner sparkling beauty! They feature a square toe, a rhinestone embellished toe strap, a closed ankle, and an adjustable ankle strap with buckle closure. Complete the look with a glitzy clutch purse for a special occasion!

    Fit & Features

    • Square toe
    • Rhinestone embellished toe strap
    • Closed ankle
    • Adjustable ankle strap with buckle closure
    • Block heel
    • Runs true to size

    Style Number/Barcode: 07401-4002

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Velvet Vibe Floral Mini Dress

    You in this chic floral velvet mini dress will be such a stylish vibe! The dress features a sleeveless scoop neckline, spaghetti straps, and a short, form-hugging silhouette. The sheer knit fabric includes a full knit lining and an all-over velvet burnout floral pattern. Complete the look with heels and rhinestone earrings.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Sheer knit fabric, full knit lining, moderate stretch
    • Velvet burnout floral pattern
    • Runs true to size

    Style Number/Barcode: 05101-1170

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel Me Velvet Bustier Mini Dress

    You'll be feeling yourself for a fab night out in this velvet mini dress designed to define your curves for a jaw-dropping effect! The bodycon dress features a sleeveless sweetheart neck, adjustable spaghetti straps, built-in padded bust, and flexible boning inserts. Complete the look in PVC heels.

    Fit & Features

    • Sleeveless sweetheart neck, adjustable spaghetti straps
    • Built-in padded bust, back zipper closure
    • Flexible boning inserts
    • Bodycon silhouette
    • Mini-length hem
    • Lined velvet fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05103-4495

    Category Name: Night Out

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Sparkle Asymmetrical Midi Dress

    Showcase a chic sparkle in this fitted crepe midi dress. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a rhinestone embellished asymmetrical trim across the front, ruching, and a midi-length, form-hugging fit with an asymmetrical cut hem. Style with stilettos.

    Fit & Features

    • Sleeveless square neckline, dart seam detailing
    • Adjustable spaghetti straps
    • Back zipper closure
    • Rhinestone embellished asymmetrical trim
    • Ruching
    • Midi-length, form-fitting silhouette, asymmetrical cut hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1798

    Category Name: Night Out

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jovie Sequin Glitter Sheer Mesh Mini Dress

    Special Occasion

    The Jovie sequin glitter corset mini dress elevates every night on the town! The party dress showcases a sheer floral embroidered corset bodice with plenty of skin while the bodycon silhouette flaunts your figure. Pair with earrings.

    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

    • Sheer mesh fabric, minimal stretch
    • Glitter floral embroidered design, sequins
    • Sheer corset-style bodice, sheer nude-tone lining, contrast piping, flexible boning
    • Sleeveless V-neckline, padded bust, adjustable spaghetti straps
    • Low back design, zipper with hook-eye closure
    • Lined mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05001-000104

    Category Name: Night Out

    Price: $59.90

    Availability: In Stock

    Available Color: WINE

    Available Size: L

  • Be Your Sweetheart Satin Lace-Up Skater Dress

    Show up ready to swoon every heart in this satin skater dress at parties! It features a strapless sweetheart neckline with non-slip grip lining, a pleated bust overlay, an eye-catching strappy lace-up back, and a short-length hem. Complete the look with a rhinestone choker and earrings!

    Fit & Features

    • Strapless sweetheart neckline
    • Non-slip grip lining
    • Pleated bust overlay
    • Strappy lace-up back 
    • Skater silhouette, short-length hem
    • Silky satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2566

    Category Name: Night Out

    Price: $5.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Of All Ribbon Bow Bodycon Mini Dress

    You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Square neckline
    • Satin ribbon bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5655

    Category Name: Night Out

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clearly Fab Platform Block Heels

    These platform block heels are clearly fab and on-trend! They feature an open square toe with a strap, an adjustable ankle strap, a stylish platform, and a clear lucite block heel. Pair these shoes with your fave casual dress to elevate the look!

    Fit & Features

    • Open square toe, toe strap
    • Adjustable ankle strap, buckle detail
    • Platform
    • Lucite block heel
    • Faux nubuck material
    • Runs true to size

    Style Number/Barcode: 07401-3281

    Category Name: Night Out

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale