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.

  • Starstruck Shine Glitter Mesh Mini Dress

    Leave everyone starstruck in this glitter mini dress! It features a one-shoulder neckline, fitted long sleeve, sheer mesh waist trim, bodycon silhouette, and a flirty front slit and mini-length hem on glitter crepe knit fabric that brings the shimmer. Complete the look in statement earrings.

    Fit & Features

    • One-shoulder neckline
    • Fitted long sleeves
    • Sheer mesh waist trim
    • Bodycon silhouette, front slit
    • Mini-length hem
    • Glitter crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-5115

    Category Name: Night Out

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back At It Short Sleeve Twist Crop Top

    Everyone will be looking back at you in this short sleeve crop top! Made with double-lined brushed knit fabric, this top is soft and comfortable. The twist open back adds a touch of unique style, while the cropped hem keeps you cool and stylish. Complete the look in trendy flare pants.

    Fit & Features

    • Double-lined brushed knit fabric
    • Twist open back
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5274

    Category Name: Night Out

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tapered And Chic Trouser Pants

    Tapered and chic, these trouser pants are a workwear staple! They feature a high-rise waist with belt loops, front pockets, faux back pockets, a fitted silhouette throughout the leg, and a subtle flared hem. The smooth woven fabric has minimal stretch. Style with a cropped blouse and mules.

    Fit & Features

    • High-rise waist
    • Belt loops, hidden front zipper, button, and hook and bar closures
    • Two front pockets, two faux back pockets
    • Fitted silhouette, subtle flared hem
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-0799

    Category Name: Night Out

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fly And Flossy Satin Rhinestone Party Dress

    Step out looking fly and flossy in this glam rhinestone satin dress for a bachelorette in Vegas or cocktail hour with friends! The short dress features a sleeveless square neck, adjustable spaghetti straps, a sultry cutout bodice, a flattering pleated side seam, a faux wrap skirt, and a mini-length hem. Complete the look with statement fringe earrings.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Cutout bodice, back zipper and hook-eye closure
    • Pleated side seam, faux wrap skirt
    • Mini-length hem
    • Rhinestone embellished
    • Lined satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05103-4986

    Category Name: Night Out

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Charmer Crop Top

    Charm them all with style with this sultry crop top! It features a sleeveless bodice, a single shoulder strap, and a majorly cropped hem. The snake printed top is composed of a lightweight knit fabric that offers plenty of stretch and a form hugging fit. Don't forget the matching mini skirt!

    Style Number/Barcode: 06001-1111

    Category Name: Night Out

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clear And Chic PVC Mules

    Keep it clear and chic with mules that match all your cute outfits. The mules feature an open back, a clear PVC strap, a square toe with a clear strap over the toe, and a lucite block heel. Complete look with a ribbed bodycon

    Fit & Features

    • Open back 
    • Clear PVC strap
    • Square toe
    • Clear strap over the toe
    • Lucite block heel

    Style Number/Barcode: 07401-2686

    Category Name: Night Out

    Price: $7.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feelin' Glam Metallic Stiletto Heels

    Feelin' glam? Elevate your outfits with these on-trend stiletto heels! They feature an open square toe, a thin strappy design, an adjustable heel strap, a pyramid stiletto heel, and a sleek chrome metallic finish. Style these shoes with a little black dress.

    Fit & Features

    • Open square toe
    • Thin strappy design
    • Adjustable heel strap, buckle detail
    • Pyramid stiletto heel
    • Chrome metallic iridescent finish
    • Runs true to size

    Style Number/Barcode: 07401-3522

    Category Name: Night Out

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Silhouette Long Sleeve Maxi Dress

    Create a chic silhouette in this curve-hugging maxi dress. It features a crew neckline, long fitted sleeves, a stylish cutout at the lower back, and a floor-length form-hugging fit with a side slit. Style this dress with clear heels.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Cutout at the lower back
    • Floor-length, form-hugging fit
    • Side slit
    • Cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4137

    Category Name: Night Out

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hey Stud Caged Stiletto Booties

    Look and feel like a total fashion stud in these stiletto booties! They feature an almond toe, side zipper, and a caged stud design on faux suede. Perfect for styling with a bodycon dress.

    Fit & Features

    • Almond toe
    • Side zipper
    • Stiletto heel
    • Caged stud design
    • Faux suede
    • Runs true to size

    Style Number/Barcode: 07403-1490

    Category Name: Night Out

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Solemate Criss-Cross Platform Heels

    Make this platform heels your new soulmate for night's out and formal occasions! Features a square toe, stiletto heel, criss-cross straps, buckle ankle strap on nubuck material. Complete the look in a little red dress.

    Fit & Features

    • Square toe, stiletto heel
    • Criss-cross straps
    • Platform sole
    • Buckle ankle strap
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07401-3641

    Category Name: Night Out

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Flow Halter Jumpsuit

    You love an effortless, carefree look, so this lightweight jumpsuit is perfect for your weekend plans. It features a sleeveless halter neckline, a center keyhole cutout, a backless design, a high waist seam, a form-hugging fit, and flared pant legs. Style with a layered charm necklace.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
    • Center keyhole cutout
    • Open back
    • High waist seam
    • Form-hugging fit, flared pant legs
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-1023

    Category Name: Night Out

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Ambition Faux Leather Thigh-High Boots

    If you've got high ambitions of being a chic trendsetter, these faux leather boots will help elevate your look! They feature a pointed toe, block heel, inner zipper closure, and a thigh-high shaft height. Complete your outfit with a sleek clutch.

    Fit & Features

    • Pointed toe
    • Block heel
    • Inner zipper closure
    • Thigh-high shaft height
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0916

    Category Name: Night Out

    Price: $4.97 $58.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Energy Glitter Velvet Long Sleeve Mini Dress

    This gorgeous glitter velvet mini dress will bring the luxe energy to your formal party looks! Crafted from a velvet fabric with sparkly glitter detailing in an intricate diamond-shaped pattern, this mini-length dress features a high crew neckline, long fitted sleeves, a V-back with a cross-over design and lower back cutout, and a bodycon silhouette. Complete your glitzy outfit with rhinestone fringe earrings.

    Fit & Features

    • Crew neckline, long fitted sleeves
    • V-back cross-over design
    • Lower back keyhole cutout, high waist seam
    • Mini-length hem, bodycon silhouette
    • Glitter detailing, diamond pattern
    • Velvet fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2949

    Category Name: Night Out

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Babe Strapless Lace-Up Cowboy Corset Top

    Unlock total western babe status in this cowboy corset top for country bars and bachelorettes! It features a strapless neckline and a western-inspired stitch design on faux leather fabric. The lace-up back adds a touch of unique style, while the cropped hem flaunts your figure. Complete the look in a denim skirt and cowboy boots.

    Fit & Features

    • Western-inspired stitch design
    • Faux leather fabric with sewn-in knit lining
    • Strapless neckline
    • Lace-up back
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2538

    Category Name: Night Out

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Studded Edge Pointed Kitten Pumps

    These pointed toe kitten pumps bring attitude with stud and grommet details. The low heel keeps them comfy while the hardware trim makes sure your look stays unapologetically bold.

    Fit & Features

    • 2.5" Kitten heel
    • Closed pointed toe, grommet and stud embellishments
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000422

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You Better Work Lace-Up Crop Top

    Work it out girl with a crop top that slays! The crop top features a sleeveless square neckline, tank shoulder straps, a lace-up back, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with high waist shorts and mules.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Lace-up back 
    • Cropped hem
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1684

    Category Name: Night Out

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesh With The Best Crop Top

    You only mess with the best style! This fab crop top features a round neck, long fitted sleeves, and a cropped hem. The bright neon yellow top is composed of a sheer and stretchy mesh fabric with a form hugging style. Bralette not included with garment.

    Style Number/Barcode: 06001-0911

    Category Name: Night Out

    Price: $5.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Slinky Knit One Shoulder Bodysuit
    Amp up your everyday style with this slinky knit bodysuit! It features a one shoulder neckline with a front strap detail, a single long fitted sleeve, and a thong bottom with dual snap button closures. The knit fabric offers moderate stretch and a form hugging fit.

    Style Number/Barcode: 06001-2137

    Category Name: Night Out

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Diva Over The Knee Boots

    Keep it divalicious with fierce leopard print! These faux suede boots feature an over the knee fit, a pointed toe, side zipper, and a block heel with a metal trim to accent. 

     

    Style Number/Barcode: 07402-0044

    Category Name: Night Out

    Price: $22.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cross Back Satin Mini Dress

    You slick chica, you. You'll be looking real smooth in this satin mini!

    Fits & Features

    • Square Neckline
    • Spaghetti Straps That Criss Cross At The Back 
    • Ruching Details At The Side
    • Mini Length Silhouette 
    • Satin-Like Composition I Fully Lined
    • Form Hugging Fit I Moderate Stretch

     

    Hunter & Charcoal: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0519

    Category Name: Night Out

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Look Lace-Up Block Heels

    Level up your 'fit and achieve that chic look with these faux leather heels! They feature an open square toe, a thin strappy lace-up design, and a block heel. Pair these shoes with a cute blouse and a high waist mini skirt.

    Fit & Features

    • Open square toe
    • Strappy lace-up design, tie closure
    • Block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-3852

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Chic Flocked Floral Sheer Mesh Top

    Prepare to get noticed when you're in this floral sheer mesh top with a form-hugging fit that flaunts your figure!

    Fit & Features

    • Sheer mesh fabric with velvet flocked floral pattern, moderate stretch
    • Cowl neckline
    • Hidden sheer mesh bralette with underwire, eyelash lace trim, back hook-eye closures
    • Adjustable spaghetti straps
    • Ruched side seams
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5522

    Category Name: Night Out

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Timeless Chic Plaid Belted Faux Wool Jacket

    Keep it timelessly chic in a plaid coat that is perf for the season! The plaid jacket features a collared neckline, long sleeves, a double breast button closure, faux front pockets, an adjustable belt with a square-shaped buckle, and a mid-thigh length. The jacket is is composed of a faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with ankle booties.

    Fit & Features

    • Plaid print
    • Collared neckline
    • Long sleeves
    • Double-breast button closure
    • Faux front pockets, adjustable belt 
    • Mid-thigh length 
    • Faux wool, minimal stretch
    • Runs true to size  

    Style Number/Barcode: 06201-0230

    Category Name: Night Out

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Silhouette Marble Mesh Midi Dress

    The silhouette of this trendy mesh midi dress will hug your curves! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the sides, and a mid-length hem. The sheer mesh fabric includes a full knit lining and an eye-catching marble print. Style this dress with clear mules.

    Fit & Features

    • Sleeveless square neckline, elastic band
    • Bungee spaghetti straps
    • Ruching down the sides
    • Mid-length, form-hugging silhouette
    • Sheer mesh fabric, knit lining, moderate stretch
    • Marble print
    • Runs true to size

    Style Number/Barcode: 05102-4330

    Category Name: Night Out

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale