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.

  • Clear That Up PVC Lucite Mules

    It's time to clear things up, and make sure you're the most stylish babe in the room! This pair of super chic mules feature PVC straps, a clear lucite block heel, and an open toe. Wear them with a classic tank and bike shorts for a street-style ready vibe. 

    Fit & Features

    • Open toe
    • PVC straps
    • Lucite block heel
    • Runs true to size

    Style Number/Barcode: 07401-2999

    Category Name: Night Out

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slit Happens Faux Suede Midi Skirt

    This faux suede midi skirt happens to be very stylish for coffee runs and beyond! It features a high-rise waist, front slit accent, zipper closure, and a fitted midi hem. Complete the look with chic booties and a handbag.

    Fit & Features

    • High-rise waist, slit accent
    • Fitted, midi hem
    • Zipper closure
    • Faux suede fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06401-0425

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lace Setter Corset Crepe Dress

    Set the trend for your squad in this romantic lace mini dress featuring a sleeveless, sweetheart neck, ruffled adjustable spaghetti straps, lightly padded bust, and a corset-style lace bodice atop the form-fitting crepe lined hem. Complete the look in PVC strap heels.

    Fit & Features

    • Sleeveless, sweetheart neck
    • Ruffled adjustable spaghetti straps
    • Lightly padded bust
    • Back zipper closure
    • Corset-style lace bodice
    • Form-fitting, mini-length hem
    • Crepe lined fabric, minimal stretch, fits true to size

    Style Number/Barcode: 05101-1680

    Category Name: Night Out

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raquel Formal Rhinestone Velvet Mini Dress

    Special Occasion

    The Raquel formal rhinestone velvet mini dress will showcase elite glamour at your next fancy affair! She features a sweetheart neckline, long fitted sleeves, dual high waist seams, a chic faux wrap-front design with a mini-length hem, a bodycon silhouette, and all-over iridescent round rhinestones in vertical and horizontal embellished patterns for a gorgeous multi-hue sparkle. The luxe velvet fabric has a moderate stretch. Complete your look in this mini dress with metallic heels.

    Fit & Features

    • Sweetheart neckline, long fitted sleeves
    • Square back design, zipper, hook and eye closure
    • Dual high waist seams, faux wrap-front design, mini-length hem, bodycon fit
    • Iridescent round rhinestones, vertical and horizontal embellished patterns
    • Velvet fabric, knit lining at the bust, moderate stretch
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1877

    Category Name: Night Out

    Price: $9.97 $74.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Glam Rhinestone Strappy Clear Toe Pumps

    Step out and shine with all the glamour in these rhinestone strappy clear toe pumps! They feature a closed pointed toe with a clear PVC material, a rhinestone-embellished strappy design with a center knot detail, rhinestone-adorned adjustable ankle and heel straps, and a stiletto heel. Style these pumps with a metallic clutch!

    Fit & Features

    • Closed clear PVC pointed toe
    • Rhinestone strappy design, center knot detail
    • Rhinestone adjustable ankle and heel straps, buckle detail
    • Open back
    • Stiletto heel
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4570

    Category Name: Night Out

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glamorous Goddess One-Shoulder Mini Dress

    Step out like a glam goddess in this one-shoulder mini dress! Featuring a sheer ruched fitted long sleeve, and side waist cutout, this dress will flatter your figure and make a statement. The mesh fabric and marble print with glitter trim add a touch of glamour to the bodycon silhouette and mini-length hem. Complete the look in strappy block heels for a night out!

    Fit & Features

    • One shoulder neckline
    • Sheer ruched fitted long sleeve
    • Side waist cutout, side ruched seams
    • Bodycon silhouette, mini-length hem
    • Marble print, glitter trim
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-5477

    Category Name: Night Out

    Price: $6.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Time Long Sleeve Rhinestone Mesh Bolero

    It's time to add that pop of glitz and glam with this long sleeve rhinestone mesh bolero! Designed with an airy sheer mesh fabric offering plenty of stretch, the lightweight layer is embellished with all-over mini rhinestones with a dreamy iridescent hue. The bolero features an open front, long fitted sleeves with lettuce edge hems with slit accents, and an ultra-cropped hem. Style over your fave party dresses!

    Fit & Features

    • Stretchy sheer mesh fabric
    • Iridescent rhinestones
    • Open front
    • Long fitted sleeves, lettuce edge hems with slits
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0446

    Category Name: Night Out

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shining Star Cowl Neck A-Line Glitter Mini Dress

    Everyone will remember the way you sparkled in this glitter mini dress! With delicate spaghetti straps and a stunning cowl neckline, this dress will accentuate your curves in all the right places. The padded bra cups provide support and comfort, while the A-line silhouette and front slit add a flattering touch. Complete the look in high heels and earrings!

    Fit & Features

    • Glitter knit fabric, stretchy knit lining
    • Spaghetti straps
    • Cowl neckline
    • Padded bra cups
    • A-Line silhouette
    • Front slit 
    • Runs true to size

    Style Number/Barcode: 05103-5658

    Category Name: Night Out

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Velvet Vixen Mini Dress

    Vamp up your look with sultry velvet

    Fits & Features

    • Scoop Neckline I Unlined Floral Lace Trim
    • Spaghetti Straps
    • Mini Length Silhouette With Matching Lace Hem
    • Lined Velvet Fabric 
    • Curve Hugging Fit I Moderate Stretch
    • Zipper Not Included

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

    Style Number/Barcode: 05103-0147

    Category Name: Night Out

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty Pleated Tie Waist Blouse

    Pretty and pleated, this blouse will tie your look together. It features a slight sweetheart neckline, long sheer billowy sleeves with elastic banded cuffs, pleated details across the chest, a sheer back followed by a tie waist accent, and a cropped fit. The top is composed of a lightweight chiffon fabric with no stretch and includes a front knit lining.

    Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0365

    Category Name: Night Out

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mock Neck Chiffon Mini Dress

    Girl, you'll be rocking this dress! 

    Fits & Features

    • Elastic Mock Neckline 
    • Sheer Chiffon Bodice With Long Bell Sleeves
    • Embroidery Detailing Throughout 
    • Smocked Midsection
    • Fully Lined, Tiered, Ruffle Mini Length Hemline 
    • Relaxed Fit | Moderate Stretch

      Style Number/Barcode: 05101-0607

      Category Name: Night Out

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Hit Your Mark Faux Leather Moto Vest

      An edgy faux leather vest featuring a collared neckline, snap buttons, and front zipper closures give it a functional style while the cropped length hem keeps it modern. 

      Fit & Features

      • Faux leather material, sewn-in woven lining
      • Collared neckline
      • Snap buttons and front zipper closures
      • Cropped length hem
      • Runs true to size

      Style Number/Barcode: 06204-1843

      Category Name: Night Out

      Price: $9.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Add Some Edge PU Mini Skirt

      Add some effortless edge to your look with this chic little mini skirt!

      Fit & Features

      • High rise waist
      • Front foldover details with faux buttons
      • Front zipper closure
      • Two front zippered faux pockets
      • Short, form hugging fit
      • PU fabric | Moderate stretch

      Style Number/Barcode: 06401-0163

      Category Name: Night Out

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • She's Got It Ruched Mini Skirt

      Serve up that wow factor in a skirt that stuns! Perfect for a night out with the squad, this skirt features a high rise waist, ruched detailing throughout, and a mini length silhouette. Complete your look with the matching crop top and a pair of clear heels

      Shop Matching Crop Top: She's Got It Ruched Crop Top

      Fit & Features

      • High rise waist
      • Ruching
      • Lined mesh fabric
      • Form hugging fit
      • Matching crop top sold separately 

       

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

      Style Number/Barcode: 06501-0249

      Category Name: Night Out

      Price: $6.97 $18.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Dangerous Woman Faux Patent Leather Crop Top

      Something about this crop top will make you want to channel your edgy side. The crop top features a sleeveless square neckline, adjustable spaghetti straps, and a cropped hem. The top is composed of a faux patent leather fabric that offers a form-hugging fit. Complete your look with the matching skirt.

      Shop Matching Skirt: Dangerous Woman High Waist Mini Skirt

      Fit & Features

      • Sleeveless square neckline
      • Adjustable spaghetti straps
      • Cropped hem
      • Back zipper closure
      • Faux patent leather 
      • Form-hugging fit
      • Matching skirt sold separately 

      Style Number/Barcode: 06003-1167

      Category Name: Night Out

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Charming And Chic Snake Print Flared Pants

      Shake up your warm-weather wardrobe with these charming and chic snake print flared pants! They feature a high rise banded waist with a form-hugging fit and a flared out hem. The lightweight brushed knit fabric offers plenty of stretch. Pair these pants with the matching top and some chic new accessories.

      Shop Matching Top: Charming And Chic Snake Print Crop Top

      Fit & Features

      • High rise banded waist
      • Form-hugging fit
      • Flared hem
      • Brushed knit fabric
      • Snake print
      • Runs true to size

      Style Number/Barcode: 06502-0502

      Category Name: Night Out

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Polished And Chic Faux Wool Trench Coat

      Keep it polished and chic with a trench that brings the sophistication to your look! The coat features a lapel collar, a drape open front, a removable belt with loops, side pockets, long sleeves, and a mid-thigh length. The jacket is composed of a faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with thigh-high boots and a bodysuit

      Fit & Features

      • Lapel collar, draped open front 
      • Removable belt with loops
      • Side pockets
      • Long sleeves
      • Mid-thigh length 
      • Faux wool fabric 
      • Relaxed fit, minimal stretch, runs true to size 

      Style Number/Barcode: 06201-0241

      Category Name: Night Out

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Holiday Sparkle Sequin Faux Wrap Skirt

      Shine bright this holiday season in this chic sequin skirt! It features a high-rise waist and a faux wrap on a mini-length hem. Complete the look with the matching top.

      Shop Matching Top: Holiday Sparkle Sequin Crop Top

      Fit & Features

      • High-rise waist
      • Faux wrap
      • Mini-length hem
      • Sequin lined-knit fabric
      • Moderate stretch
      • Fits true to size

      Style Number/Barcode: 06401-0345

      Category Name: Night Out

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • High Fashion Tie Waist Wide-Leg Jumpsuit

      Take care of business in this high fashion jumpsuit featuring long sleeves, an off-the-shoulder neckline, tie waist, and wide-leg silhouette. Composed of rib knit fabric with a moderate stretch. Perfect for styling with a blazer.

      Fit & Features

      • Long sleeves
      • Off-the-shoulder neckline
      • Tie-waist
      • Wide-leg silhouette
      • Rib-knit fabric, moderate stretch
      • Fits true to size

      Style Number/Barcode: 06502-0744

      Category Name: Night Out

      Price: $6.97 $54.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Night To Remember Cross Halter Bodycon Dress

      You're sure to remember the night looking so chic in this bodycon dress! It features a cross halter neckline with a keyhole accent, all-over ruching to accentuate your curves, and a mini-length hem. The dress is composed of a mesh-knit lined fabric with a moderate stretch. Complete the look in rhinestone hoops and stiletto heels.

      Fit & Features

      • Cross halter neckline
      • Keyhole accent
      • All-over ruching
      • Mini-length hem
      • Mesh-knit lined fabric
      • Moderate stretch
      • Fits true to size

      Style Number/Barcode: 05103-4273

      Category Name: Night Out

      Price: $9.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Babe Next Door Denim Mini Dress

      You'll look like a total babe next door in this adorable denim mini dress. It features a sleeveless sweetheart neckline with a padded bust, thin adjustable straps, an exposed back zipper closure, and a short, form-hugging fit. Style with hoop earrings and trendy cowgirl boots.

      Fit & Features

      • Sleeveless, sweetheart neckline, adjustable spaghetti straps
      • Built-in padded bust
      • Back zipper, hook-eye closure
      • Mini-length hem
      • Form-fitting silhouette
      • Denim fabric, minimal stretch
      • Runs true to size

      Style Number/Barcode: 05102-4448

      Category Name: Night Out

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sixties Queen Swirl Mesh Crop Top

      Take reign of your title in this retro mesh crop top featuring a sleeveless, v-neck, adjustable spaghetti straps, and a flirty front keyhole with tie, ruched bodice, and a swirl print. Complete the look in a denim skirt and booties.

      Fit & Features

      • Sleeveless, v-neck, adjustable spaghetti straps
      • Front keyhole with tie
      • Ruched bodice
      • Cropped hem
      • Swirl print, lined mesh fabric, moderate stretch
      • Fits true to size

      Style Number/Barcode: 06001-4199

      Category Name: Night Out

      Price: $6.97 $19.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Simply Lovely Crepe Rosette Mini Dress

      Feel simply lovely in the crepe mini dress to add a touch of romance to your wardrobe! It features sheer mesh peasant long sleeves with a rose velvet pattern and elastic cuffs, a sweetheart neckline, a built-in padded bust with underwire and rosette appliques, plus a flattering bodycon silhouette and mini-length hem. Complete the look in platform heels and a clutch for a dinner party or dressy date night!

      Fit & Features

      • Sheer mesh peasant long sleeves
      • Rose velvet pattern, elastic cuffs
      • Sweetheart neckline, back zipper and hook-eye closure
      • Built-in padded and underwire bust, rosette appliques
      • Bodycon silhouette, mini-length hem
      • Crepe fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05101-2691

      Category Name: Night Out

      Price: $6.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Vampy Vibes Faux Leather Midi Dress

      This sleek faux leather midi dress will bring the vampy vibes to your going-out look. It features a strapless straight-across neckline, ruching at the waist, a midi-length hem with a chic back slit accent, and a bodycon silhouette to flaunt your figure. The faux leather fabric offers a moderate stretch. Style this midi dress with lace-up stilettos for an edgy night-out 'fit.

      Fit & Features

      • Strapless straight-across neckline
      • Back zipper, hook and eye closure
      • Dart seams, high waist seam, ruching at the waist
      • Midi-length hem, back slit
      • Bodycon silhouette
      • Faux leather fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05103-5282

      Category Name: Night Out

      Price: $5.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale