Night Out

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.

  • Spring Mentality Ditsy Floral Ruffle Mini Skirt

    You'll be beyond ready for all the things spring will bring in this ditsy floral ruffle mini skirt! Crafted from a soft brushed knit fabric showcasing an adorable floral print, this skirt is truly one-of-a-kind. Featuring a high-rise waist, a front adjustable drawstring so you can customize the style, and a flirty ruffled hem on the bodycon silhouette. Complete the look in a basic top and wedges!

    Fit & Features

    • Brushed knit fabric, ditsy floral print
    • High-rise waist
    • Adjustable drawstring
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06501-1023

    Category Name: Night Out

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • High Class Faux Leather Wrap Mini Skirt

    Perfect for a high-class night on the town, this faux leather mini skirt is the one you need! Featuring a high-rise waist and a chic wrap front design, this bodycon skirt is designed to accentuate your curves. Made with faux leather fabric, it adds a touch of sophistication to any outfit. Complete the look in a long sleeve bodysuit and heels!

    Fit & Features

    • Faux leather fabric, minimal stretch
    • High-rise waist
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06501-1024

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Exceptional Vibes Mid-Rise Ruffle Chiffon Skort

    The exceptional vibes of this chiffon skort will make you feel confident and chic all day long! The mid-rise waist and front tie with a cinched detail create a form-hugging fit that flatters your figure. And the ruffled mini-length hem adds a fun and flirty touch to your look. Style this skort with a cute short sleeve top and sneakers.

    Fit & Features

    • Chiffon fabric, shorts lining, no stretch
    • Mid-rise waist
    • Side zipper and hook-eye closure
    • Front tie with cinched detail
    • Form-hugging fit
    • Ruffled
    • Runs true to size

    Style Number/Barcode: 06403-0439

    Category Name: Night Out

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk On The Wild Side Leopard Mesh Mini Dress

    Walk on the wild side in this leopard mesh mini dress perfect for brunch or dates! This daring dress features a flattering square neckline, delicate spaghetti straps, and a surplice bodice for a flattering look. The side ruched seams accentuate your curves, giving you a bodycon fit that will make you stand out in any crowd. And with its mini-length hem and fierce leopard print, this dress is perfect for a night out on the town. Complete the look in platform block heels and earrings!

    Fit & Features

    • Leopard print, stretchy mesh fabric, sewn-in knit lining
    • Spaghetti straps
    • Side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5696

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Night Out

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine In The Night Ombre Rhinestone Wedges

    Step out in style and sparkle all night long in these ombre rhinestone wedges! The square toe and dual puffy straps adorned with ombre rhinestones offer a unique and trendy look. The wedge heel and faux leather footbed provide comfort while the satin material trim adds a touch of luxury! Complete the look with a rhinestone handbag.

    Fit & Features

    • 4" Wedge heel
    • Ombre rhinestone embellishments
    • Square toe
    • Puffy wide straps
    • Satin material trim
    • Faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-0360

    Category Name: Night Out

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Energetic Charm Abstract Mesh Crop Top

    Bring an energetic charm in this abstract mesh crop top wherever you go! The top boasts a classic silhouette with a crew neckline, short sleeves, and a fitted cropped hem on stretchy sheer mesh fabric. Complete the look in cargo pants.

    Fit & Features

    • Abstract print, sheer mesh fabric, stretchy
    • Crew neckline
    • Fitted cropped hem
    • Runs true size

    Style Number/Barcode: 06001-5228

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Kiss Metallic Stiletto Heels

    Wrapped in whimsical inspiration, these metallic stiletto heels are a major showstopper! Showcasing a square toe and rhinestone embellished toe and spiral ankle straps adorned with delicate butterfly decor. Complete the look with a clutch for a birthday party!

    Fit & Features

    • 4" Stiletto heel
    • Metallic material
    • Rhinestone straps, butterfly decor
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4749

    Category Name: Night Out

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Tequila Short Sleeve Crop Graphic Tee

    This short sleeve crop graphic tee is perfect for those who love to live life with a little bit of spice. With its crew neckline and cropped hem, this tee is both trendy and comfortable. And don't forget the fun front graphic and script that reads "If You're Going To Be Salty, Bring The Tequila!" Complete the look in a sleek mini skirt.

    Fit & Features

    • Stretchy knit fabric
    • Front graphic, script "If You're Going To Be Salty, Bring The Tequila"
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1800

    Category Name: Night Out

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Off-The-Shoulder Crop Top

    Is it hot in here or is it just you in this flirty off-the-shoulder crop top? Perfect for warmer days, this top features short-sleeve cuffs, an adjustable drawstring bust with a center slit accent to bare more skin! Complete the look in denim jeans and a choker for casual plans.

    Fit & Features

    • Stretchy rib knit fabric
    • Adjustable drawstring bust
    • Center front slit accent
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1803

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hustle Crew Strapless Tube Graphic Crop Top

    Feel fierce and fly in this graphic tube crop top! The strapless neckline and pointed crop hem add a touch of sexiness, while the front graphic with the script "Hustle Crew" inspires you to keep hustling. Complete the look in denim shorts for casual plans!

    Fit & Features

    • Stretchy knit fabric
    • Strapless neckline
    • Front graphic with the script "Hustle Crew"
    • Pointed cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1802

    Category Name: Night Out

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delicate Perfection Ribbon Bow Knit Tank Top

    Everyone will admire your chic sense of style in this adorable knit tank top perfect for dressing up your favorite bottoms! The square neckline is adorned with a delicate ribbon and bow trim, while the fitted crop hem and tank shoulder straps give it a stylish and flattering look. Complete the look in a denim skirt.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Square neckline, tank shoulder straps
    • Ribbon and bow trim
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-1980

    Category Name: Night Out

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Fierce Trendsetter Leopard Mesh Crop Top

    Treat your trendsetting self to this fierce leopard mesh crop top perfect for everyday styling! Featuring cap sleeves and a crew neckline, this top is perfect for making a statement. The cropped hem and sheer mesh fabric with a bold leopard print will have you standing out from the crowd. Complete the look with a bralette and high-rise jeans for a concert or casual party!

    Fit & Features

    • Sheer mesh fabric, leopard print
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5227

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Distinct Cutie Tie-Back Chiffon Crop Top

    Everyone will take notice of how cute you look in this chiffon crop top - perfect for brunch or day dates! Crafted from chiffon fabric, this top features adorable puff short sleeves, a flattering scoop neckline, and a ruched bust for added charm. The cropped hem and tie-back straps add a stylish touch. Complete the look in trendy denim jeans and heels.

    Fit & Features

    • Chiffon fabric, no stretch
    • Puff short sleeves
    • Tie-back straps
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2458

    Category Name: Night Out

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Silhouette Ruched Bodycon Mini Dress

    Sleek and smooth, this bodycon mini dress serves curves for days! Crafted from a soft double-lined knit fabric that fits like a glove, this dress features a square neckline adorned with adjustable spaghetti straps, side ruched seams to accentuate your figure along the bodycon silhouette, and a flattering mini-length hem. Complete the look with mules and a crop jacket.

    Fit & Features

    • Soft knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5683

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sexy Sensation One-Shoulder Corset Bodycon Mini Dress

    A sexy mini dress features a one-shoulder neckline, a sheer fitted long sleeve, and a sheer corset bodice with trim. Flaunt your figure in the bodycon mini-length silhouette perfect for styling with heels. 

    Fit & Features

    • Crepe fabric, partial lining, moderate stretch
    • One-shoulder neckline
    • Sheer fitted long sleeve
    • Back zipper and hook-eye closure
    • Sheer corset bodice with trim
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5587

    Category Name: Night Out

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Fantasy Plunge Halter V-Neck Mini Dress

    You'll always have a good time in this sleeveless mini dress for a sultry style out on the town! The halter plunge V-neckline and open back will turn heads, while the mesh tie straps add a touch of playfulness the bodycon fit and mini-length hem accentuate your curves and make you feel irresistible. Complete the look in stiletto heels.

    Fit & Features

    • Crepe fabric, bust lining, moderate stretch
    • Halter plunge V-neckline, mesh tie straps
    • Open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5586

    Category Name: Night Out

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Baddie Strapless Cutout Woven Crop Top

    Let this cutout crop top show off what a major baddie you are! Designed with a structured woven fabric, this crop top features a strapless sweetheart neckline with a center V-wired design to accentuate your bust, and asymmetric seams leading to small side cutouts for a hint of skin. The cropped hem and form-hugging fit will give you that snatched silhouette. Style with the matching maxi skirt and sleek stiletto heels!

    Shop Matching Bottoms: Major Baddie High Waist Belted Woven Maxi Skirt

    Fit & Features

    • Non-stretch woven fabric with lining
    • Strapless sweetheart neckline with V-wired design, no-slip strip
    • Asymmetric seams and side cutouts
    • Back zipper with hook and eye closure
    • Cropped hem
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06003-2449

    Category Name: Night Out

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty And Adorable Strapless Lace Bow Floral Skater Dress

    Flirty and adorable, this floral skater dress makes the sweetest impression at showers or birthdays! Featuring a sweetheart neckline with delicate lace trim and a charming bow, this dress is sure to turn heads. The padded bra cups provide a perfect fit, while the skater silhouette and mini-length hem add a touch of playfulness. Complete the look with earrings and strappy heels.

    Fit & Features

    • Floral print, chiffon fabric lined with woven
    • Strapless sweetheart neckline
    • Lace trim and bow
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3359

    Category Name: Night Out

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Baddie High Waist Belted Woven Maxi Skirt

    Let this belted maxi skirt show off what a major baddie you are! Designed with a structured woven fabric, this maxi skirt features a high waist with a double belted front design and cargo side pockets for a trendy look. The maxi-length hem is accented with a chic back slit detail. The form-hugging silhouette will showcase your stunning curves. Style with the matching crop top and sleek stilettos!

    Shop Matching Top: Major Baddie Strapless Cutout Woven Crop Top

    Fit & Features

    • Woven fabric
    • High waist
    • Maxi-length hem with back slit
    • Form-hugging fit
    • Double belt design
    • Cargo side pockets
    • Runs true to size

    Style Number/Barcode: 06401-0659

    Category Name: Night Out

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serves You Tight Wrap Faux Leather Skort

    So tight and so nice! This faux leather skort serves major allure to your evening out. It features a high-rise waist with a flirty pleated side seam that creates the wrap front design, a flattering bodycon silhouette, and a mini-length hem with shorts lining. Complete the look in a sexy bustier and heels!

    Fit & Features

    • Faux leather fabric with stretch, shorts lining
    • High-rise waist
    • Side pleated seam
    • Wrap-front design
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1141

    Category Name: Night Out

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Fate Pattern Nylon Fishnet Tights

    It must be fate for you to have these alluring nylon fishnet tights! Wrap your legs in these simply sexy tights featuring a comfortable high-rise waistband and a circle pattern that elevates every outfit. Complete the look with a ring set for a dressy occasion!

    Fit & Features

    • Nylon fishnet fabric
    • High-rise waistband
    • Circle pattern
    • Soft, stretchy, and comfortable

     

    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: 07306-0329

    Category Name: Night Out

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking Bold Faux Sheer Lined Floral Lace Tights

    Embolden your look in these striking lace tights to add that something special! Featuring a comfortable high-rise waistband and a delicate floral lace pattern for a gorgeous allure while the faux sheer lining offers coverage. Complete the look with a pretty hair headband for a semi-formal party!

    Fit & Features

    • Floral lace material, faux sheer lining
    • High-rise waistband
    • Soft, stretchy, and comfortable

     

    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: 07306-0327

    Category Name: Night Out

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale