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.

  • Major Glam Status Rhinestone Chain Belt

    Add major glam status to your chic 'fit by layering on this gorgeous belt! It features a rhinestone adorned interlocking O-ring design with a chain link and adjustable lobster clasp closure. Pair this over a sleek satin dress to add some sparkle.

    Fit & Features

    • Rhinestones
    • Interlocking O-ring design
    • Chain link
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-0246

    Category Name: Night Out

    Price: $10.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Stunner Peep Toe Stiletto Booties

    Yes babe, you'll be the stylish stunner of your trendy squad in these fab stiletto booties! They feature an almond-shaped peep toe, an inner zipper closure, a sleek stiletto heel, and a smooth faux suede material with an all-over leopard print. Pair these booties with a tie waist romper for a girl's night.

    Fit & Features

    • Above the ankle design
    • Almond-shaped peep toe
    • Inner zipper closure
    • Stiletto heel
    • Faux suede material
    • Leopard print

    Style Number/Barcode: 07403-1217

    Category Name: Night Out

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Satin Pleated Mini Dress

    Create stunning looks in this sleek satin mini dress. It features spaghetti straps, a V neckline, pleated detailing, and a mini length, asymmetric tulip hem with a curve-hugging fit. Pair this dress with a sparkly rhinestone choker necklace and strappy heels for a night out.

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Pleated detailing
    • Asymmetric tulip hem
    • Short, form-hugging fit
    • Satin-like fabric with moderate stretch

    Style Number/Barcode: 05103-3734

    Category Name: Night Out

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Leopard Print Burn Out Crop Top

    Keep your everyday look trendy and on point in this sultry crop top! It features a V neckline, long blouson sleeves with cinched hems, an open back with a tie back accent, and a cropped, form-hugging fit. The knit fabric has an all-over leopard print burn out pattern for a chic vibe. Pair this top with mom jeans and strappy heels.

    Fit & Features

    • V neckline
    • Long blouson sleeves with cinched hems
    • Open back
    • Tie back detail
    • Cropped
    • Form-fitting style
    • Sheer leopard print burn out knit fabric, unlined 

    Style Number/Barcode: 06001-3061

    Category Name: Night Out

    Price: $13.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Floral Lace Tie Front Crop Top

    Get those flirty vibes in this adorable floral lace crop top! It features long fitted sleeves, a V neckline, a tie front detail, and a cropped, form-hugging fit. Pair this top with a faux leather mini skirt and strappy heels for date night with bae.

    Fit & Features

    • Long fitted sleeves
    • V neckline
    • Tie front detail
    • Cropped
    • Form-fitting style
    • Sheer floral lace woven fabric
    • Moderate stretch

    Style Number/Barcode: 06204-0754

    Category Name: Night Out

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Vixen Snake Print Stiletto Heel Boots

    Vamp up your look with head-turning boots that command attention. The boots feature a below the knee fit, a snake print, a pointed toe, and a stiletto heel. The boots are composed of brushed faux leather material. The interior is lined and lightly padded for comfort. Complete the look with a ribbed mini dress. 

    Fit & Features

    • Below the knee fit
    • Snake print
    • Pointed toe
    • Stiletto heel
    • Brushed faux leather exterior
    • Lined, lightly padded

    Style Number/Barcode: 07402-0294

    Category Name: Night Out

    Price: $18.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back to Basics Faux Suede Platform Heels

    Bring it back to basic in heels that go with all your favorite fits'. The heels are perfect to wear for that upcoming bridal shower or for a date night with bae. The heels feature a solid neutral hue, an adjustable ankle strap, criss-cross straps over the toe, a wide platform, and a block heel. Complete look with a curve-hugging bandage bodycon.

    Fit & Features

    • Solid neutral hue
    • Open Almond toe
    • Criss-cross straps over the toe
    • Wide platform
    • Block heel
    • Faux suede material

    Style Number/Barcode: 07401-2611

    Category Name: Night Out

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Glam Faux Leather Quilted Moto

    Make it edgy and glam with this chic moto jacket! It features an asymmetrical zipper front, zippered side pockets, long sleeves with zippered closures, and a cropped belted waist. The jacket is composed of a faux leather fabric that offers a form-hugging fit. Complete the look with a bustier and skinny jeans.

    Fit & Features

    • Collared neckline with stud button detailing
    • Asymmetrical zippered front
    • Long sleeves with zippered closures
    • Zippered side pockets
    • Cropped belted waist
    • Quilted faux leather fabric with a smooth lining
    • Form-hugging fit 

    Style Number/Barcode: 06204-0749

    Category Name: Night Out

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Sheer Lace Bodysuit

    Sultry and chic will be your vibe in this sexy bodysuit! It features bungee spaghetti straps that lead to a cross back, a scoop neckline, and is composed of sheer lace fabric with a lining at the bust. Pair this form-fitting bodysuit with faux leather pants and clear heeled mules for a night out.

    Fit & Features

    • Bungee spaghetti straps
    • Cross back
    • Scoop neckline
    • Thong bottom with dual snap button closures
    • Sheer lace fabric with moderate stretch
    • Lined bust
    • Form-fitting style

    Style Number/Barcode: 06001-3055

    Category Name: Night Out

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Girl Peep Toe Stiletto Booties

    Yes girl, showcase your edgy side in these trendy stiletto booties! They feature a pointed peep toe, a lace-up front, a sleek stiletto heel, and a faux leather material. Pair these booties with your fave pair of skinny jeans to elongate your legs for a flattering silhouette.

    Fit & Features

    • Above the ankle design
    • Pointed peep toe
    • Lace-up front
    • Inner zipper closure
    • Stiletto heel
    • PU material

    Style Number/Barcode: 07403-1211

    Category Name: Night Out

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Babe Ruched Midi Dress

    Yes babe, show off your gorgeous curves in this figure-flattering midi dress. It features thick and thin spaghetti straps, a cowl neckline, ruched detailing, and a mid-length, form-hugging fit. The knit fabric offers plenty of stretch for comfortable wear. Pair this dress with clear mules and a sleek clutch.

    Fit & Features

    • Thick and thin spaghetti straps
    • Cowl neckline
    • Square back
    • Ruched
    • Mid-length, form-fitting style
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0930

    Category Name: Night Out

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Night To Remember Mesh Mini Dress

    Make your night a memorable one in a dress that brings chic deets! The dress features a sleeveless V-neckline, vertical princess seams at the bust, a sheer sexy mesh inset at the waist with piping details, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules and a rhinestone clutch.

    Fit & Features

    • Sleeveless V-neckline
    • Vertical princess seams at the bust
    • Unlined mesh inset at waist
    • Piping details
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch 

    Style Number/Barcode: 05103-3718

    Category Name: Night Out

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Red Chic Faux Leather Stiletto Booties

    Sound off the alarm with booties that bring chic appeal! The booties feature a mid-calf fit, a lace-up front, a peep toe, and a sleek stiletto heel. The booties are composed of a faux leather material. Complete look with a bodycon.

    Fit & Features

    • Mid-calf fit
    • Lace-up front
    • Peep toe
    • Inner zipper closure
    • Stiletto heel
    • Faux leather material 

    Style Number/Barcode: 07403-1212

    Category Name: Night Out

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Add Some Sass Backless Bodysuit

    Add some sass to your style with this trendy bodysuit! It features a crew neckline, long fitted sleeves, an open back, and a thong bottom with dual snap button closures. The lightweight knit fabric offers plenty of stretch and showcases an all-over snake print. Complete your look with a faux leather skirt and strappy heels for a girl's night out.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Backless
    • Thong bottom with dual snap button closures
    • Form-hugging fit
    • Knit fabric with plenty of stretch
    • Snake print

    Style Number/Barcode: 06001-3054

    Category Name: Night Out

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glitter Knit Stiletto Sock Booties

    Add some shine to your classic booties this holiday season with these glitter knit sock booties! They feature a fitted above the ankle-design, pointed toe, stiletto heel, and inner zipper closure. Pair these booties with a faux leather mini skirt for an edgy-chic party look.

    Fit & Features

    • Fitted above the ankle design
    • Pointed toe
    • Stiletto heel
    • Inner zipper closure
    • Glitter knit material

    Style Number/Barcode: 07403-1210

    Category Name: Night Out

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut It Out Faux Leather Stiletto Heel Booties

    Strut it out in chic booties that bring those trendsetter vibes to your outfit! The booties feature a mid-calf fit, a lace-up front, an inner zipper closure, and a sleek stiletto heel. Complete look with a bodysuit and mini skirt for the perf date night look. 

    Fit & Features

    • Mid-calf fit
    • Lace-up front
    • Inner zipper closure
    • Peep toe
    • Stiletto heel
    • Faux leather material

    Style Number/Barcode: 07403-1213

    Category Name: Night Out

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Beauty Satin Mini Dress

    Showcase your beauty in this chic and sleek satin mini dress that is perf for a night out with the girls! It features a sleeveless bodice, spaghetti straps, a square neckline, front ruching, and a mini-length, curve-hugging silhouette with a drawstring at the hem. Complete the look with heels and a stylish clutch.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Back zipper closure
    • Front ruching, drawstring at the hem
    • Short, form-hugging fit
    • Satin fabric
    • Runs true to size

    Style Number/Barcode: 05103-3720

    Category Name: Night Out

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Faux Leather Skinny Pants

    Strike a pose in skinny pants that offer that sleek streamlined look for your night out outfits. The pants feature a single button closure with zipper closure, side pockets, belt loops, and a skinny leg with cropped tapered hem. The pants are composed of a faux leather fabric that offers a form hugging fit. Complete look with a crop top. 

    Fit & Features

    • High rise fit
    • Belt loops
    • Single-button with zipper closure
    • Side pockets
    • Skinny leg with a cropped tapered hem
    • Faux leather fabric
    • Form hugging fit

    Style Number/Barcode: 06402-0293

    Category Name: Night Out

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Belted Baddie Faux Leather Moto Jacket

    Show off your baddie side with a jacket that can be layered to create chic night out outfits. The moto jacket features a collared neckline, an asymmetrical zipper front, faux zippered pocket, faux small pocket, side pockets, and a belted waist. Complete look with a ribbed midi dress and combat boots.

    Fit & Features

    • Collared neckline
    • Asymmetrical zippered front
    • Faux zippered pocket
    • Faux small pocket with snap button closure
    • Side pockets
    • Long sleeves, belted waist
    • Lined faux leather fabric, form-hugging fit, slight stretch 

    Style Number/Barcode: 06204-0740

    Category Name: Night Out

    Price: $20.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ivy Embroidered Sequin Mini Dress

    Special Occasion 

    A sequin mini dress will bring the shimmer to your special occasion and radiate from every angle. The Ivy formal mini dress features a wide round neckline, sheer long fitted sleeves, a stunning scoop back, and a mini-length silhouette with an asymmetrical hem. The Ivy dress is composed of a lined mesh fabric adorned with sequins throughout. Complete the look with a dainty rhinestone bracelet with a pair of chrome heels.

    Fit & Features

    • Wide round neckline
    • Sheer long fitted sleeves
    • Scoop back, zipper closure
    • Mini-length asymmetrical hem 
    • Sequin embroidery
    • Sheer mesh fabric, knit lining, moderate stretch
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-0536

    Category Name: Night Out

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Stunner Faux Leather Crossbody

    Create a head-turning statement in a crossbody that brings the chic factor to your look! The crossbody features a large rounded body with scrunched detailing, chunky chain link handles and composed of a faux leather material. Complete look with a long sleeve mini dress and mules. 

    Fit & Features

    • Large rounded body 
    • Scrunched detailing
    • Chunky chain link handles
    • Detachable shoulder strap 
    • Faux leather material 

    Style Number/Barcode: 07203-0471

    Category Name: Night Out

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glitzy Girl Rhinestone Mules

    Bring all the glitz and shine with these heeled mules! They feature an open square toe, two bands with rhinestone detailing and a block heel. Pair them with a mini dress and a matching rhinestone bag.

    Fit & Features

    • Open square toe
    • Double bands with rhinestone detailing
    • Block heel
    • Runs true to size

    Style Number/Barcode: 07401-2603

    Category Name: Night Out

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Chic Snake Print Shoulder Bag

    Add a trendy chic vibe to your everyday look with this snake print shoulder bag! It features a top zipper closure, a removable chunky chain link shoulder strap, and an included longer adjustable strap to convert it to a crossbody. Pair this bag with a basic tee and a faux leather skirt for a luxe look.

    Fit & Features

    • Top zipper closure
    • Removable chunky chain link shoulder strap
    • Included longer adjustable strap
    • Interior pockets
    • Allover snake print
    • Brushed faux leather material with a woven interior

    Style Number/Barcode: 07203-0466

    Category Name: Night Out

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All That Glam Rhinestone Crop Top

    Bring the glitz in a glam crop top! The top features a sleeveless cowl neckline, rhinestone embellished straps, and a cropped hem. The back features a daring open back with a double row of back ties. Complete your look with faux leather pants and mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Rhinestone embellished straps
    • Cropped hem
    • Open back with dual back ties
    • Smooth knit fabric with plenty of stretch
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-3438

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance